22 Things to Do in New York City to Experience “Old School” NYC

By | Digital Editor
Last Updated: August 31, 2023
View of classic and old school New York city and the best things to do

The Best Things to Do in New York City: Museums, Jazz Clubs, Classic Dining Establishments & Retro Bars

New Yorkers are a funny bunch. In addition to being aggressively opinionated, we’re always lamenting the “real” New York of bygone times. Current-day New Yorkers talk wistfully for the 1990s, and in the 1990s, we did the same for the 1970s, and so forth – you get the idea. And while most admit that progress is probably a good thing, we can’t help but miss the grittier days that we feel made us what we are. 

The one truism is that the only constant is change and nowhere exemplifies that more than New York City. Restaurants come and go with disturbing speed, and neighborhoods quickly turn unrecognizable to those who have moved away. Perhaps this is why New Yorkers cling to establishments that so sincerely remind us of days of yore.

In this travel guide focusing on “Old” New York City, we’ll check out some establishments that have managed to either survive for unnervingly long or that manage to capture the spirit of a different time. Some are well-known and others are not, but all are throwbacks to previous decades. (Please note that all locations are in Manhattan unless otherwise stated.)

Old School Things to Do in NYC

Tenement Museum

103 Orchard St 10002

(877) 975-3786

The Lower East Side of Manhattan is where immigration exploded in the late 1800s and into the early 1900s. In particular, immigrants from southern and eastern Europe crammed into tiny tenement apartments as they scratched out meager existences in the city. At the Tenement Museum, apartments have been restored to resemble what they would have looked like back in the day. Tours offered are updated regularly and focus on either a specific family, a typical day during different years, or social movements that sprang up from the tough living conditions in the neighborhood. It’s an incredible peek into the lives of the families who worked and built New York to be what it is today.

RECOMMENDED: Take a Guided & Private Lower East Side Food and Neighborhood Tour

Museum at Eldridge Street

12 Eldridge St, New York, NY 10002

(212) 219-0302

Housed in a beautifully restored synagogue built-in 1887, the Museum at Eldridge Street was the center of life for many newly arrived Eastern European Jews at the turn of the last century and beyond. It was where newcomers could connect with family members already living in the city, meet friends from the old country, and navigate this strange new land. The architecture alone is stunning, and its place in Jewish life as New York exploded cannot be understated.

RECOMMENDED: Get Access to 13 NYC Museums & Attractions with the Borough Pass

The Apollo Theater

253 W 125th St, New York, NY 10027

(212) 531-5300

It’s impossible to stress just how important the Apollo is to American culture – countless icons have performed here, and an equally stunning number got their start here. Opened in 1913, the Apollo has been the epicenter of music, comedy, dance, and more over the last century and is a truly iconic place, both physically and in the cultural psyche of New Yorkers. Get a behind-the-scenes tour to learn all about it multi-layered history and to form a deeper appreciation for the Apollo and all that it represents.

WHERE TO STAY: Book One of These Top Hotels Near the Apollo Theater on Booking.com

Russian & Turkish Baths

268 E 10th St, New York, NY 10009

(212) 674-9250

Located just a bit north in the East Village, the 1892-built Russian & Turkish baths are a throwback to the good old-fashioned Schvitzes. Come and sweat out the grit of the city while catching up on neighborhood gossip. Pay attention to the calendar because certain hours are women-only or men-only. This is definitely not an experience for the modest!

Historic Jazz Clubs

Smalls Jazz Club

183 W 10th St, New York, NY 10014

Have you ever wished you could have experienced Charlie Parker in a tiny club back in the day? While the uptown clubs of the Harlem Renaissance are long gone, Small’s is alive and managing to hang on. While other historic clubs weren’t able to weather covid, Small’s somehow has and it captures the tiny, packed, basement club vibe completely. It’s hard not to be taken back to jazz’s heyday here. 

Nuyorican Poets Café

236 E 3rd St, New York, NY 10009

(212) 780-9386

As faces of immigration changed, so did the neighborhoods of New York. By the mid-1900s, the Lower East Side and East Village became increasingly more diverse as more people of Afro-Latino descent began to move in. By the 1970s, the Nuyorican Poets Café was born and quickly became an intellectual and artistic meeting place. It’s still home to some of the more creative and inventive performances, featuring everything from poetry slams and spoken word to jazz and live drumming. Keep in mind that the name of the café is a nod to the Spanish-English culture and linguistic blend that developed in the community, so performances are not always in English.

Significant Neighborhoods


Ok, now, we admit that Chinatown is mostly a tourist spot, but it’s crucial to the development of New York. Chinese immigrants have been in New York as long as Europeans but began arriving en masse in the 1870s to escape persecution in the bigoted American West. Manhattan’s Chinatown has been one of the few neighborhoods that has not demographically changed all that much. If anything, it’s expanded! Get off Canal and explore some of the smaller streets, and if you’re lucky enough to be there on market day, you’ll feel like you’ve been transported to the other side of the world.


