When it comes to history, there is no single building more important to Aspen’s narrative than the Hotel Jerome. Originally built in 1889 by town founding father Jerome B. Wheeler, the hotel has stood on Main Street since the Silver Rush. Tucked inside sits the J Bar (330 E. Main St., 970-429-7674, hoteljerome.aubergeresorts.com/dining) with its tin ceilings, elaborately carved back bar (ask to see “the drawer”), and ever-growing roster of actors, writers, and other celebrities who have bellied up. True history buffs will want to sip an Aspen Crud, the whiskey-spiked milkshake that used to satiate thirsty miners and has been on the menu since the 1920s. Add in an order of potato chip–crusted fried pickles with horseradish dipping sauce for snacking or a hefty burger.

Two blocks up, Wheeler’s influence spins ever farther, thanks to the grand Wheeler Opera House he built, also in 1889. The building’s southeast flank not only offers one of the best unobstructed views of Aspen Mountain, but the ground level is also home to the brand-new Aspen Public House (328 E. Hyman Ave., 970-710-7026, publichouseaspen.com). The gastropub, which opened in June, serves breakfast, lunch (order the porchetta poutine and charred Caesar), and dinner and pays homage to its historic setting with renovated but timeless interiors.

Walk another block up to Cooper Avenue on the pedestrian mall and find yourself at the Red Onion (420 E. Cooper Ave., 970-925-9955, redonionaspen.com). Tom Latta’s New Brick Saloon was built in 1892 and gained its nickname, the “Red Onion,” on opening night. Depending on whom you ask, the moniker either refers to something rare and unexpected or a hole in the wall. Either way, the name became official in 1947 after Johnny Litchfield, a member of the 10th Mountain Division, bought the space and remodeled it. Through the years, the Onion has been reworked and expanded (which means more walls for historic photos), but the bar itself is exactly as it was in 1892. It’s still a place for tossing down a pint and a burger. Don’t miss the new outdoor patio along the pedestrian mall—just look for the Onion’s iconic red awnings.