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Author: OrmontUS   😊 😞
Number: of 198 
Subject: Brooklyn - more than you ever wanted to know
Date: 06/02/26 10:50 PM
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A small snippet from "Take the High Road - A Primer for the Independent Traveler" (https://www.amazon.com/dp/B00V7C2L9S)

Enjoy,
Jeff

Brooklyn, New York, USA

There is a walking tour which covers many of the places discussed in this piece following afterwards

After documenting cities in over 100 countries, it suddenly dawned on me that I hadn’t taken the time to discuss the borough of Brooklyn in New York City, my fair city.

Well, that should be easy, I thought – after all, I’ve lived here my whole life (well, at least the half of my life that I didn’t spend traveling 😊). Well, it turns out not so easy. Not only is Brooklyn (by population) the fourth largest city in the country (if it seceded from NYC), but its complex geography of demographic diversity, based on its being the recipient of immigrants since the days when Dutch was spoken here.

Before we get to the good stuff, Newark Airport, is the most awkward and expensive (due to both distance, tolls and crossing state lines) of NYC’s three airports for us. Uber came to the rescue, but finding the designated location is a bit confusing. (Arrivals is on the second floor. When you leave the secure area, head all the way to the left to a pair of glass-doored elevators. Take one down to the first floor, walk out the door of the terminal, cross the road to the divider and head to the right to the signs indicating “Uber” – about 20 yards past the Lyft ones). Both JFK and LaGuardia airports have flat-rate taxi fares to Manhattan.

In 1883, the Brooklyn Bridge was opened connecting the cities of Brooklyn to New York City replacing the Fulton Ferry – previously the only means to cross between the two islands. Brooklyn had an advantage of having a large population which could feed the factories of Manhattan and the disadvantage of using artesian well water which tasted of sulphur. NYC had fresh spring water feeding their water supply. Originally, Brooklyn was a separate city from New York City. It had its own City Hall (now Borough Hall), its own opera house, the Brooklyn Academy of Music (now known as BAM), its own “central park” – Prospect Park and its own world-class museum being constructed – the Brooklyn Museum, whose construction was aborted at only a quarter of its originally planned size when the two cities combined.

The Williamsburg Bridge was completed in 1903 and the Manhattan Bridge in 1909. Both could carry subway trains which made it convenient for those living in Manhattan’s crowded slums to move to Brooklyn as well as Brooklyn’s population to easily reach Manhattan’s factories.

As national groups of immigrants spawn children who become educated, they are geographically replaced by new cadres from elsewhere in the world. Bay Ridge historically had a large Norwegian population and today has significant Arab, Middle Eastern, and Mexican communities. Bensonhurst has evolved from historically Italian-American to increasingly Chinese-American while still retaining Italian legacy businesses and Brighton Beach and Manhattan Beach (yes, in Brooklyn) have become largely populated by those originating in various former Soviet Republics. In each of these cases, the banks, newspapers, local shops and restaurants are reflections of those found “back home” rather than those traditionally found in the US.

Neighborhoods are generally defined by a single street and you can literally cross the street from Mexico to Lebanon, walk a few blocks and cross into Shanghai. For a “foodie” there is no place like this in the world as the local restaurants are generally inexpensive and authentic – as there are virtually no tourists and the locals demand food exactly as prepared back in the “old country”. Similarly, items typically only found “back home” are stocked in the ethnic supermarkets and grocery stores as well as in shops selling items we travelers would be tempted to call souvenirs, but to the locals are simply the products they have grown used to before coming to the US. So, knowing where the boundaries of the neighborhoods lay is important to experience this phenomenon.

A few of the current ethnic concentrations:

Bushwick, Brownsville, East New York Caribbean
Williamsburg, Boro Park, Crown Heights Hasidic Jews
Northern Bay Ridge, Cobble Hill Arabs
Sunset Park, Gravesend, Bensonhurst Chinese
Gravesend Syrian Jews
Gravesend, Homecrest, Midwood European Jews
Bay Ridge, Gravesend Mexican
Brighton Beach, Manhattan Beach, Sheepshead Bay Russian/Ukrainian, etc.
Flatbush, Brighton Beach Indian/Pakistani/Bangladeshi
Greenpoint Polish
Dumbo, West Greenpoint/Williamsburg, Park Slope Yuppie cool kids

The list could go on and on – basically listing groups from nearly every country in the world.

Brooklyn’s unique sights/sites fall into a number of major categories. One of the most unique genres could loosely be called “parks”.

First and foremost, would be Prospect Park. Designed and constructed over a thirty-year period (1865-1895) by Frederick Law Olmsted and Calvert Vaux, the masterminds behind Central Park, Prospect Park, on the site of the Revolutionary War’s Battle of Brooklyn, was transformed into a premiere destination for Brooklyn visitors and residents alike. Many landscape historians consider Prospect Park to reflect a more mature evolution of Olmsted and Vaux’s park design philosophy. Its zoo is now modernized into habitats and no longer has its old-fashioned menagerie of lions, tigers, bears and so on in their tiny cages. The park also contains the LeFrak Center Ice Skating Rink at Lakeside.

