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Stay: Go with someplace central like the Allegro Royal Sonesta and catch a cab down to Jeffery Pub for your evening fun.
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It’s a bit of a trek from the city center, but well-worth it. In fact, it’s one of the nation’s oldest operating Black-owned gay bars. Most visitors are familiar with Chicago’s Boystown (now North Halsted) neighborhood, but this bar on Chicago’s Southside has been quietly catering to a largely gay and Black clientele since the 1960s. Stay: Thanks to its central location, The Courtyard by Marriott Oakland Downtown offers a solid base for exploring Oakland. Both opened in 1933, though rumor has it that White Horse Inn continued to operate as an off-the-radar speakeasy during Prohibition. This Oakland spot claims to be the oldest running gay bar in the U.S., rivaling New Orleans’ Café Lafitte in Exile. Stay: Hotel Max offers contemporary comfort not far from Wildrose, but also close to major Seattle attractions like Pike Place Market. Open since 1984, the Wildrose in Seattle is the West Coast’s longest running lesbian bar, and one of maybe a dozen remaining lesbian taprooms in the country.
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Stay: The Sheraton Four Points isn’t too far from the Raven and offers the cozy vibe you want in chilly Alaska. Pride parades in the early 1980s had attendees numbering in the teens in Anchorage, so having a bar was big news. It’s not quite as long in the tooth as some others on this list, but for conservative Alaska, it’s something to celebrate. This nightlife stalwart has been an Anchorage hangout since 1982. Stay: Nearby Dubbel Dutch offers a truly unique experience in a renovated 19 th-century house. Drag Race star Trixie Mattel is now co-owner, helping to keep the iconic venue thriving. In business since 1968, this Milwaukee bar is the longest operating gay bar in the whole of Wisconsin.
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RELATED: Join Orbitz Rewards and start earning perks today-it’s free to join! 6. Stay: Crowne Plaza Englewood is a short drive from Club Feathers for those who want to make the pilgrimage, and it’s a good stopover on the way to nearby New York City! The bar, which caters largely to a younger crowd who doesn’t have the means to make it to Manhattan, almost went under during the pandemic but luckily managed to survive. Located in River Edge, (about 30 mins from Manhattan), this is the Garden State’s oldest nightclub, serving the community for more than four decades. Stay: Hyatt Place West Palm Beach isn’t far from the action-or the water-making it a solid choice. It earned a historic designation in 2021 to help it rebuild after a devastating fire, keeping the Sunshine State institution alive. This spot in West Palm Beach is Florida’s oldest gay bar. Stay: Check into nearby Fairfield Inn by Marriott it’s close to Woody’s, another favorite gay bar in Philadelphia. It’s more upscale than gay bars are today, but it has been delivering brotherly love for decades to fans of piano bars and good cocktails. In Philly, you’ll find this space that’s loaded with LGBTQ history, despite changing names since opening in the 1920s.