Approximately half an hour from Bend or Redmond lies the town of Sisters, situated in the shadow of the Three Sisters Mountains. This area serves as a gateway to Central Oregon’s wilderness, where the Cascade Mountains transition into the high desert. With just over three thousand residents, Sisters is known for its charming bakeries, breweries and even a few bulls—one of which famously escaped from a rodeo, making national headlines. Whether you’re a full-time rancher or a weekend cowboy, a day trip to Sisters will leave you wanting to return for more.

While East Main Avenue stretches the length of town from east to west, the actual main street is West Cascade Avenue. This isn’t to say you shouldn’t explore Main Street or the other side streets that run perpendicular to it—the downtown core is only six blocks long. East Hood Avenue, which runs parallel to Cascade one block south, is also worth a visit. You'll notice that most of the vehicular and pedestrian traffic flows along Cascade Avenue. The entire community is very walkable, even in the snow (though be cautious of icy patches). Walking through Sisters feels like stepping back in time, embodying the new frontier's pioneering spirit, blending the Old West's charm with a slice of Americana and a touch of rugged Bohemian chic.

To start your day, don’t let the long line outside Sisters Bakery deter you. Instead, use that time to admire the wide range of offerings that cater to both sweet and savory cravings. While the sourdough bread flies off the shelves, you can always find at least one savory scone option that typically includes various cheeses and either bacon or chorizo. They also feature delicious Danishes, such as their recent roasted squash and goat cheese variety. For those with a sweet tooth, the bakery has an array of sugary treats, including iced oatmeal cookies, peanut butter brownies and some of the best doughnuts you’ll find anywhere. The chocolate and maple bars are impressively large, not to mention the apple fritters, which are big enough to feed a group of Pacific Crest Trail hikers on their own. If it's the season for s’mores doughnuts, that will definitely simplify your decision-making process!

Across the street is the Ski Inn Tap House and Hotel. The ground floor is spacious relative to its footprint, offering indoor and patio dining, complete with fire pits at the standing tables. The menu is concise but satisfying, featuring several burger options. If you can handle the heat, try the Jala burger, which comes with pepper jelly, jalapeño cream cheese and a bacon-wrapped popper on top of the beef patty, served on a local Big Ed's Breads bun. There are about a dozen tap handles available for drinks. The upstairs balcony is reserved for guests of the hotel’s six rooms, providing a wonderful spot to sip drinks and people-watch from more comfortable-than-they-look chairs made from old skis.

Whether you’re an actual rancher or a weekend cowboy or cowgirl, Dixie’s has you covered, literally from head to toe. From Wrangler’s denim to Scully’s embroidered Western wear, from Pendleton blankets to big, ol’ cowboy bling, down to conceal carry holsters because, don’t forget, this is Central Oregon. Dixie’s has everything from boots to belt buckles for the entire family.

Just a couple of blocks farther west, you'll find Alpaca by Design, a charming boutique specializing in alpaca wool products. Since most alpacas in the world come from Peru, much of the inventory is imported from there. However, if you've traveled to Sisters, you've likely passed at least one local alpaca farm, so you might also find some items made right here in the area. You can purchase straight yarn or "floofs" of raw alpaca wool at the store. If you need extra layers to keep warm, they offer a variety of cozy knit caps, toques, warm shawls, and super soft socks, gloves and mittens, all crafted from alpaca wool. And if that's not enough for you, you can also visit a nearby farm to pet some live alpacas!

Paulina Springs Books is also on Hood Ave. Note that Paulina is pronounced with a long “I” in these parts so that “I” doesn’t take on a long “E” sound. At 4,500 square feet, this unexpectedly large indie bookshop is likely the second biggest in all of Oregon after Portland’s notorious Powell’s City of Books, the largest independent bookseller on Earth. Here, you’ll find fantastic sections for fiction, cookbooks, biographies and children’s books. The front section for field and travel guides includes everything you may need to explore the area better, from hiking guides to fishing spots to even how to make the most of #vanlife. 

Sisters is a haven for artists, so naturally, there are galleries galore. The newest is the Flying Horse, owned and curated by Sloane Earl. The gallery’s motto is “Fantasy. Whimsy. Nostalgia.” Much of the art hanging is from Earl herself and her father, Brad Earl, where acrylic depictions of anything from vintage typewriters to cowboys riding into the sunset, where UFOs loom large, because why not, abound. The gallery-to-saloon ratio is seemingly two to one in Sisters.