Just north of the park, Soldiers and Sailors Memorial Arch (reminiscent of the Arc de Triumph in Paris) was constructed on “Grand Army Plaza” commemorating the Union Army which participated in the US Civil War. The City Planners created a star of major “Parkways” radiating from this point which (more or less) included Eastern Parkway, Ocean Parkway (both of which had lawns and pedestrian esplanades/bridle paths running their length) and Flatbush Avenue. Facing the Grand Army Plaza is the Brooklyn Public Library’s Central Library – an architectural masterpiece in its own right.


Across Flatbush Avenue from Prospect Park is the magnificent Brooklyn Botanic Gardens which includes one of the US’s oldest and most ornate Japanese gardens.

Adjacent to the Botanic Gardens is the magnificent Brooklyn Museum. If it wasn’t for the fact that NYC was also home to the larger Metropolitan Museum of Art, it is likely that the Brooklyn Museum would be its primary Art Museum – and should be on every art-lover’s must-see list.

A few blocks from Prospect Park to the west (south of the interesting Park Slope
area) is The Green-Wood Cemetery. Brooklyn has been home to thousands of famous celebrities. While it has a number of huge cemeteries, Green-Wood Cemetery is to Brooklyn what Père Lachaise Cemetery is to Paris. The list of “must-see” graves includes those of Leonard Bernstein, Louis Comfort Tiffany, Boss Tweed, DeWitt Clinton, Elias Howe, Peter Cooper and Horace Greeley to name a small handful.

Heading north, up Flatbush Avenue towards the Manhattan Bridge, we see the modernistic Barclays Center, home of the Brooklyn Nets basketball team and venue for concerts. Just north of the Barclays Center is the Brooklyn Academy of music and downtown Brooklyn’s Fulton Street commercial area. A block or two further brings you to Brooklyn Technical High School (the building with the massive radio antenna on its roof). This massive high school of 6,000 students (which I was lucky enough to attend in my youth) is the largest, and one of the country’s best-known STEM (science/technology/engineering/math) schools in the nation.

Across Dekalb Avenue, on the north side of the school, is Fort Greene Park, a burial place used by the British during the Revolutionary War to inter American captives who died while kept in prison ships. Heading along Dekalb Avenue and crossing Flatbush Avenue (back onto Fulton Street) will let you peruse the renovated commercial district of downtown Brooklyn (in part, created out of the massive theatres of the past) and continue on to the multi-denominational Brooklyn Tabernacle (at 17 Smith Street on Fulton Mall).

Nearby, at 99 Schermerhorn St, is the New York Transit Museum which shows off the amazing history of NYC’s mass transit system.

The popular Brooklyn Heights neighborhood is west of there. Along the western edge of the neighborhood is the Brooklyn Heights Promenade, a park constructed over the double level Brooklyn-Queens expressway and which offers incredible harbor views.

From there, it’s a short walk to the pedestrian entrance to the Brooklyn Bridge and the opportunity to walk across this amazing structure all the way to Manhattan (make sure to take a camera).

Back on the Brooklyn side, head down towards the Hudson River to the neighborhood of Dumbo (Down Under the Manhattan Bridge Overpass). This residential district made out of old warehouses and commercial buildings is known for incredible views. Walk along the waterfront and you’ll find Jane's Carousel, St. Ann's Warehouse and the Empire Fulton Ferry stop of the water taxis which play the harbor and river.

Well, that’s the north end of Brooklyn; now let’s head south.

Few think of New York City as a beach resort, but for well over a century, Coney Island and its adjacent Brighton Beach have been exactly that. Lined with its Riegelmann Boardwalk, in pre-air conditioning days, when both the temperature the humidity got high on weekends or holidays, over a million people would show up to take a dip in the water. While the beach was a few miles long and the sand about 100 meters between the Boardwalk and the water, a million people creates quite a crowd and you could walk from the boardwalk to the water, on people’s beach blankets, without having to touch the hot sand with your feet.

Along the Boardwalk (at about West 8th Street) is the New York Aquarium. While far from being Sea World, it is a decent aquarium and worth a visit if you are already in the neighborhood.

In the old days, Coney Island was known for its multiple vast amusement parks. There is a vestige of one called Luna Park which still contains the vintage “Wonder Wheel” (a Ferris Wheel) where half the cars are movable on rails and simulate the cars swinging off the wheel as it turns. The “Parachute Jump” is no longer in use, but has been retained as a symbol of the past. The “Cyclone” an antique wooden roller coaster is still scaring the daylights out of the young a block from the beach. Also nearby is the original location of Nathan’s a VERY informal restaurant known for its hot dogs and all things fast-food (prices are now higher than I remember from my youth).

Some other notable places to search out include:
Brooklyn Children's Museum (145 Brooklyn Ave.) Fantastic for kids
Brooklyn Brewery (79 N 11th Street) Tours and tasting of some of the best US beers
Dyker Heights Christmas Lights (1072 80th Street) The most incredible (seasonal)

For some real unusual places, peek at the ones listed here:
https://www.atlasobscura.com/things-to-do/brooklyn...

