Cocktails with a View: 4 Best Rooftop Bars in the U.S.

Summer is upon us. That means it’s time for flip-flops, road trips, and rooftop bar hopping. Is there anything better than sipping a well-made Old Fashioned while watching the sun set over the city skyline from 20 stories up? With that in mind, here are the best rooftop bars in the U.S.

Top of the Gate at The Watergate Hotel

Washington, D.C.

The competition among D.C.’s cocktail scene is fierce. So, when a noteworthy bar pops up that everyone seems to be talking about, it’s hard not to notice. After a $200-million renovation of the iconic Watergate Hotel, Top of the Gate emerged as one of the city’s freshest and swankiest rooftop bars. The outdoor lounge boasts panoramic views of the city skyline and the Potomac River — both best viewed at sunset. Almost as good: the 70s-inspired whiskey lounge downstairs with a 2,500-bottle-deep selection.

The Rooftop Lookout at The Envoy Hotel

Boston, Massachusetts

There’s no shortage of rooftop bars in downtown Boston. But, for our money, just one rises above the rest (get it?): The Rooftop Lookout at The Envoy Hotel. The atmosphere is everything you’d want in a picture-perfect rooftop bar: chic, but not stuffy; sophisticated, though unpretentious. Thanks to the bar’s location along Boston Harbor, the views are arguably the best of any restaurant in the city. Be warned though: you can expect a wait to get in almost any night of the week and, like the hotel it’s attached to, nothing here is cheap. Reservations are encouraged.

The Nest at Thompson Seattle

Seattle, Washington

Few brands nail the posh, swanky vibe like Thompson Hotels. So, it’s no surprise that Thompson Seattle is home to one of the city’s newest and chicest rooftop bars. The Nest ticks all the must-have boxes for a well-done rooftop bar: comfortable couches, fire pits, and lush greenery. The cocktails here are all named after birds from around the world. Most notable: the simply-named Eagle (with a coffee-infused bourbon base) and the Juniper Titmouse (Beefeater and Sichuan pepper-infused Dolin Blanc). The menu of small plates is just as inspired. Think gourmet charcuterie boards, confit boar ribs, and salmon collar with Korean wing sauce. Oh, and the views of the Seattle skyline — including Pike Place Market, Elliott Bay, and the Olympic Mountain Range — aren’t too shabby either.

Boleo at Kimpton Gray Hotel

Chicago, Illinois

Drumbar is the obvious choice. But, why not try a little something different? Perched on the 15th floor of Kimpton Gray Hotel, Boleo brings a legit taste of South America to Chicago. The retractable roof and rows of lush palms put you squarely in downtown Buenos Aires. The vibe is lively and sophisticated with plenty of well-dressed guests coming for the creative beverages and Latin-inspired fare. South American staples like Fernet and Coke and Pisco-based cocktails are on offer. But, acclaimed bartender Jess Lambert knows how to craft an inspired cocktail, so sometimes it’s best to order off-menu. For snacks, expect anticuchos, empanadas, and croquettes — all with a healthy dose of Japanese, Spanish, and Chinese influences.

For a more global view, explore the best rooftop bars in the world.


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