Two things link cowboys, beat poets, and rock stars: a propensity for living it up, and an affinity for the Mile High City. And there’s no better neighborhood to find the best of Denver nightlife than LoDo (Lower Downtown Denver to its grandmother), the city’s oldest neighborhood and the current home of a host of nightclubs, music venues, restaurants, and boutiques. In just one night, revelers can walk in the steps of the gold-mining settlers, visit a local brewery in the shadow of the city’s first train station, and catch modern poets carrying on Jack Kerouac’s legacy.

Burgers with the Beats

Any student of frontier poetry—or American history—would be remiss to pass up a visit to My Brother’s Bar, an oasis of old-fashioned eats and ice-cold beer virtually unchanged since it was the favored watering hole of Jack Kerouac, Neal Cassady, and Allen Ginsberg. If you happen to make a call from the pay phone in back, keep your eyes peeled for a framed letter from Cassady himself, asking a friend to settle a bill at the bar while the poet was holed up in the Colorado Reformatory. There’s no sign for this historic hideaway, but it’s worth the extra time to find it, even if it’s just for the jalapeño cream-cheese burger.

Subterranean Salaciousness

The D&F Clocktower might be 20 floors tall, but some of the best sights it offers are underground at Lannie’s Clocktower Cabaret. From circus sideshows to bawdy burlesque performances, the basement-level venue provides a freewheeling glimpse of Wild West entertainment with a modern edge. Presiding over it all is Lannie herself and co-owner Jefferson “Naughty Pierre” Arca, splitting MC duties with aplomb and an R-rated sense of humor. Besides their regular titillation fests, the stage hosts some of the nation’s best-beloved standup comedians, with past stars including Roseanne Barr, Leslie Jordan, and Will Durst.

Major Fun in a (Former) Miner Neighborhood

The oldest block in the oldest neighborhood, Larimer Square bears the name of Denver’s founder, General William Larimer, who moved west in the wake of the Gold Rush. But much has changed since 1858. Once the home of Denver’s first bank, bookstore, post office, and theater, the area remains a major hub of things to do in Denver thanks to an abundance of fashionable boutiques, gourmet restaurants, and swanky nightclubs and bars. Along the stretch of Larimer Street between 14th and 15th, good-time-seekers can stumble on a classic Irish pub in Maloney’s Tavern, an immaculately curated wine and tapas bar in Cru Wine Bar, and a chef-driven gourmet cocktail lounge in Green Russell.