A good city can make a great trip. After all, cities are where you’ll find restaurants and eateries for your whole crew, charming overnight stays, attractions for all ages, and access to outdoor excitement. And in Central Oregon, you’ll find some of the best small cities in the state—hosting lavish resorts, fairs and festivals, local landmarks, stunning landscapes, and more.
To help you plan your next trip, we’ve broken down some of the best cities in Oregon—along with what makes each so special and what you’ll find across the region. Some of our many highlights include:
Bend: The Outdoor Recreation Hub
With a population of about 105,000, Bend is undeniably one of the top cities to visit in Oregon. The region’s largest city exudes a kind of relaxed, cozy charm on sun-kissed hiking trails, brewpub patios, a bustling downtown core, and well-kept parks across the community.
Start your adventure planning with our guide to hiking trails in Central Oregon—many of which sprawl out across (and around) Bend; highlights include a short jaunt to the summit of Pilot Butte State Scenic Viewpoint for 360-degree views, a loop around the bucolic Shevlin Park, and—in summer—a day hike on the scenic Green Lakes Trail. Just west of Bend, Mt. Bachelor Ski Resort is the seventh largest ski resort in North America; it’s winter season typically runs between late November and late May, and its summer offerings include mountain bike trails and scenic lift rides. For a more laid-back adventure, get on the water and float the Deschutes River in Bend. After a fun day outdoors, sample the output from creative chefs at the top restaurants in Bend—and unwind with a flight or nightcap at one of the dozens of breweries and cideries around the city. Visit Bend for more fun suggestions—indoors and out—around one of the most beautiful cities in Oregon.
If you’re curious about Bend’s other charms, dive into the best of the city with our article: Why is Bend So Popular?
Redmond: Gateway to Central Oregon
When you visit Redmond (pop: 37,000), you are firmly in the heart of the Central Oregon high desert. Just outside of town, stretch your legs on the trails at Smith Rock State Park (where sheer rock faces rise dramatically from the banks of the Crooked River), Steelhead Falls (where a short hike leads to a wide cascade in the Deschutes River), and Cline Falls State Scenic Viewpoint (home to a short trail that leads to a viewpoint overlooking a series of rocky rapids in the Deschutes River). Juniper trees and sagebrush bushes dot the landscapes at each park, and Cascade peak views rise to the west.
Back in town, a number of brick buildings line the city’s downtown core, hosting a number of antique shops, boutiques, breweries and cideries in Redmond, and numerous restaurants and food carts dishing fare from around the world. Get inspired for your trip with our article on why Visit Redmond, Oregon.
Redmond is also where you’ll find the Redmond Municipal Airport (airport code RDM). Read our article on getting to Central Oregon for information on flying into the region—where adventure begins as soon as you leave the terminal.
Sunriver: Where Adventure Meets Tranquility
Get away from it all at Sunriver, a popular resort community that offers a little something for everyone—cozy escapes for solo travelers in search of solitude, couples on romantic getaways, and families excited to explore the best of Central Oregon. With so much to see and do, it’s no wonder that Sunriver is routinely cited as one of the best small cities in Oregon.
Make plans to stay at Sunriver Resort, which is the heart of the community (pop: 1,500); there, you’ll choose among well-appointed lodge rooms and vacation rentals for groups of all sizes. The resort’s many offerings include four world-class golf courses (each offering wide-open mountain views); summertime horseback rides through the forests and meadows surrounding the resort; and bike, kayak, and stand-up paddleboard rentals in summer.
Just south of town, the Newberry National Volcanic Monument showcases the region’s volcanic history through self-guided lava tube tours, interpretive exhibits, wide-open viewpoints, and more. In winter, the resort’s Traditions programs celebrate the holiday season with idyllic experiences, and Sunriver Resort’s close proximity to Mt. Bachelor Ski Resort makes it a pleasant basecamp for a weekend on the slopes. Bringing the family? The Sunriver Nature Center & Observatory showcase the region’s flora and fauna, as well as awe-inspiring stargazing opportunities, all year long.
Sisters: A Quaint Western-Themed Town
You won’t see any cowboys riding their horses through the heart of downtown Sisters (pop: 3,000), but you’d be forgiven for thinking otherwise. Buildings across the Old West-inspired community are decorated to look like they came out of the late 1800s, and the community embraces its independent spirit with adventures in and around town all year long.
