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Painted Hills

Road Trip from Pendleton to the Blue Mountains

Pendelton Round Up
Written by Oregon Media

Road Trip from Pendleton to the Blue Mountains

A historic rodeo, a cultural center devoted to the Confederated Tribes of the Umatilla Reservation, a famous whisky, and one of the newest viticultural areas in the United States round out this road trip

Pendelton Wooden Mills Pendleton epitomizes the wild west, with an authentic western frontier downtown and events and destinations celebrating the history of Native Americans and pioneers alike. Begin your Pendleton experience underground with a Pendleton Underground Tour, which takes guests into a network of rooms and passageways of Pendleton’s red-light district. Learn about local Chinese immigrants and their role in building Eastern Oregon, and hear true tales of brothels, bootlegging and gambling. Knowledgeable historians lead these tours, which have been featured on television and radio shows around the world.

over a century and Counting

What began in 1910 as a small gathering of local cowboys has grown into one of the largest and most revered rodeos in the country. Each year, the Pendleton Round-Up kicks off with the Dress-Up Parade and ends with crowning rodeo champions. One of the specialty events is the Happy Canyon Indian Pageant, a nightly theater production about Native Americans with roots in the region, and the formation of Pendleton. Year-round, visit the Pendleton Round-Up and Happy Canyon Hall of Fame, a museum devoted to the rodeo and its legacy.

Trains, Camps and Signs of the Past

Also downtown is the Heritage Station Museum, located in a 1909 Train Depot, featuring a one-room schoolhouse, homestead cabin and barn, windmill and a train caboose. See exhibits on the Oregon Trail and the search for “Umatilla Gold”—wheat, that is. For another glimpse of the past, journey to the corner of First Street and Frazier to Emigrant Camp, where pioneers on the Oregon Trail made temporary base camp as they gathered supplies before carrying on to the Willamette Valley.

An Artist’s Touch

On the east end of Pendleton sits the Pendleton Woolen Mills. Founded in 1863, the Pendleton mills have made their mark with beautiful color and original patterns for nearly 160 years. Visit the Woolen Mill Store for the largest selection of jacquard blankets and array of Pendleton wool fabrics, remnants and mill ends, as well as tours offered during weekdays.

For more local artisanship, visit the Pendleton Center for the Arts in a beautifully restored 1916 Carnegie Library building overlooking the Umatilla River. Inside, browse the galleries, shop for finely crafted wearable and functional art, enroll in a free or low-cost class, or take in a live music, literary arts or dance event. Regional works are for sale—take home a very special souvenir of a work of art made by an Eastern Oregon resident.

Tero Estates

Fruits of Our Labors

There’s tons to see and taste on the Whisky and Rocks Farm Loop. Wine, fruit, cider, cheese, beer, berries, whiskey and more are all to be discovered along this route offering the best of the Milton-Freewater and Pendleton bounty. Take your time on the tour and drink in the tastes to be savored.

Pendleton’s Delicious Delights

With so many local farms, it’s no surprise Pendleton has amazing culinary options. Visit Barhyte Specialty Foods, a family operation with 30 years’ history creating delicious mustard, marinades, sauces and hard seltzers. The Great Pacific Wine and Coffee Company has an extensive food menu, wine and beer selection, and full espresso bar, using fresh, locally sourced ingredients.

Opening in 2006, Hamley’s Steakhouse & Saloon became a mainstay in downtown Pendleton. The Western-style restaurant is a step back in time with great food. Virgil’s at CIMMIYOTTI’S has been a Pendleton tradition since 1959. Famous for steaks, red velvet wallpaper, horseshoe curved booths, and classic drinks from the bar, this iconic restaurant delivers impeccable food and legendary service.

Prodigal Son Brewing A Pint or a Dram

Pop into Prodigal Son Brewing for a taste of local brew. Three hometown locals opened this brewhouse—the first in Pendleton—in 2007. The from-scratch kitchen crafts a menu chock full of local products, from meats to cheeses to baked goods. Down the street the Oregon Grain Growers Brand Distillery makes spirits from local grains, showcasing the agricultural history and pride of farming in the area. The farmer-owned distillery mills grain on-site and connects visitors to the agricultural legacy of the area by way of high-quality spirits.

casino fun built on tribal history of gaming

Wildhorse Resort & Casino is the largest resort in Eastern Oregon with a casino, more than 300 hotel rooms, a cineplex, a sports bar, restaurants, a bowling alley, RV park and events center. The resort also hosts an annual Pow Wow in July.

With sweeping views of the Blue Mountains and an upscale yet comfortable ambience, Plateau Restaurant at the Wildhorse Casino offers Northwest fare featuring the best cuts of meat and freshest ingredients, along with regional wines and cocktail creations. Don’t miss a round of golf at Wildhorse Golf Course, an 18-hole championship course featuring pristine greens amid dramatic natural landscape and rolling wheat fields.

Tamastslikt Cultural Institute Next door is Tamástslikt Cultural Institute, built by the Confederated Tribes of the Umatilla Indian Reservation to preserve the culture and history of the Cayuse, Umatilla and Walla Walla Tribes and present their story to the world. The state-of-the-art facility showcases regional tribal history, the tribes’ present-day affairs and plans for the future through interactive exhibits, Coyote Theater, events, programs and quarterly exhibitions on timely topics. Shopping at The Museum Store and dining at Kinship Café round out the visit.

Nearby, shop for indigenous art at the gallery at Crow’s Shadow, a nonprofit contemporary printmaking studio on the Confederated Tribes of the Umatilla Indian Reservation.

