The reason behind the quirky name of Sisters, Oregon, becomes evident as soon as you arrive in the Deschutes County town. A trio of volcanic mountains — Faith (North Sister), Hope (Middle Sister) and Charity (South Sister) — provide a knockout backdrop for this little spot in central Oregon.

Sometimes referred to as the “Gateway to the Cascades,” Sisters was established in 1901 and grew into a prosperous lumber town. But, by the 1960s, the logging industry was winding down and Sisters turned its eye to travel and tourism instead, promoting the region’s laid-back lifestyle and abundant natural gifts. With easy access to the 1.6-million acre Deschutes National Forest, as well as eclectic dining and shopping in town, a long weekend in Sisters gallops by.

Here’s a sample itinerary for three days’ worth of Cascades fun in charming Sisters.

Sisters is a town of about 3,000 residents, but there are a surprising amount of lodgings for a place of its size. The FivePine Lodge and Spa comes highly recommended, with thousands of rave reviews across the web and an overall rating hovering around five stars on the biggest aggregation sites. It’s location sits at the edge of the national forest but just a few minutes’ walk from town. There’s a free beer and wine hour each night in the lobby, where you can meet other FivePine guests and trade tall tales about your adventures in the forest.

FivePine offers 32 romantically “rustic” guest rooms. You can either stay in the lodge building, which has a welcoming stone hearth in the lobby, or in the modern cabins on the grounds. All rooms have fireplaces, soaking tubs and cozy sitting areas. For families traveling with kids in Sisters, the 740-square-foot Caboose Cabin features extra space and two spacious beds: a king in the main room and a queen tucked away in an alcove.

Another top-rated choice is the Left Coast Lodge, a motel on the other side of town with rooms that feel more like cozy Airbnb rentals in the woods than uninspired hotel digs. Left Coast Lodge is ideal for travelers with pets, as all rooms are pet-friendly and the grounds include a private dog park. Every room also comes with an air purifier. You might find the rooms are surprisingly cheap for all you get.

After checking in at your lodgings, take the short walk or drive into downtown Sisters to check out the local shops and restaurants. Inside Kalamazoo’s Antique Mall, a collection of vendors sell their wares, which range from used books and housewares to outsider art and old campaign buttons. Gather your vintage goodies and walk down the street to join what may be a line out the door at Sisters Bakery for a sweet snack.

For such a small town, Sisters is home to a sizeable community of artists. As you stroll around town, you’ll notice public art at every turn. Artistic works, in the form of murals, sculptures, mosaics and even a fire pit, provide insight into the local vibe and culture. In particular, look for the installations in Fir Street Park and Barclay Park.

Once you’ve checked out some of the public artwork and finished your baked goods, take time to visit Dixie’s, a shop selling Western wear for men, women and children, has a great selection of hats — felt, straw, knit and even trucker caps — and Pendleton blankets. Beware: After browsing Dixie’s, you may feel compelled to make a few mountain-cowboy-chic tweaks to your closet.

If you’re up for a challenge and want to hit the woods, Peterson Ridge Trail is great for a day of hiking or biking. (You can rent a mountain bike in town at Eurosports, a four-minute ride away from the trailhead.) The well maintained, 14.8-mile loop has an elevation gain of 800 feet and takes about five hours to hike. Since it runs along on the ridge, you’ll enjoy great mountain views but no shade. Remember sun protection and bring lots of water. 

Come dinnertime, try the Open Door, a local wine bar that plays double duty as an art gallery. Panels of stained glass and museum-lit paintings enliven the cozy log cabin atmosphere. Daily specials on the menu reflect seasonal ingredients and usually include a flatbread, a pasta option, a special lasagna, a soup and a fish entree. Just know that, even in high season, most restaurants in Sisters close very early. Check the hours and make dinner reservations, even at the most casual spots.

If you’re staying at FivePine Lodge, you can enjoy a complimentary continental breakfast, but a solid alternative is the Sisters Coffee Co. flagship shop, located in a historic wooden building with a floor-to-double-height-ceiling river stone fireplace. Order one of the breakfast sandwiches served on an English muffin and, obviously, don’t miss the coffee. The brand has been roasting and brewing in Sisters for over 20 years and have expanded to shops in Bend and Portland, too. Grab an extra pastry to go so you’ll have something to snack on while you’re on the trail — because we’re going hiking. 

For a moderate hike, try the peaceful Whychus Creek Rim and Creek Loop, just five minutes from the coffee shop. This 4.7-mile loop has an elevation gain of 505 feet through ponderosa pine trees and juniper undergrowth, and runs along the edge of a river gorge. Photographers will love that, from April through July, this trail also sees you traipsing past an abundance of wildflowers.

Regardless of if you have a room at FivePines, you’ll be glad you booked a post-hike massage at the lodge’s on-site Shibui Spa. In addition to your chosen treatment (couples massages are popular here as are hot stone treatments), the spa maintains a Swedish dry sauna and a thermal soaking pool.

To finish off your day, check what’s playing at the independent Sisters Movie House. The theater screens first-run hits as well as older films, and offers a pretty sizable selection of snacks, sandwiches and burgers. Eat in your seat while you enjoy the movie or wait for an after-show dinner at Three Creeks Brewing next door — provided your movie ends before it closes at 8 p.m. This brewery, popular with the locals, pours not just its own craft beers but has a serious cocktail menu and reliable pub fare.

By this point, you will likely be looking to get a little farther out of town and that’s when you should make the 40-minute drive to spectacular Smith Rock State Park. With trails both tough (like the aptly named Misery Ridge Trail) and easy (the much more forgiving Wolf Tree Trail), there’s an option for whatever you’re feeling. The park’s dramatic landscape, created by volcanic activity over 30 million years ago, makes it a top destination for rock climbing enthusiasts, too.

A stop at Oliver Lemon’s market in Terrebonne, OR (the town right outside the park) can set you up with hiking snacks or some provisions for a trailside picnic.  

If you are an experienced cyclist, the Sisters to Smith Rock Scenic Bikeway offers a breathtaking 36-mile ride that replaces the drive to the park. Official route signs, maintained by Oregon’s parks and recreation department, are up all along the route.

This story was edited by Hearst Newspapers Managing Editor Kristina Moy; you can contact her at [email protected].