Another Round! Great Old-Fashioned Bars

This blog post was updated on January 20, 2023.

A lot of bars pride themselves on being trendy and modern. Others have been around for decades, and their history is just as impressive as their cocktail menu. If you’re looking for great travel destinations for vintage bars, here are just a few pubs, lounges, taverns, and speakeasies where you can enjoy everything from old-fashioned Hollywood glamor to mobster-era nostalgia.

Sazerac Bar — New Orleans

Sazerac and Champagne by Steve Devol licensed under CC BY-ND 2.0

You can’t talk about the best bars in America without dipping into New Orleans. Located within the Roosevelt Hotel, the Sazerac is named for the official cocktail of the Big Easy, and its extensive drink menu includes many other classic and modern spirits. Whether you’re in the mood for a Harvey Wallbanger or a Duckhorn Chardonnay, you can find it here. As you sip, you can also take in the low lights and richly padded banquettes framing the curved, wood-paneled walls. Everything says “luxury,” which is also another way of saying “New Orleans.”

The Musso & Frank Grill — Los Angeles

Hollywood: Musso & Frank Grille by Chris Bertram licensed under CC BY-ND 2.0

A hot spot during Hollywood’s Golden Age, the Musso & Frank Grill dates back to 1919, but its most famous patrons have ranged from silent film stars of the ’20s (Charlie Chaplin, anyone?) to cultural icons of the ’60s (man’s man Steve McQueen). Its décor is brimming with the essence of old Hollywood, including mahogany tables, red leather booths, and a waitstaff in formal jackets and ties. While it used to be little more than a bar, Musso & Frank has evolved into a fine dining establishment with an impressive gourmet menu, so don’t be afraid to order some bouillabaisse with your bourbon. And don’t be afraid to ask about sitting at Humphrey Bogart’s favorite spot at the counter, either!

Green Mill Cocktail Lounge — Chicago

Green Mill Cocktail Lounge by Kenneth C. Zirkel licensed under CC BY-ND 2.0

The Green Mill Cocktail Lounge was once owned by a lieutenant of Al Capone during the Prohibition era. In fact, there are still rum-running tunnels beneath the building to this day! The action remains above ground, however, with all of the swanky and stylish décor that you’d expect from a former speakeasy. There are neon lights, framed photos of mobsters, and ornate, half-naked statues dating back to the Jazz Age. There’s even a baby grand tucked by a stage where you can enjoy live music on the weekends. When you’re in the mood to drink like it’s a crime, consider swinging by the Green Mill Cocktail Lounge.

King Cole Bar — New York City

St. Regis Bar – Manhattan – Maxfield Parrish Mural – Old King Cole by Alan English CPA licensed under CC BY-ND 2.0

Located within the historic St. Regis Hotel, the King Cole Bar is a throwback to another era. It’s easy to imagine the likes of Marilyn Monroe and John Lennon swanning about its white tablecloths and glittering chandeliers, and that’s exactly what they used to do. Some people even credit the King Cole Bar with being the birthplace of the Bloody Mary. Even if you dispute their claim, however, it’s a nice bar with a lot to offer in terms of vintage allure. Just make sure that your wallet is ready. As a luxury hotel located on Manhattan’s Fifth Avenue, the St. Regis has prices that reflect the prestige.

Round Robin Bar — Washington DC

Washington DC – Willard InterContinental Hotel by Bill Badzo licensed under CC BY-ND 2.0

If you’re a fan of mint juleps, the perennial southern classic, you might want to duck into the Round Robin Bar in Washington, DC. This is where that iconic libation was first introduced to northern folk, by way of a Kentucky senator. As expected of a bar in America’s most political city, the Round Robin boasts patrons who are mostly the upper echelons of society, so much so that the establishment has been nicknamed “The Oval Office of Bars.”

You don’t need a pedigree to visit the Round Robin, however. The bar is located within the Willard InterContinental Hotel and open to everyone, so you can stroll right in and enjoy its old-money, leather-and-mahogany vibe. You don’t even need to be a guest at the hotel. If you have a thirst, you can come and quench it with the juleps.

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Green Dragon Tavern — Boston

Green Dragon Tavern by Steve Petrucelli licensed under CC BY-ND 2.0

When it’s time to settle your tab, how about signing your John Hancock somewhere that John Hancock actually liked to drink? The Green Dragon Tavern dates all of the way back to 1654, and it’s played host to numerous New Englanders, including Mr. Hancock and the legendary Paul Revere. Rumor has it that Revere actually started his famed midnight ride from the Green Dragon after overhearing the plans of the British over a tankard! While today’s version of the bar is a lot different from its 17th century counterpart, it still has history deeply embedded in its walls, and this is apparent everywhere from its menu to its interior design. Consider a visit if you’re in Boston and interested in drinking in some American history — quite literally.

Do you have a favorite old-time watering hole? Let us know in the comments below!