Walking, Bus, Subway tour of Brooklyn (NYC Tour 1)

NOTE: NYC has recently installed panels to allow most credit cards with a “chip” (or their OMNY phone app) to be used to pay at all subway stations and on buses. The phone app (or for now, the still existing Metrocards) can be used for “time” fares (one day or one month)

NYC Subway Map: https://new.mta.info/maps

Brooklyn Bus Map: https://new.mta.info/maps

While the following information on “Metro Cards” is still in effect, NYC’s transit system – both buses and subway system – now accepts tap-type credit cards as well as payment though the “OMNY” mobile phone app.

Pick up a 7-day Metro Card at the beginning of your trip. If you are only staying a couple of days, it is probably cost effective to put $10 or $20 on a Metro Card (you get a bonus either way) and keep refilling it at the vending machines in the stations on an “as-needed” basis. These are available at all subway stations either at change booths (cash only) or in vending machines which take cash and credit/debit cards These will give access to all the public busses and subway systems. The one-week cards cannot be used again at the same subway station or the same bus route for at least 18 minutes. The pre-loaded cards will give you a free transfer from the subway to a bus within two hours of first use.

Be aware that there are Chinese, Arabic and Pizza lunches pointed out (as well as a couple of desert places), so you’ll either have to be selective, and eat small portions in each or gorge yourself throughout the day.

This is going to be very abbreviated because Brooklyn is huge (and as a standalone city would be the fourth largest in the US)

1) Take the DOWNTOWN A or C train from 8th Ave and 14th Street near Meat Packing district to Chamber Street

2) Walk east down Chamber St. through the Tribeca neighborhood to City Hall (where the Mayor has his office). The court houses that you pass as you continue walking past Broadway were banks until they were wiped out during the stock market crash of 1929 and the subsequent bank closures through 1931. The huge building with the gold statue on top directly ahead of you is the NYC Municipal Building and houses administrative offices. The modern building that you can see through the archway in the Municipal Building is the New York Police Department headquarters.

3) At the end of Chamber Street, as you make a right turn around the back of City Hall, ask a cop (there will be no shortage of them around there – if you cannot find one, the entrance is directly across the street “Park Row”) where the pedestrian entrance to the Brooklyn Bridge is. Walk across the bridge (a little under two kilometers) and make sure you have film in your camera – the walk will take about half an hour. Remember to look at the views of Manhattan over your shoulder (It is actually nicer to walk the bridge towards Manhattan, but I figured you would be too tired in the afternoon).

4) 1. Take the first exit off the Brooklyn Bridge pedestrian walkway. Note: There are two pedestrian exits when walking across the Brooklyn Bridge from Manhattan to Brooklyn. The first exit is the most direct route to DUMBO.

2. Take the path off the pedestrian walkway that bears to the left and slightly downhill as you face Brooklyn.

3. Follow the path to a small stairway . Go down the stairs to an underpass on Washington Street. The Washington Street underpass is about two blocks from Front Street in the heart of DUMBO.

4. Turn left and head down hill, toward the East River and Manhattan skyline. When you cross under the highway overhead, you will see the industrial buildings, shops and restaurants of DUMBO.

5) Look at the walking directions here: https://maps.google.com/maps?ie=UTF-8&gl=us&daddr=...

Notice Jacques Torres Chocolate Shop on Water Street to the left of the “B”. This is a world class place and a great place to stop for a hot (or frozen) chocolate and a piece of dark chocolate/almond bark. Across the street is a decent French bakery named Almondine which makes pretty good almond/chocolate croissants and cappuccino (the chocolate place is a better choice, but you might stop here anyway for its clean toilet). Continue down Water Street past the Chocolate shop, passing some ugly warehouses until you see a passageway to the right. This will take you to some of the most fantastic views of Manhattan. There is an antique carousel there if you are feeling like a kid again. Walk to the water and make a right walking under the Brooklyn Bridge and you’ll find a small beach on the river.

Walking in the other direction will take you past the “River Café” (owned by the same people as the “Water Club” in Manhattan and famous for the view and small/expensive portions like their sibling). There is a good ice cream shop in the old ferry building just past the restaurant (but you may want to hold off as the desserts will be better later on). Continue to walk along the shore (passing a Water Taxi terminal where you can take a boat back to Manhattan) and into “Brooklyn Bridge Park. This is a brand new (still under construction) park which features a pool, canoeing, fishing and other cool stuff. Up above you is an historical neighborhood (Brooklyn Heights) which would be worthwhile walking through next time you are in the neighborhood.

After you’ve had your fill of the park, backtrack to the the historic Brooklyn waterfront ice cream location and make a right up Cadman Plaza. You will pass a fairly famous pizza place named Grimaldi’s on your left. If it is empty, you can try their pizza, but if there is a line, just pass it by as there will be another chance at a great pizza (maybe better than here ) later on. Since it is a fairly long (partly uphill) walk, I’d recommend jumping on the B25 bus at the bus stop between Everit St. and Elizabeth St. Tell the driver that you want to transfer to the B41 bus towards Flatbush Avenue and he’ll let you off about five minutes later at Tillary Street (and hopefully point you towards the proper bus stop). While taking the subway would be faster, the bus ride might be more interesting.