Just a block away, the Rickards Gallery caters to high-end art collectors. From the moment you walk through the intricately carved wooden door, you're welcomed into a cozy, nature-inspired setting filled with various artwork, including paintings, stained glass and handcrafted items ranging from jewelry to baskets. Foraged antlers embellish many of the crafts on display. 

One standout feature that consistently draws visitors back is the culinary arts; the gallery also serves as The Open Door Wine Bar, where reservations are recommended. Diners may be seated in the compact dining area, at the well-stocked bar, or in the gallery among beautiful landscape paintings. The menu is hyper-local and refreshingly seasonal. In winter, try the grilled pork chops braised in hard apple cider and paired with the Frosted Sister cocktail, which includes locally distilled vodka, pomegranate and black tea.

Directly across the street is Sisters Coffee Company. While the roasting element of the business has moved several blocks to the north, the space is now a large café with wood-paneled walls, a balcony with branches for banisters, and plenty of trophy bucks and bears peering down on patrons. The coffee and espresso drinks are top-notch, and seasonal lattes like the one that smacks of fresh-baked banana bread are not to be missed.

A few blocks away is The Belfry, a stunning new music venue inside an old church originally constructed in 1914. While the Sisters Folk Fest draws thousands of music fans to the town every September, filling the air with live music from nearly every corner, The Belfry features a diverse lineup. One night, you might enjoy a swing band, followed by an R&B trio the next and a Scottish folk band days later.

Practically next door is Preston Thompson Guitars. Although founder Preston Thompson sadly passed away in 2019, his entirely handmade custom guitar shop continues to thrive. The skilled craftspeople here produce only about 100 guitars yearly, with custom orders typically requiring a year-and-a-half waiting period. Touring musicians like Billy Strings can attest that these acoustic guitars, modeled after the classic Martin Guitars of a century ago, are built to stand the test of time. Whether crafted from Mahogany or more exotic woods like Brazilian Rosewood, these six-strings are true works of art, complete with custom inlays. The small shop usually hosts open-house jams on Wednesday evenings, and space tours are available by appointment or request. If you're a bluegrass fan, be sure to swing by!

The Barn is a communal gathering spot with a dozen taps mainly dedicated to local brews and a small but impressive selection of wines and cocktails. It offers ample indoor seating, including a semi-insulated, covered and heated patio. However, the true appeal lies in its park-like atmosphere, especially when the weather is nice. You can find almost everyone in town—along with their dogs—enjoying pints and eating food from four food trucks. These include Boone Dog Pizza, which has won several people's choice awards; Rootbound, a woman-owned vegan eatery; Chulitas, serving Mexican-style street tacos; and Pop's, known for its Southern-style barbeque. The mouthwatering aroma from the barbeque alone drives both carnivores and dogs wild.

If you enjoy drinking artisanal beverages straight from the source, visit the new Lazy Z Ranch Wines, located a mile and a half east of downtown. John Herman, a rancher, beekeeper, and mead maker, coined the term "ranch wine" to describe his meads, also known as honey wine. Herman ferments various local honeys, ranging from estate wildflower honey to nectar sourced from a nearby lavender farm. Each type of honey offers a unique flavor, showcasing the distinct tastes of the high desert.

If you enjoy more traditional fermentables, head back downtown to discover the local favorite, Three Creeks Brew Pub. Established in 2008, it is older than 20 other breweries that have emerged in Bend and Central Oregon. Three Creeks began as a brewpub and later expanded into a full-production and packaging brewery. However, the changing landscape of the craft brewing industry has led the company to revert to its original brewpub model, which has proven to be a positive change.  

The pub also serves as a true communal hub, featuring a family-friendly side on the left and a 21+ saloon side on the right to cater to different patrons. The delicious food menu heavily focuses on pizzas, including the Metolius Meatlovers, named after the nearby Metolius River, renowned for hiking and fishing. They also offer burgers, such as the classic All-American, and they surprise guests with unique options like the Greek Gyro burger, which is topped with tzatziki, feta cheese, and red onion and served in a pita instead of a bun. There are plenty of small-batch beer options available. You can always count on the flagship brews, such as Hoodoo Voodoo IPA, Raptor Rye IPA (which offers a spicy kick alongside the piney hop bitterness) and the Fivepine Chocolate Porter, known for its rich and robust flavor.

Sisters is an easy day trip from Bend or Redmond, but for those who want to linger longer, FivePine Lodge and Spa, located next to the brewpub, offers rustic lodges and cabins. The lodge has several amenities, including access to the Sisters Athletic Club for guests. Upon entering, you’ll be greeted by a crackling fireplace that adds warmth to the atmosphere. For those interested in fishing, a wide selection of flies is available for fly fishing. If you’re seeking other activities like snowshoeing or snowmobiling, you’ll find a wall of brochures with various options.

