A Prohibition Bar Crawl Through NYC

I love the 1920s — a lot. Midnight in Paris is one of my favorite movies. I had a Prohibition-era-themed birthday party for three years in a row. I own vintage clothes. I listen to a lot of jazz. I swing dance. If I could live in any other time, I would pick 1920s NYC or Paris. The Jazz Age and I are besties.

And that’s one of the reasons I love NYC so much: there are a lot of other people here who love that period. There are events like the massive Jazz Age Lawn Party, as well as swing dance clubs, Facebook groups, and lots and lots of Prohibition-style bars serving classic drinks while pumping out live jazz and swing music.

While the fancy cocktails they serve are not cheap (around $18 USD), I’m hooked on the atmosphere. Stepping into these bars with the music playing, people dancing, and everyone dressed the part transports me back in time to an era when things were classy, carefree, and fun. (Note: There’s some great cocktail books that can teach you how to make these in your house too!)

And, while you can find a million lists online of all the speakeasies in NYC, today I want to give you my perfect Prohibition bar-crawl itinerary so you can channel your inner Fitzgerald or Louis Long, drown in delicious drinks, and Charleston the night away.

The Dead Rabbit

Start at this bar in lower Manhattan, and make sure you go to the upstairs parlor. While it’s not a traditional speakeasy (more an old-time pub), the bartenders make excellent, excellent 19th-century-style drinks, focusing heavily on dark liquors. They offer a $1 oyster happy hour too. The dark wood paneling and classically dressed staff provide an authentic atmosphere. The bar is based on the famous Dead Rabbit Irish street gang from the 1800s (think Gangs of New York), and the menu is served as a comic. It’s one of the best bars in the entire city.

30 Water St, +1 646-422-7906, deadrabbitnyc.com. The Taproom is open 11am-4am daily. The Parlor is open 5pm-2am (Mon-Sat), and 5pm-midnight (Sun).

Apotheke

After slurping down oysters and drinks, head to this speakeasy institution in Chinatown. Mixologists in pharmacist-style clothes create complex cocktails inspired by the apothecaries and absinthe dens of 19th-century Paris. Definitely get an absinthe drink here (yes, it’s legal). Keep in mind that the dress code is strict, so dress nice.

9 Doyers St, +1 212-406-0400, apothekenyc.com. Open 6:30pm-2am (Mon-Sat), and 8pm-2am (Sun).

Fig. 19

This secret art gallery entry reveals a cozy, chandelier-lit hideaway with beautifully exposed brick walls and a dimly lit interior. The place borrows from the speakeasy theme and is one of the more upscale, sophisticated cocktail bars in town. There’s almost always has a wait, and they definitely enforce a dress code.

131 Chrystie St, figurenineteen.com. Open 6pm-2am (Tues-Wed, Sun) and 8pm-4am (Thurs-Sat). Closed Mondays.

Attaboy

This is more a speakeasy-themed lounge than somewhere that makes you feel like you’ve stepped back into the 1920s, but the creative cocktails are supreme (be sure to get an Old Fashioned). It’s also a great place to go if Fig. 19 is full, as it’s close by! (And on the way to our next stop!)

134 Eldridge St, attaboy.us/nyc. Open 6pm-4am daily.

Raines Law Room
In 1896, the New York State legislature passed the Raines Law, which prohibited the sale of alcohol on Sunday except in hotels. Hotels were allowed to serve liquor during a meal or in the guest rooms. So bars put up curtains to create “rooms,” had a sandwich that was passed around during “lunch,” and became hotels overnight. Now the law is immortalized in the ever-popular Raines Law Room. Here you arrive at an unmarked black door and ring a bell. Someone asks, “How big is your party?” and you’re told to wait before you enter the swanky hotel-style lounge, where you ring a bell on the wall every time you need a drink. If they’re full, they’ll let you wait at the bar until a seat’s available.

48 W. 17th St., raineslawroom.com. Open 5pm-2am (Mon-Thurs), 5pm-3am (Fri-Sat), and 5pm-1am (Sun).

The Back Room

Located in the Lower East Side, this bar is my happy place, my favorite speakeasy/swing bar in New York. After walking down an unmarked alley, you enter a huge room with vintage art, furniture, and chandeliers. Jazz music plays most days of the week, and on Mondays, you’ll find people swing dancing the night away. Moreover, the bar serves drinks from teacups (they did this in the ’20s to hide the fact that they were drinking), and there is a secret room behind the bookcase. Try the Chippy Collins — the best drink they make!

102 Norfolk St, +1 212-228-5098, backroomnyc.com. Open 7:30pm-3am (Mon-Thurs, Sun), and 7:30am-4am (Fri-Sat).

Death and Company

My other favorite bar in town (introduced to me by Pauline Frommer), this speakeasy has a dark, Addams Family feel to it, with its dimly lit, dark-wood space. With a rotating list of cocktails, you never know what you’ll find, but I highly suggest you get the martini (gin, straight, with a lemon twist). It’s smooth like water. I’ve yet to find a better martini in my travels (and I drink a lot of martinis!). The Old Fashioned is also really good.

433 E. Sixth St., +1 212-388-0882, deathandcompany.com. Open 6pm-2am (Sun-Thurs), and 6pm-3am (Fri-Sat).

Little Branch
Heading into the West Village, you’re probably feeling all those strong drinks by now, which is fine, because you’ll sober up as you wait in line for this place. Seating only 12 and taking no reservations, there can be a long wait here, but once inside, you’re treated to live jazz music, an intimate setting, and creative and classic cocktails. Cash only.

22 Seventh Ave. S, +1 212-929-4360. Open 7pm-2:30am (Sun-Tues) and 7pm-3am (Wed-Sat).

Bathtub Gin

Heading up to Chelsea, we finish the night at the aptly named Bathtub Gin, where you can actually sit in a vintage-style bathtub! The owners place a lot of emphasis on authenticity, and you can see it in the décor and the staff’s attire. This hip speakeasy is one of the more lively ones on the list, as it has ample space, dancing, and live music, which is why we end the night here. They also serve delicious (but pricey) food.

132 Ninth Ave, +1 646-559-1671, bathtubginnyc.com. Open 5pm-2am (Sun-Thurs), 5pm-4am (Fri), and 4pm-4am (Sat).

Honorary mentions for other great Prohibition-style bars go to:

• Dutch Kills
• The Richardson
• Angel Share
• Dear Irving

What about….?
Some of you might be wondering why I didn’t include the famous PDT (Please Don’t Tell). Because I think it’s overrated. Sure, the drinks are good, but so are drinks everywhere else. PDT is cool because you have to pick up a secret phone in a hot dog shop to get in, but once inside, the atmosphere and drinks aren’t anything really special.

Remember the following:

1. Dress nicely: These places have semi-strict dress codes, so guys should go with pants, dress shoes, and a nice shirt. Some places won’t accept you if you’re wearing sneakers.
2. Be prepared to wait: All these places are small and don’t take reservations.
3. Don’t attempt this on a weekend — the crowds get too big!
4. Go with a small group: If you come with a big group, you reduce the chance you’ll get a table.

So, there you have it. My Prohibition bar crawl through NYC takes you to the best speakeasies in the city that are synonymous with the Jazz Age. You’ll cover a lot of ground, so to make it to the end, try to limit yourself to one drink per place. You can mix and match as much as possible, tthough. Also, be sure to hydrate a lot!