Take the B41 bus to “Grand Army Plaza”. This is Brooklyn’s competitor to the Arc de Triumph and the large boulevards radiating from the plaza were going to be its Champs Elyse according to the original plan (derailed when Brooklyn joined NYC in 1900).
The Soldiers' and Sailors' Memorial Arch, a Civil War memorial designed by
John H. Duncan with sculptures by Frederick MacMonnies, stands at Grand Army Plaza in Brooklyn. The arch was built between 1889-92, commemorating Union forces that died in the Civil War. MacMonnies's huge quadriga sculpture on top was installed in 1898, and the two groups on the south pedestals representing the Army and Navy were added in 1901. The Brooklyn Daily Eagle reported on the arrival of the sculpture in this article: "Quadriga is here" (August 15, 1898).
The Grand Army of the Republic was a private veterans' association of former Union soldiers and sailors, founded in 1866. The organization disbanded in 1956, after the death of the last surviving Civil War veteran.

Touching the south side of the plaza are Prospect Park (designed by the same team who had previously built Manhattan’s Central Park, but improved on the design here), a large botanic garden with arguably the best Japanese garden in the US and the Brooklyn Museum, a world class institution – mainly art and anthropology. The large building in front of the arch is the main branch of the Brooklyn Public Library. The entranceway to Prospect Park is directly across from the Arch and taking a couple of minutes to walk inside might be fun.

OK, back to work. Walk back up Flatbush Avenue in the direction you came down, past the fountain and across Sterling Place (important to cross this street so you do not take the wrong subway). The station you are looking for is going to have indication signage for the “B” and “Q” trains and will be at the intersection of Carlton Avenue, 7th Avenue and Flatbush Avenue. Go to the platform heading “Downtown” or Towards Brighton Beach/Coney Island (opposite direction from Manhattan). Take whichever train comes first (the “B” is the express, but there will only be a few minutes difference, at worst, if you catch the “Q”. Take the train all the way to the Brighton Beach stop (as a reminder, it is the stop after Sheepshead Bay and will be about 15-20 minute ride).

Walk down the station steps. You want to be on the north-west corner of the rather large intersection (diagonally across from the large Chase bank branch (and more or less in front of a Walgreen’s pharmacy (Has a big red sign). You should walk towards Brighton 7th Street (if you see Coney Island Avenue, you’re heading in the wrong direction).

Keep walking (total distance will be about 1/2km) and keep your eyes open. Most people will be speaking Russian, the signage in the stores will be Russian and the food in the supermarkets (walk into a couple and browse around) will be Russian. Walk until you get to a very broad street named Ocean Parkway (this actually extends as far as Prospect Park and was part of Brooklyn’s original “grand plan”).

Do not cross Ocean Parkway, but instead, cross Brighton Beach Avenue by making a left and walking along Ocean Parkway. A couple of blocks further, you will see a ramp/stairs up to the Boardwalk which runs along the more than 5km of beach which makes up Brighton Beach and Coney Island Beach (actually one seamless beach). Make a right turn and take a walk along the Boardwalk. While the weather will likely be cool in October, visualize the beach packed with visitors on a hot summer weekend day. Ahead of you will be the Parachute Drop tower. When I was a kid, this was an amusement park ride (moved here from the 1939 NYC World’s Fair) which would drop people sitting on parachute supported seats. It shut down in the 1960’s I think, but has been refurbished as an iconic symbol.

There is a minor league baseball stadium next to it and, with the exception of the pretty cool “Wonder Wheel” (a Ferris wheel designed to have some of the cars swing out on rails as it turns), all of the rides are pretty lame now as the old (supreme) amusement parks all closed or burned decades ago. There’s a very good aquarium here as well.

There is a long pier, used by people fishing for fun, named Steeplechase Pier (Steeplechase was the name of one of the legacy amusement parks in the “old days”) as well. There is a famous hotdog stand a block inland from the named Nathan’s (dates from the early 1900’s and is the flagship of a chain of them), but I think we can do a bit better for lunch than a sausage. We are going to walk past the NY Aquarium (worth seeing on the next trip – better in the summer when they bring out the dolphins, but we have still got a lot of ground to cover) all the way to just past the Wonder Wheel and we’ll make a right at Stillwell Avenue.

About a block from the Boardwalk, across the street from Nathan’s, we’ll find the Coney Island subway station (actually elevated above ground). Also, if it is still running in October (It is closed for the winter), to your right is the “Cyclone” one of the old time wooden roller coasters – and certainly worthy of a ride.

As in any busy urban environment, remain aware of your surroundings, especially late at night.

Now’s when we’ll have that great pizza (or at least very good and pretty convenient). We will walk past the left hand side of the station crossing Mermaid Avenue to the next street – Neptune Avenue (not crossing it) and make a left turn. A block and a half later, on the left, at 1524 Neptune Avenue is a place called Totonno’s which looks like a bit of a dive, but makes good pizza.