Roughly a dozen art galleries showcase work from regional and nationally renowned artists around Sisters, The Barn hosts an on-site taphouse and a few food carts—all of which pairs well with occasional live performances from local musicians, the McKenzie Pass Highway offers a summertime escape into the nearby Cascade Range, and Hoodoo Ski Area boasts the region’s only nighttime skiing just outside of Sisters. Nearby, the long-running Black Butte Ranch welcomes visitors with well-appointed vacation rentals, a pair of championship courses, and enough on-site activities to keep guests coming back time and again. Learn more about why to visit Sisters, Oregon, for other suggestions, ideas, and inspiration.
If you visit Sisters in summer and fall, your trip might sync up with some of the community’s annual events that bring visitors from near and far. That includes the Sisters Rodeo every June, the boisterous Big Ponderoo music festival in late June, the Sisters Outdoor Quilt Show every July, and the Sisters Folk Festival—where local and national musicians alike perform in venues throughout town every September.
Prineville: Central Oregon’s Iconic City
The city of Prineville (pop: 11,275) earns its iconic status for being the oldest city in Central Oregon—having been founded in 1870. Today, that history is on display in a variety of fascinating ways in and around the city.
Start your adventure at Prineville’s Bowman Museum, where interpretive panels and immersive exhibits describe the town’s earliest days—and explain how it’s remained a pillar of the region for more than 150 years. Jump further back in time at the Painted Hills Unit of the John Day Fossil Beds National Monument, which is about an hour east of Prineville—and which shows off millions of years of ecological change through colorful hillsides dotted in hues of red, gold, black, and brown. Closer to town, Prineville Reservoir State Park sits on the shores of its namesake lake and offers plenty of fun—boating and fishing by day, camping and stargazing by night. When you get hungry, check out the best places to eat in Prineville.
Travel Tips for Visiting Oregon
With so much to do and see, you might not know where to start with Central Oregon vacation planning. Here are a few tips to make that process as smooth and enjoyable as possible—and to make the most of your time in the best cities to visit in Oregon.
Top cities: We shouted out these five cities because each showcases a different aspect of what makes Central Oregon so special; Bend, for instance, is a hub of outdoor recreation—while Sunriver is an ideal destination for families and Prineville shows off regional history. See what sounds most appealing to you and your crew, and make plans to base yourself in that particular city. Learn more about where to stay in Central Oregon for overnight accommodations in each community.
Drive time: Can’t decide? That’s okay: Broadly speaking, the cities and attractions we shouted out here sit within about one hour of each other—making each a fun day trip from your basecamp. Wherever you go, you’ll find plenty to enjoy; after all, that’s why we dubbed them some of the best cities in Oregon.
Seasonal planning: In winter, snowy outdoor fun—including snowshoeing, cross-country skiing, snowmobiling, and downhill skiing and snowboarding—is one of the top draws around Central Oregon; come summer, sun-dappled skies offer ideal conditions for hiking, mountain biking, paddling, and floating the Deschutes River. When choosing when (and where) to visit, consider the activities you’d most like to enjoy—and plan accordingly. Keep in mind that snowy weather in winter may impact road conditions; visit TripCheck.com for webcams, traffic alerts, road closures, and other important information.
Other stories
More inspiring stories, adventures, and tips & tricks for planning and experiencing the best Central Oregon has to offer.
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Best Mountain Towns in Oregon
There’s something magical about visiting a charming mountain town. You get to spend your days hitting the slopes, hiking trails to stunning viewpoints, or paddling crystal-clear alpine lakes. You can while away an afternoon around the fire pit at a neighborhood brewpub, then you can take an evening to dine at cozy restaurants and enjoy historic downtown cores—all with snow-capped peaks towering above.
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Top Ski Resorts and Lodging Near Bend, Oregon
When the first snow falls in the Cascade Range every autumn, outdoor enthusiasts across the Pacific Northwest dig out their skis, wax their snowboards, and start planning epic getaways to ski resorts near Bend, Oregon. Across the region, our slopes are dotted with fast-running, dry powder that caters to skiers and boarders of all skill levels—with a season that begins as early as November and continues until Memorial Day in May.