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Midnight In NYC: A Trip Back to the 1920s

Experience the glitz, glamour, and grit of 1920s New York at these nostalgic destinations.

If you’re craving a healthy dose of nostalgia, Manhattan does not disappoint. The city’s storied history lives on through period vintage shops, charming saloons, and “vintage” transportation.

Step back in time and experience the mystique of old New York firsthand at these 1920s-themed destinations.

1. Landmark Vintage Bicycles

This East Village shop offers over 100 vintage and new bikes to choose from (or simply admire), plus a repair shop and plenty of biking accessories. Rent a charming vintage Schwinn to ride around town during the crisp autumn months.

Landmark Vintage Bicycles is located at 43 Avenue A.

2. Blacktail

Though it was recently voted Best New American Bar of 2017, downtown watering hole Blacktail is firmly and passionately rooted in the past. Inspired by stories of bartenders leaving America during Prohibition and boarding some of the first commercial flights in history to escape to places like Cuba, this bar takes its name from a fleet of black-painted planes that regularly carried expats to Havana. Blacktail offers a wide selection of top-notch Cuban cocktails and food, including contemporary interpretations of mixed drinks from the 1920s through the 1950s.

Blacktail is located at 22 Battery Place on the 2nd floor of Pier A.

3. Manhattan Cricket Club

This club is a vintage speakeasy that takes inspiration from the old-fashioned, sophisticated gentlemen’s clubs of yore — the type of place where members can sip handcrafted cocktails and brush elbows with Manhattan’s elite. There’s an etiquette that must be followed for those who enter the club, which includes adhering to the dress code, refraining from photography and phone calls, and (of course) avoiding fisticuffs. If you’re not a member, don’t worry: walk-ins are accepted, but only for parties of six or less.

Manhattan Cricket Club is located at 226 West 79th Street.

4. New York Vintage

New York Vintage offers an elaborate and curated peek into the high-end couture of the past. Browse through 100 years of style in this one-stop shop, including classic pieces from designers like Chanel and Versace. You’ll be in good company: New York Vintage’s showroom is a popular place for costume designers and celebrity stylists to find unique items of clothing for films and red carpet awards shows.

New York Vintage is located at 117 West 25th Street.

5. P.J. Clarke’s

P.J. Clarke’s is a classic “saloon,” boasting the tagline “We were old before it was cool.” And they were: this bar and eatery has been around since 1884, and prides itself on serving the same consistent, high-quality food and drink that it’s been dishing out for the past 100-plus years. With such a long history, it’s no surprise that notable names have paid P.J. Clarke’s a visit, including Buddy Holly, who proposed to his wife there five hours after meeting her; Nat King Cole, who loved the bacon cheeseburger; and Frank Sinatra, who was known to stay until closing time.

P.J. Clarke’s is located at 915 Third Avenue.

Affinia cares about making sure you get to see as much of New York — new and vintage — as possible. That’s why we’re offering a special free nights deal: book four nights for the price of three, or three nights for the price of two.

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