Now walk back to the nearby train station you passed when you walked from the boardwalk.
There are a lot of different trains which congregate here, so we have to be careful to take the “N” train (towards Manhattan – no choice as it is the end of the line).

Now we are going to see how the patchwork of neighborhoods can make small distance seem worlds apart in Brooklyn.

Take the train to the 8th Avenue station (in Brooklyn – the stop after Fort Hamilton Parkway and about a fifteen minute ride). Walk down 8th avenue in the direction where the cross-street numbers decrease (north). You will find yourself in a neighborhood (Sunset Park) which, other than architectural details, is similar to what you might expect in Hong Kong or China. If you are in the mood for good dim sum (or ordering off of a menu), there is a good restaurant named Pacificana on the second floor of a building located at 813 55th Street (corner of 8th Avenue and a few blocks from the station).

If you feel like trying something else for lunch instead, head back to the subway station and continue on the Manhattan bound train one more stop to 59th Street. Now, cross to the opposite platform and take the “R” AWAY from Manhattan (towards 95th street) for two stops to 77th Street. You will come up above ground on 4th Avenue. Ask someone which direction is 3rd Avenue and walk to 7523 3rd Avenue (corner of 75th Street) to a Middle Eastern (technically Palestinian) restaurant named Tanoreen. My recommendation is to order a number of appetizers rather than main courses (what is known as a mezza). I can recommend most of them (but not their falafel which for some reason they tend to ruin). Make a point to try their muhammara – a roasted red pepper and walnut paste. Rather than have dessert there, cross 3rd Avenue and walk back to 7612 3rd Avenue to the Omonia Café – a very good Greek pastry shop and order one of their desserts (and maybe a Greek coffee – same as Turkish coffee, but do not call it Turkish in this establishment).

Another option is to take the train three stops (instead of two) and get off at 86th Street (and 4th Avenue). There is a local high fashion discount department store here named Century 21 (which has partially reopened following its COVID-era bankruptcy closure), but we are heading to 8221 3rd Avenue (between 83rd and 82nd Streets) to Le Sajj, one of Brooklyn’s better-regarded Lebanese restaurants (closed Mondays). This reasonably priced restaurant will make you feel like you’re in Beirut. All their food is great, but they have a couple of salad platters for two which are worth trying. Incidentally the Bay Root grocery store is a couple of blocks further up the street.

After you finish eating, at Tanoreen, cross 3rd avenue and continue walking past 4th Avenue to 5th Avenue (or simply walk a few blocks further up 5th Avenue, towards lower numbered streets, from Le Sajj). For a few blocks in either direction on 5th Avenue, you will find dozens of Arabic (mainly Lebanese and Syrian) grocery stores, jewelers, restaurants and a couple of good French pastry shops and so on. Though we are not going to go quite that far, once you cross 65th Street, 5th Avenue becomes almost entirely Hispanic (with an emphasis on Mexican) if you feel like some pretty authentic Mexican food.

Now we’ll walk back to 77th or 86th Street and 4th Avenue and duck back into the subway. We’ll take the “R” train UPTOWN (towards Manhattan) to 36th Street (5 or 6 short stops) and change to the “D” train heading back towards Coney Island (DOWNTOWN, so means changing platforms again). Take the “D” train four stops to 55 Street. You will be on 13th Avenue in the neighborhood of Borough Park.

Walk a few blocks up 13th Avenue through one of NYC’s Hassidic Jewish communities. While there are a few others which are somewhat more “intense” the point to this exercise is that, with the exception of the Russian neighborhood, all of the ethnic communities we are visiting are within a circle of about three kilometers. Walk into one of the bakeries (Weiss, for example, at 13th Avenue and 50th street) and ask for “a quarter pound of cheese ruggelukh” (phonetic, rather than usual spelling) and you’ll end up with a handful of very tasty small (and relatively unique) pastries.

Our last food/neighborhood stop. Get back on the same direction that you were heading (“D” train towards Coney Island) and head another two stops to the 71st Street station. We are heading to the corner of 70th Street and 18th Avenue (you will get out of the train somewhere between 15th and 16th Avenues, so it is a couple of block walk. This neighborhood is Bensonhurst (which was featured in the movie Saturday Night Fever).

We are heading to the Villabate Alba southern (Sicilian and Neapolitan) Italian pastry shop (at 7001 18th Avenue) that is excellent and widely respected locally (the famous Ferrara’s pastry shop on Grand Street in Little Italy only wishes their pastries were as good as in this shop). This remains a very popular neighborhood pastry shop where waits are common. While the cannoli’s are filled while you wait, this is the place to get gelato and Italian ices better than you can imagine (and well worth saving room for even if you passed earlier dessert options). They also have good espresso/cappuccino. Walking a couple of blocks up 18th Avenue (I think between 71st and 72nd Streets) brings us to a small, but fantastic store selling Italian products.