A Wildlife Haven

South of Pendleton, nestled between the plains and the mountains, McKay Creek National Wildlife Refuge is habitat for rare and endangered species and a haven for breeding and migratory birds. There’s something for everyone: hunt, drive, hike and observe the abundant wildlife and scenic beauty at this important protective site.


Motorcycle enthusiasts adore Oregon’s smaller highways and the amazing scenery that goes with them, alongside light traffic and friendly people and businesses along the way. Every third weekend in July, Pendleton Bike Week hosts its annual Rally & Races with the support of local businesses and surrounding communities welcoming all motorcycle enthusiasts.

Blue Mountain Scenic Bikeway Clip In

Bicyclists are equally enchanted with this landscape. The rolling and waving wheat fields of Umatilla County and the glorious peaks of the Blue Mountains provide a peaceful and stunning backdrop to a ride. Enjoy an easy loop east of Pendleton or explore the rolling fields around Athena and Helix. Take in the breathless views and challenge of the Cabbage Hill Climb.

The climb is celebrated annually at the Century Ride of the Centuries, a one-day ride up Cabbage Hill. The out-and-back ride starting from and returning to the Pendleton Chamber of Commerce parking lot explores the rolling hills of the Umatilla Basin on this challenging day in late May.

Trails and Greens

Unpaved trails for the cyclist or hiker are found at Pendleton Adventure Trails Recreation Area, just northwest of Pendleton. A variety of easy-to-moderate trails for runners, hikers, and mountain bikers are here, with a south-facing exposure that offers plenty of year-round sunshine.

Seven miles south of Pendleton on Highway 395 is the Birch Creek Golf Course, owned and operated by the Umatilla Tribes. Enjoy 18-holes of golf, practice facilities, a full bar and restaurant, and newly remodeled banquet room.

An Old Terroir Named New

Milton-Freewater sits at the northern Oregon border, a small town of the Walla Walla Valley, which extends south from Washington state. This fertile land is not only excellent for growing produce, but also fabulous terroir for wine grapes. One of the nation’s newest American Viticulture Areas, the Rocks District AVA was designated here in February 2015. Predicated on one soil series and one landform, the terroir consists of riverbed rocks that give the wines a characteristic flavor profile, particularly noticeable in syrah.

A Vintner’s Heaven

Watermill Winery Milton-Freewater is home to many wineries. Start your day of sipping at the historic Watermill Building to taste the fruits of Watermill Winery, founded in 2005 by commercial apple growers who had been farming in the Walla Walla Valley for more than a century and pledged to grow wine grapes using sustainable and wildlife-safe farming practices. Visit Spofford Station, an historic grain farming site, to try bold wines that reflect the earthy wash of thousands of years of basalt, ash and mineral.

Rotie Cellars, Tero Estates and Cayuse Vineyards sit on the west end of Milton-Freewater. Try a glass of Tero Estate’s love letter-worthy cabernet sauvignon, regularly scored above 90 points by Wine Enthusiast. Cayuse Vineyards produces critically lauded biodynamic wines including syrah, cabernet sauvignon and cabernet franc. Rotie Cellars pays homage to the wines of the Rhône Valley, and each year, a new vintage of the northern and southern red and white blends is released.

On to Zerba Cellars on the north end of Milton-Freewater, a log cabin tasting room that could pass as a pioneer homestead. Inside, taste award-winning wines grown on three estate vineyards. Nearby, at Castillo de Feliciana Vineyard & Winery, Spanish-style wine is served at a lovely little tasting room with plenty of scenic outdoor seating. Los Rocosos Vineyards is another outstanding stop for wine and views.

Dragon's Gate Brewery Dragon’s Brew, Blue Cider and Lavender Chocolate

Blue Mountain Cider Company It’s not just about wine in Milton-Freewater. Find small-batch craft brews at Dragon’s Gate Brewery, a farmhouse brewery that focuses on estate-grown hops and spring water tapped from a deep natural spring onsite. Set on a 10-acre farm amongst orchards, vineyards, and fields of wheat, Dragon’s Gate Brewery brews farmhouse and Belgian style ales steeped in tradition. Downtown at Blue Mountain Cider, taste premiere cider made from apples grown right here. The Freewater Cider Company challenges conventional practices by fermenting whole apples on skins to enhance the aromatics and flavors, and then oak barrel aging the drinks.

Petits Noirs Fine Chocolates creates chocolates inspired by locally grown herbs and spices, with flavors such as anise, lavender, rosemary, clove, and violet. Chocolate goes great with wine, and so does cheese. Grab some gouda, havarti or cheddar at The Walla Walla Cheese Company. The Umapine Creamery in the small community of Umapine west of Milton-Freewater produces more delightful cheeses, crafted from the milk of their very own cows.

For local heritage and history, visit Frazier Farmstead Museum. This charming, scenic home and farm built in 1892 serves as a museum dedicated to the history of Milton-Freewater. Not far away is the Milton-Freewater Drive-In Movie Theater. This classic drive-in theatre has been in operation for six decades and is open late spring through October.

Oupost Farm Stand Campout in the Famous Blues

Before you leave the area, travel southeast of Milton-Freewater into the legendary Blue Mountains. Find camping spots at Harris Park or Umatilla Forks Campground. Visit the Outpost, a farm stand located as you ascend out of the town of Weston up into the Blue Mountains. Stop in for fresh produce and homemade baked goods. The Alpine Outpost is located near the summit of the Blue Mountains in the little hamlet of Tollgate. A restaurant, bakery, coffee house and small store greet the traveler and adventurer.