The importance of Harlem cannot be emphasized enough. By the 1920s, it was home to the intellectual explosion that came to be known as the Harlem Renaissance and Harlem saw a proliferation of musicians, singers, dancers, poets, novelists, actors, and designers. The Apollo Theater, the Savoy, and the Cotton Club are just some of the famous performance spaces that thrived. Do yourself a favor and take a walking tour of the neighborhood to fully appreciate the architecture and the homes of the enormous talent that poured out of Harlem and influenced American art and culture up to today.

Grand Central Terminal

Grand Central is easy enough to find because a) it’s huge, and b) it’s the nexus of train and subway lines. It’s an architectural gem, from the gorgeous starry ceiling to little pockets like the Whispering Corners. Head to the Grand Central Oyster Bar for cocktails and some amazing people watching.

Coney Island Circus Sideshow

1208 Surf Ave, Brooklyn 11224

Coney Island is pretty far but it’s worth the trip. The beach itself used to be absolutely crammed on summer days as residents sought some relief from the sweltering heat, and it can still get pretty busy. But the highlights of visiting are the old-school carnival rides like the Wonder Wheel and the Coney Island Circus Sideshow. You’ll immediately be transported back to rum-running days when any odd talent would be turned into an act. Will you see a sword-swallower? An escape artist? A strongman? Who knows? But it’ll be entertaining, for sure!

Classic Eating

Katz’s Delicatessen

205 E Houston St, New York, NY 10002

(212) 254-2246

Certainly not a secret, Katz’s Delicatessen is always bustling with activity and is a wonderful throwback to the disappearing deli culture. Settle in for a legit bowl of matzo ball soup or a hot Reuben. Don’t expect warm and cuddly service, but hey – that’s part of the charm, right?

Minetta Tavern

113 MacDougal St, New York, NY 10012

(212) 475-3850

Dating back to 1937, Minetta Tavern will have you thinking you stumbled back into glorious old New York. Certainly not catering to budget-seekers, its polished brass and leather banquettes provide perfect detail for imagining a different time. If you don’t want to commit to a meal, grabbing a beer at the bar is a must.

Tasty Dumpling

42 Mulberry St, New York, NY 10013

(212) 349-0070

If you want dumplings and you want them to be tasty, this is the place. There’s something to be said for places like Tasty Dumpling that have managed to remain gloriously un-artisanal or hipster – and by consequence are actually artisanal since everything is made in-house. Cheap, filling, and delicious, you’ll want to grab a table to eat them right then and there.

Emilio’s Ballato

55 E Houston St, New York, NY 10012

(212) 274-8881

Located right on Houston Street, Emilio’s Ballato has a down-to-earth atmosphere that is a bit deceiving: the food is incredible. A targeted menu pays homage to Mama Italy, with a wine list to match. And while Italian-American restaurants certainly are not lacking in the New York metro area, Emilio’s Ballato will take you back to the early 1900s as Italian immigrants secured their place in New York history.

Caffè Reggio

119 MacDougal St, New York, NY 10012

(212) 475-9557

Caffè Reggio claims to be the home of the ‘original cappuccino’ and who are we to question? Established in 1927, Caffè Reggio has seen Greenwich Village through nearly a century of change. Settle in with a cappuccino (you sort of have to) and house-made tiramisu, and prepare for some of the best people-watching around.

Yonah Schimmel’s Knish Bakery

137 E Houston St, New York, NY 10002

(212) 477-2858

If you’ve never experienced Yonah Schimmel’s Knish Bakery… wow, are you in for it. Established in 1910, this knishery is still slinging knishes, kugels, and latkes with no signs of slowing down. You can also ship across the country. What a time to be alive.

Porto Rico Importing Co. 

201 Bleecker St, New York, NY 10012

(800) 453-5908

Not technically a place to eat, Porto Rico is still worth visiting. Established in 1907, the Bleecker Street location is home to dozens of different beans and the gorgeous scent to prove that this is one of the best coffee purveyors around. It’s pretty no-frills, with beans bulging out of huge burlap sacks everywhere. The St Mark’s Place location is a great choice for a grab-and-go cup of joe. 

Retro Drinking

The Stonewall Inn

53 Christopher St, New York, NY 10014

(212) 488-2705

Now a registered Historic Landmark, the Stonewall Inn is the location of the turning point in the fight for gay rights and equality. In 1969, sweeping arrests in the bar led to days of rioting and helped kickstart broader protests. It is, it claims, “where pride began.” (A bonus: it’s across the street from 55 Bar!)