For a more boutique-style accommodation, The Scout Cottages provide an intimate and luxurious experience. This collection of six cottages combines a traditional cottage feel with contemporary design elements. Equipped with high-end amenities such as heated floors, king-sized beds, fireplaces and kitchenettes, these cottages are perfect for a romantic getaway or a relaxing retreat. They are centrally located in Sisters, within walking distance of restaurants and shops, and just a short drive from all the activities Central Oregon has to offer.

If you venture just under a half-hour drive into the Deschutes National Forest, you’ll reach Suttle Lake Lodge. This lodge is on a beautiful lake, perfect for outdoor recreation every season. If Mt. Bachelor feels crowded or its ticket prices are too high, consider Hoodoo Ski Area, located up Highway 20. Although smaller, it features steeper runs, costs about half as much as Bachelor and has a reputation as a laid-back party spot.

For those interested in cross-country skiing, the Three Sisters mountains—originally named Faith, Hope, and Charity—are now commonly referred to as North Sister, Middle Sister and South Sister. Being the tallest and least eroded, South Sister is particularly favored for hiking and cross-country skiing. With so much delicious food to enjoy and plenty of snow to play in, the town of Sisters is an inviting destination.

Sisters Bakery; 251 E. Cascade Ave., Sisters; (541) 549-0361; open Monday through Thursday from 6 a.m. to 3 p.m. and Friday through Sunday from 6 a.m. to 4 p.m.; sistersbakery.com.

Ski Inn Taphouse and Hotel; 310 E. Cascade Ave, Sisters; open Monday through Saturday from 11 a.m. to 8 p.m. and Sunday from 11 a.m. to 3 p.m.; sisterstaphousehotel.com.

Dixie’s; 100 E. Cascade Ave, Sisters; (541) 549-6451; open Sunday through Thursday from 10 a.m. to 5 p.m. and Friday and Saturday from 10 a.m. to 6 p.m.; dixies.com.

Alpaca By Design; 140 W. Cascade Ave, Sisters; (541) 549-7222; open daily from 10:30 a.m. to 4:30 p.m.; alpacabydesignshop.com.

Paulina Springs Books; 252 W. Hood Ave, Sisters; (541) 549-0866; open Monday through Saturday from 9:30 a.m. to 7 p.m. and Sunday from 9:30 a.m. to 5 p.m.; paulinaspringsbooks.com.

Flying Horse Gallery; 161 S. Elm St, Sisters; (541) 904-0159; open Thursday through Sunday from 11 a.m. to 5 p.m.; flyinghorsegallery.com.

The Rickards Gallery; 303 W. Hood Ave., Sisters; (541) 549-4994; open Tuesday through Saturday from 10:30 a.m. to 8 p.m.; therickardsgallery.com.

The Open Door; 303 W. Hood Ave., Sisters; (541) 549-6076; open Tuesday through Thursday from 11:30 a.m. to 7:30 p.m. and Friday through Saturday from 11:30 a.m. to 8 p.m.; opendoorwinebar.com.

Sisters Coffee Company; 273 W. Hood Ave., Sisters; (541) 549-0527; open daily from 6 a.m. to 5 p.m.; sisterscoffee.com.

The Belfry; 302 E. Main Ave., Sisters; open only during events. Check belfryevents.com for upcoming events and tickets.

Preston Thompson Guitars; 352 E. Main Ave., Sisters; (541) 588-6211; open Monday through Friday from 9 a.m. to 5 p.m.;  pktguitars.com. 

The Barn in Sisters; 171 E. Main Ave., Sisters; (541) 904-4343; open Sunday through Thursday from 11 a.m. to 8 p.m. and Friday through Saturday from 11 a.m. to 9 p.m.; thebarnsisters.com.

Lazy Z Ranch; 68540 E. Hwy. 20., Sisters; (541) 588-5299; open by appointment only in the winter and spring; lazyzranch.com.

Three Creeks Brewpub; 721 S. Desperado Ct., Sisters; (541) 549-1963; open daily from 12 p.m. to 8 p.m.; threecreeksbrewpub.com.

FivePine Lodge and Spa; 1021 E. Desperado Trail, Sisters; (541) 549-5900; open daily; fivepine.com.

The Scout Cottages; 560 E. Main Ave., Sisters; (541) 527-0815; open daily; thescoutsisters.com. 

The Suttle Lodge & Boathouse; 13300 Hwy. 20, Sisters; (541) 638-7001; open daily; thesuttlelodge.com.