OK, I guess all good things come to an end and it is time to head back to the Meat Packing District. We head back to the “D” train and this time take it UPTOWN towards Manhattan. We pick it up at 71st Street near 16thAvenue. We are going to take it all the way to the West 4th Street/Washington Square station in Manhattan and then change to the “A”, “C” or “E” trains (any will do) heading uptown (will have to change platforms) for one stop to 14th Street and 8th Avenue at which point you’ll come up for a well-deserved rest 


Walking tour of downtown Manhattan and Williamsburg Brooklyn (NYC Tour 2):

Recommended book to read about the neighborhood we’ll be discussing (as well as a couple of others like Union Square and Gramercy Park) in the context of a good murder mystery: “The Alienist” by Caleb Carr

I’ll try to put together the second route I described. I find the key to seeing a large city is to break it into areas of interest, or at least a path linking a number of interesting items. Otherwise, you end up wasting a lot of time zig-zagging from place to place and missing a lot that you might find interesting.
Some “truisms”:

There are many fine places to eat in Manhattan and many mediocre ones (including many that tourists seem to flock to). They are all (with the exception of some of the ethnic places in the East Village and Alphabet City, and of course fast food places) expensive. There are a number of Indian restaurants on 2nd Avenue in the East Village which are reasonably priced. There is also a popular Moroccan place named Mogador (101 St. Marks Place, http://www.cafemogador.com/contact)
if you find yourself in that part of town (for lunch – the neighborhood is busy and energetic at night, though—as in any nightlife district—normal urban awareness is recommended).

Warning – this is a REALLY long walk, so wear comfortable shoes:

A good walking tour a few hours in duration from the Meat Packing District (assuming a start at West 14th Street at 9th Avenue – walk to the elective shopping mall, Chelsea Market at West 15th Street (the former factory of Nabisco, the maker of the Oreo cookie) and walk through the market building to the opposite side (try to avoid eating too much on the way through). Walk out the other side and, to the right, you’ll see an elevator which will bring you up to the High Line Park. Take a bit of a walk to the north, stopping to gaze through the picture window overlooking 9th Avenue, and then continuing on between the pair of condominiums with “bowed” windows which overlook (and exposed to voyeurism from) the High Line path.

Remembering that every further step increases the distance you will have to back-track over, reverse your walking direction. Shortly you will see evidence, to the right, where a track spur entered a building. It is clear from the brickwork that the opening would accept a complete box car and, inside the building, were elevators designed to bring that car to an upper floor for loading. Continue on, under the overpass and recognizing railroad ties and rails under the wooden lounge chairs as you walk towards the Whitney Museum (which we will leave for another day).

Leave the High Line at the 14th Street staircase and cross 12th Avenue to the new “Little Island Park” which is built on mushroom-like pods on top of pilings emulating those found in the adjacent ruins of another pier. Try out the musical instruments which are scattered around and make sure to take a look at the amphitheater.

Leave the park and cross through the former Gansevoort Meat Packing District of tony shops to Hudson Street.

Walk in the downtown direction on Hudson Street and you will be entering Greenwich Village. In the “olden times” this was a cheap place to live and therefore attracted a lot of poor artistic types. It is now, like almost all of Manhattan too expensive for even most middle class to afford. Keep an eye out for 435 Hudson on your right. This is a L’Oreal Professional Academy and, depending on what they have going on, your wife may be able to score a free professional hair styling. If this is not of interest, (before reaching the above mentioned boring place), make a left turn on Morton Street. We are going to wander a bit to give you a few flavors of “The Village”. Continue on Morton (past 7th Avenue) until Bleeker Street.

Make a right turn on Bleeker Street (a commercial street with some interesting boutiques, bakeries and that sort of thing. Take Bleeker as far as MacDougal Street and you will be at the center of one of NYC’s jazz/country music spots – clubs such as the Bitter end have been there since before I was born. Make a left MacDougal and take it a few blocks to Washington Square Park (whose proximity to where my former company was located gave it its name).

This is a social center for both the denizens of the neighborhood and the students of the adjacent NYU University. Walk across the park for a special view up 5th Avenue to the Empire state Building and the Chrysler Building (my personal favorite skyscraper). Walk north on 5th Avenue on the right side of the street and about the middle of the first block you will find a small courtyard named “Washington Mews”. These were originally the stables and carriage houses for the town houses facing Washington Square Park between 5th Avenue and University Place. They are currently highly sought after faculty housing for NYU.

Make a right turn at the end of the block at East 8th Street and walk past Broadway to Lafayette Street. Before the turn of the nineteenth century, this area was a posh place to live and the Metropolitan Opera House was located around here.

To your right, across a plaza with a large black cube type sculpture, you will see a large (old) brown colored building. This is “The Cooper Union” – a free (and therefore highly competitive) college devoted to engineering, architecture and the arts endowed by Peter Cooper the initial railroad magnate of the US. It is unique in that the first elevator in the City was installed in the building. When it was built (before the elevator was “invented” – actually made practical by a safety locking system invented by Mr. Otis) a shaft was created with the expectation that one day there would be elevators. When they finally came about, the building was already waiting (though the shaft was oval, rather than rectangular – but who knew?).

