GPS: 44°47'N 106°57'W
Sheridan is a lot like Jackson Hole was 50 years ago: still more cow town than kitsch. While you may spot the odd rusticator at the King’s Saddlery Museum, the folks queuing up in the adjacent tack store will put ropes, saddles, and Stetsons to practical use. Sheridan’s compact downtown—a mere blip in the open grasslands beneath the Bighorn Mountains—hasn’t changed much since it was founded in 1882. Most of the brick two-stories lining Main Street are Old West originals, though these days art galleries and outfitters are likelier tenants than general stores.
Cowboy up on a day ride in Bighorn National Forest with South Fork Mountain Lodge & Outfitters (one-day guided horseback-riding trip, $150, including lunch; www.southfork-lodge.com). Farther west, the caves of Tongue River Canyon—where Crazy Horse set up his final camp—are a must for experienced spelunkers.
Wind down with a “ditch” (Plains speak for whiskey and water), and “you can’t be in Wyoming without having prime rib,” according to 65-year Sheridan resident Judy Taylor. Our pick: the rosemary-rubbed cut at 1893 Grille & Spirits, a National Historic Landmark with character to spare—Teddy Roosevelt and Ernest Hemingway were frequent guests, and onetime owner Buffalo Bill auditioned acts for his “Wild West Show” on the porch (www.1893grille.com).
Make the solar-electric rooms at Spahn’s Big Horn Mountain Bed & Breakfast your base (doubles from $115; www.bighorn-wyoming.com).