Central Oregon's Oldest City Is A Hidden Paradise Surrounded By Guest Ranches In The Painted Hills

Central Oregon is home to some of the state's most charming and scenically beautiful destinations. From quiet, artsy towns boasting year-round activities and breathtaking mountain views like Sisters to vibrant cities brimming with craft beer, art, and outdoor adventure like Bend — which is also home to the world's last remaining Blockbuster Video — there are plenty of gems to explore in the heart of the Beaver State. Situated about 35 miles northeast of Bend is an oft-overlooked city, and Central Oregon's oldest, Prineville.

Dating back to 1870, the historic High Desert city has all the trappings of a drive-through town. Its main drag is dotted with classic chain hotels and fast food restaurants, seemingly encouraging a quick stay en-route to elsewhere. However, it's Prineville's surrounding beauty that renders it a desirable destination. Explore the vibrant landscapes of the Painted Hills, take a scenic drive along the Crooked River, and nestle into idyllically rustic lodgings at one of the ranch resorts bordering the city. If you're longing for a laid back getaway that combines small town charm with big outdoor beauty, Prineville is the prime spot for your next Central Oregon vacation.

If you're traveling by plane, flying into the Redmond Municipal Airport (RDM) in Redmond — an underrated and rugged city that's considered the hub of Central Oregon — will land you about 20 miles west of Prineville, making for a half-hour drive to your destination. While the town itself has a modest array of attractions, it's a great spot to fuel up on food before embarking on outdoor adventures. Since Prineville is surrounded by acres of farmland and cattle ranches, the city has a robust bar and grill scene. A local staple since 1942, Club Pioneer serves up mouthwatering cuts of prime rib and cowboy cocktails in a saloon-style facade. For BBQ classics, gourmet burgers, and craft beer, grab a table at Dillon's Grill. For a quick bite and a caffeine buzz, swing by Prineville Coffee Company on your way.

Situated about an hour east of Prineville, The Painted Hills are one of Oregon's most unique natural wonders. Composed of miles of colorful hillscapes formed 35 million years ago, the geographical marvels flourish in vibrant stripes that come in shades of red, orange, tan, and gold, giving the painted brush-stroke effect that inspired their name. Admire the breathtaking beauty of the hills on a gentle half-mile Painted Hills Overlook Trail, or take the 1.6-mile Carroll Rim Trail for a steeped climb and panoramic views at the top. Perfect for a day trip from Prineville, the magnificent hills are not to be missed.

While you're more than welcome to check into Best Western and call it a day, Prineville is bordered by two ranch-style retreats that are too idyllic to pass up. Most illustrious is the Brasada Ranch Resort. Located just 20 miles southwest of town, the sprawling oasis sits on 1,800 stunning acres backdropped by the majestic Cascade Mountain Range. Combining scenic beauty with luxury accommodations, the resort boasts beautiful bungalows, suites, and cabins outfitted with rustic chic decor, and lots of activities and amenities to indulge in. Tee up for 18-holes alongside magnificent views at the Brasada Canyons golf course, feel your stress melt away in the onsite spa, and savor delicious farm-to-table dishes while sipping local wines and micro-brews at the Ranch House.

If you don't need all the bells and whistles of a luxury retreat, settle into the Wine Down Ranch. Situated about 12 miles north of Prineville, the family-owned cattle ranch offers a tranquil, unplugged retreat nestled near the Ochoco National Forest. Surrounded by rolling meadows and rocky hills dotted with fresh juniper trees, nestle into a cozy ranch-style bunkhouse or a tiny pine cabin for two. Visit in late-June to catch In A Landscape, an outdoor classical piano concert set against some mesmerizing Central Oregon scenery.