Make a right turn on Lafayette Street (there is a large Starbucks coffee shop if you need a toilet). If you subsequently made a left turn on Astor Place (known as St. Marks Place) and walked straight, you would be going into the “East Village” – the center of NY’s hippy culture during the 1960’s and a couple of blocks further on you would reach “Alphabet City”, traditionally the more heavily drug oriented portion of the East Village (while it has gotten better, which is why I originally suggested a daytime visit years ago, though the area today is heavily trafficked and substantially gentrified).

Instead, we are going to make a right and head down Lafayette Street. Just past Astor Place (where I had one of my offices about a million years ago), on the right side, look for a building with a series of tall columns in front. This is one of the oldest buildings in the area and you might want to read the brass plaque attached to it. Across the street from “The Colonnade” is the NY Shakespeare Theatre which runs open air Shakespeare in Central Park during the summer. Head down Lafayette Street (enjoying the eclectic stores) to Great Jones Street and make a right turn. All through this walk, it is important to look at the architecture as it is constantly changing and some of the styles are unique to the area. Walk a block and make a left turn on Broadway. You will not be alone (and almost everyone you see for the next couple of kilometers will likely be a tourist).

When you cross the wide Houston Street (pronounced here like it is spelled, rather than the long “u” used for the similarly spelled city in Texas), you will be entering “SOHO” (South of Houston Street). Continue another block to Spring Street (location of a water pumping station owned by Arron Burr, Thomas Jefferson’s Vice President and the man who killed Alexander Hamilton simplistically the founder of the central bank of the United States in a duel. Wooden water pipes made from hollowed logs are still sometimes dug up here). Cross Broadway and walk down Prince Street, experiencing a bit of SOHO and watch for the Apple store a couple of blocks down on the right (former post office). Walk another few blocks to “West Broadway” and make a left turn.

Walk past the art galleries and assorted high end highly tourist-oriented retail areas and make a left on the next corner onto Spring Street. Look up and down the street and you will see a load of world class product logos (Chanel, Longchamp, Armani, etc.). When the famous bank robber Willie Sutton was asked why he robbed banks, he answered “because that’s where they keep the money”. These shops are here because this is where they keep the rich tourists. As you head back to Broadway, keep an eye out for number 97 Spring Street on the left (my office for 14 years when this was the cheapest neighborhood in the city). Walk back across Broadway (trying to shield the Bloomingdale’s department store sign to the right so your wife does not notice it : -) and you’ll pass a posh French bistro on the right called Balthazar (good food, high prices).

Keep walking down Spring Street back across Lafayette Street (technically leaving SOHO and entering Little Italy) and looking to your right (apparently in the middle of the street) is a domed palatial building. Until about 20 years ago (when it was moved beyond the arch of the municipal building downtown near city hall) this building was NY Police Department headquarters and is now full of very fancy condominiums.

Continue about a block further down Spring Street to number 45 – a restaurant called Taim (Hebrew for tasty). This is one of the best falafel places in the city.

While logic would dictate a walk through Little Italy at this point, the reality is that the neighborhood, like much of Brooklyn’s Bensonhurst has lost a lot of its attraction as most of the signage is in Chinese. The restaurants, as expected, are mostly highly tourist-oriented retail areas with high prices and average food. (For really good Italian food, there are plenty of places in Brooklyn and the Bronx.

For REALLY good (as well as REALLY expensive) Italian food in Manhattan, Rao’s at 455 East 114th Street (between 1st Avenue and Pleasant Avenue) in Harlem is the place to go. The bad news is a reservation is nearly impossible to get (and the meal will be expensive enough that you might as well have flown to Florence). Likewise, having seen an authentic Chinese area in Brooklyn’s Sunset Park, we are going to forgo Manhattan’s Chinatown as a cross between being touristy and redundant. Canal Street, which was at one point known for high quality knockoffs of designer stuff has pretty much been closed down by the cops except for places that I would not recommend going to (as you would be too exposed to issues).

Anyhow, apologies aside, what we are going to do is continue walking down Spring Street until the Bowery, a few blocks ahead.

The Bowery was originally the road to Peter Stuyvesant’s country farm (one of the first Dutch governors of New Amsterdam – which became New York when the British took over). For most of the 1900’s it was NYC’s main skid row with the storefronts a mixture of bars, lighting fixture distributors and used restaurant supply distributers. (That was in the days when Center Street was occupied by used machine tool dealers, Spring Street with leather wholesalers, Broadway in this area with fabric and bed clothes wholesalers and so on – many of which have now disappeared except for a handful of legacy businesses). The second floors of the Bowery buildings were flop houses where you could rent a room the size of a small bed for $.25 for the night and sleep off the booze that was progressively making you blind – all gone now and replaced by apartments for young stock brokers who are more likely to buy dinner at higher-end specialty grocery stores than in a bar.