51 E Houston St New York, NY 10012

(212) 226-8844

New Yorkers love to lament the loss of gritty dive bars and many favorites have indeed faded away. Thankfully, Milano’s does not seem to be going anywhere. Don’t expect cheerful wit and chatter – sarcasm is about all you’ll hear here. Milano’s is the perfect dose of grungier times.

King Cole Bar

Two E 55th St, New York, NY 10022

(212) 753-4500

Artist Maxfield Parrish is known for painting luminous landscapes and fanciful portraiture. Included in his works are two murals, one of which resides at the St. Regis hotel’s King Cole Bar. You’ll want snazzy attire, but the bartenders are remarkably approachable and down-to-earth. Bonus if you ask why King Cole’s attendants have the expressions they do.

The Lobby Lounge

59 W 44th St, New York, NY 10036

(212) 840-6800

The Algonquin Hotel was home to the infamous “Round Table” lunches hosted by Dorothy Parker, which were not limited to two or even three martinis. And while those days may be over for most, The Lobby Lounge gives a nice little dose of what was. Settle in with a drink and a quip for full effect. 

McSorley’s Old Ale House

15 E 7th St, New York, NY 10003

Established in the 1850s, McSorley’s is hardly a secret and as a result can be mobbed at any point in time, but it’s still worth checking out for a dose of old New York. Known for its sawdust-covered floors and for slinging two kinds of ale (light or dark), it did not allow women until the 1970s. And although it’s certainly commercialized, it will still bring you back to bars experienced by newly arrived immigrants in the 1800s – at least the male ones.

Vintage Vibe Tours

Sometimes it’s best to let the pros organize everything – so here are our favorite tours around New York that give a nod to bygone days…

Lower East Side Culture and Foods Tasting Tour is a great way to explore the LES and all that the different immigrant groups brought to the City. Learn about Little Italy, Chinatown, and more and taste incredible noshes along the way, including one of our favorites: knishes!

Greenwich Village Walking and Food Tasting Tour is another fantastic option of a historically significant neighborhood that never seems to go out of style. Learn about this dynamic area while sampling some classic NYC snacks like pizza and falafel. 

Hell’s Kitchen Food Tour & Central Park Stroll provides yet another view of New York. Hell’s Kitchen has experienced an incredible refurbishing in recent decades and is now one of the hottest spots of all sorts of culinary treats. After, relax in the vastness that is Central Park and take in all of the sights. 

Central Harlem African-American Culture Walking Tour is a must to learn all about the importance of Harlem as a cultural epicenter, both past and present. Explore significant places from the Harlem Renaissance as well as those of newcomers, like a market it Little Senegal.

Beyond Old School: Best Trending Tours & Experiences in NYC

For those of you looking to plan a quick fly through and have a perfect day in New York City, we’ve included a one day itinerary with a blend of sightseeing, shopping, and experiencing the unique vibe of the city below:

Morning: Statue of Liberty Cruise – Start your day with a 1-hour cruise around the Statue of Liberty and Ellis Island. This tour offers a close-up view of one of the world’s most famous monuments and the emblematic entrance to New York’s harbor. You’ll also journey under the Brooklyn Bridge, adding another iconic sight to your morning. The cruise departs from Battery Park, a lovely spot to enjoy a morning stroll before or after your cruise.

Late Morning: Manhattan Helicopter Tour – Next, take to the skies with a Manhattan Helicopter Tour. This narrated helicopter tour gives you a bird’s eye perspective of NYC, cruising over Manhattan’s iconic skyscrapers, coming face to face with the Statue of Liberty, and heading uptown past Central Park. This unique experience offers unparalleled views of the city and is sure to be a highlight of your day.

Afternoon: Madison Square Garden Tour – After lunch, head to Madison Square Garden for a guided arena tour. Experience this world-famous arena like never before and learn about the iconic moments that have made sports and entertainment history. Whether you’re a sports fan or not, the behind-the-scenes look at this legendary venue is fascinating.

Late Afternoon: Shopping at Woodbury Common Premium Outlets – In the late afternoon, go shopping. Enjoy discounts on designer goods from over 220 stores. This shopping haven is just an hour’s drive from Manhattan and offers a variety of high-end shops and eateries, making it a perfect spot for a shopping spree and an early dinner.

Evening: Manhattan Night Helicopter Tour – Yes, why not get on a helicopter again? End your day with a Manhattan Night Helicopter Tour. As the city lights up for the night, you’ll get a breathtaking view of the illuminated skyline. This tour offers a unique perspective of the city that never sleeps and is a perfect way to wrap up your perfect day in NYC.

Take the Trip!

And to think – we’ve barely scratched the surface here! New York is more than just Manhattan, of course, and we could write a book about all of the little gems tucked in every borough. These, though, are all within subway-able distance from each other and provide several days of New York rediscovery. Cheers!

Frequently Asked Questions about the Best Things to Do in NYC

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