This classic western town—it was a stop on the Oregon Trail—is known for the famous Pendleton Round-up, which takes place each September. But its Western charms are available year-round, including on July 15, which brings the Whisky Music Festival (1205 SW Court Ave.) to town. This year’s fest features Maroon 5, plus food trucks, wine and beer (and, of course, Pendleton whisky).

Soak up the Western Vibe: Step into the Old (and new) West at Hamley & Co. (30 SE Court Ave.; 541.278.1100). The Hamley family has been making leather saddles since 1883, and this shop has roots that date to 1905. Along with saddles, you’ll find other artisan-made leather goods, such as purses and belts (and buckles), as well as bronze artwork and jewelry. At the related but much newer Hamley Steakhouse (8 SE Court Ave.; 541.278.1100), the meticulously cultivated Western-style interior includes 18th-century bars, a tin ceiling, and plenty of woodwork and Old West artifacts. Afterward, enjoy the live entertainment—and impressive selection of beers on tap—at Cadillac Jack’s Saloon & Grill (1703 SW Emigrant Ave.; 541.276.9422).

Go Underground: Learn about the town’s racy past on an excursion guided by Pendleton Underground Tours (31 SW Emigrant Ave.; 541.276.0730), where subjects include the town’s history of illegal gambling and prostitution, along with less salacious details, such as how Chinese immigrants helped build the West. For a more elevated experience, view an exhibit at the Pendleton Center for the Arts (free admission; 214 N Main St.; 541.278.9201); in July, contemporary art from Portland’s PDX gallery will be featured. Visit the Pendleton Mill Store and reserve a space on a tour of the famous wool mill to learn about its century-old weaving process (1307 SE Court Place; 541.276.6911). Afterward, buy a woven wool blanket perfect for summer camping.

Say Good Night: At the Pendleton House Historic Inn (Pendleton, 311 N Main St.; 541.276.8581), a 1917 Italianate-style mansion, you can bed down in one of six charming rooms. If you travel with your horse, reserve a spot at Neigh-bors Horse Motel and Bed & Breakfast (543 NW 21st St.; 541.276.6737; ), where the kitchen will be stocked with breakfast fixings and the barn will accommodate your four-footed friend. Without a horse, but a fan of them? You can still stay here and enjoy the horses on the bucolic property.