We are going to cross the Bowery and make a left, walking as far as Houston Street (2 blocks) and make a right (stay on the same side of Houston Street). You are now entering the Lower East Side (years ago the original neighborhood of many Jewish immigrants from Europe, but that is all in the past – though some legacy restaurants live on). In a block, we pass by the end of a park and cross Forsyth Street. On your right you will be passing Yonah Schimmel’s Knish Bakery at number 137 Houston Street. A knish is a traditional eastern European “thing” made from potato, kasha, cheese, spinach, cherries or whatever. They were fairly common at one point, but this is one of the last places which make decent ones. (Warning – they are filling and we are on our way to an eatery).
As we continue on, past the double conduit of Allen Street, we’ll be passing Russ & Daughters at 179 Houston. This is the type of “amateurish” Russian appetizing counters that we saw in Brighton Beach, Brooklyn brought to its multi-generational apex.

Crossing the next street (Orchard street – which at one time was known for designer bargains obtained from the garment workshops of 7th Avenue and sold for a song – but with the original labels cut out.

The garment center no longer manufactures and Orchard Street is a far less distinctive as a shopping destination than in previous decades), we head to Ludlow Street and find the famous Katz’s Delicatessen on the corner. Katz Deli is full of tourists, but about 1/3 of the people eating there are “genuine” New Yorkers (It is a place I end up at a few times a year). There are two ways to eat there – the civilized way, where you take a table and are served by a waiter – and the “fun” way where one of you claims a couple of seats at a table and the other waits on line for your choice of food. It is known for its meat sandwiches (if you are adventurous, you can try a tongue sandwich, otherwise the pastrami is about as good as it gets). Normally the bread to ask for is rye with mustard. They will give a plate of pickles (ask for “full sour” and pickled green tomatoes). They generally don’t charge locals for the pickles, but may try to charge out-of-towners.

When you enter they will give you a paper ticket on which prices are written (DO NOT LOSE THE TICKETS!). When you wait for your sandwiches, fold a dollar and hold it behind the ticket tilted so the sandwich maker will see that he’s getting a tip. The sandwiches will be larger and likely he’ll cut you a snack to eat while you are waiting. The “traditional” soda is a Dr. Brown’s “Cel-Ray” (A celery seed flavored soft drink). Sandwiches are fairly expensive (in the $23-$26 range), but the place is worth seeing. If you want to pay by credit card (and beat the line at the cash register), go to the rear of the restaurant where they have a “take-away” counter. They have a credit card machine, but there is not one at the cash register near the front of the restaurant. Just show the credit card receipt on the way out and avoid the long line.

After grazing at the restaurant, make a right turn on Ludlow Street and look at some interesting small shops (particularly lively during daylight and evening hours). We are going to walk two blocks to Rivington Street and turn left, stopping at Economy Candy (110 Rivington), to see one of the world’s broadest display of international and legacy candies for sale (at generally very reasonable prices). This is where my wife picks up her favorite Hopjes Dutch coffee candies if we haven’t restocked in Holland for a while.

Make a right turn at the corner of Essex Street and when you reach Delancey Street in a block, ;ook for the subway station which mentions the “J”, “Z” and “M” lines (do not get on the “F” train by mistake). Take either the “J”, “Z” or “M” (does not matter which of these) one stop to Marcy Avenue and rise above the earth. Walk along Broadway in the opposite direction from the approach way to the Williamsburg Bridge. In two blocks (at 178 Broadway) you will find Peter Luger’s Steak House. Lunch of a hamburger here is much less expensive than steak for dinner.

Turn down Driggs Avenue (corner of Broadway where Peter Luger is) and walk a couple of blocks to Division Street. Make a left turn and walk the two blocks to Roebling Street. This Hasidic Jewish neighborhood remains one of NYC’s most distinctive traditional communities and is the home of the Satimar sect. (On Saturday, you can see the men in their full regalia, but the shops are all closed. The reason all of the women’s hairdo’s are all neat is that they are all wigs). If you happen to pass the deli name “Gottlieb’s” at 352 Roebling, you might peek in. While Katz’s Deli is “kosher style”, this one is a true kosher deli. While the sandwiches at Katz’s are more expensive, I think they are also better – pays yer money and takes yer choice.

On Division, between Driggs and Roebling you should find the B62 bus going in the direction of Queens Plaza (and AWAY from Fulton Mall - ask to be sure as this bus makes a few sharp turns around here). Take it along Bedford Avenue and get off (after it passes a large park) at Manhattan Avenue. You are in the Polish neighborhood of Greenpoint and while it is a few generations old, so it is not as “in your face” as Brighton Beach is with the Russians, a walk of a block down Manhattan Avenue will make it pretty obvious. OK, now cross the street back to Bedford Avenue and walk past the park. Once you come out the other end, you’ll be in the younger, hipper part of Williamsburg. As you pass N. 8th Street, look to your right and you’ll see the “Old Poland Bakery” which has a large collection of artisanal rye and multigrain breads (and a place I stock up at every time I visit). Walk along Bedford Avenue about as far at N. 1st Street to get a feel for the eclectic bunch of bars, restaurants and boutiques (this is what SoHo looked like in the 1980’s before it got posh).

Then backtrack to N. 7th Street and make a right turn to the “L” subway. Take this train towards Manhattan and get off at the last stop (5 stops, I think) at 14th Street and 8th Avenue in the Meat Packing District.
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