A charming place located in southern Oregon, Ashland is a friendly town offering guests much to see and explore. Situated where the Siskiyou and Cascade Mountains converge, the lush area is brimming with scenic views, outdoor adventures, historical sites and many art and cultural experiences. Must-do activities include taking a leisurely stroll through the Historic Downtown and Railroad Districts where beautiful buildings filled with unique shops, galleries, and cafes are waiting to be discovered. In addition, it is worth meandering through the stunning Lithia Park, which features 90 acres of serene beauty. After a day of walking, enjoy a theatrical production by the renowned Oregon Shakespeare Festival—currently in its 80th year.
Situated on the Columbia River in Northern Oregon, Astoria is a picturesque town found just a few miles from the Pacific Ocean. The oldest U.S. settlement west of the Rocky Mountains, the area exudes charm around every corner with its stunning Victorian homes and beautiful landscape. Surrounded by forests, mountains, plus rivers, Astoria offers something for everyone from outdoor enthusiasts to history buffs to foodies and more. Kayaking, visiting the Columbia River Maritime Museum or the Lewis and Clark National Historical Park, sampling fresh seafood, or shopping for an eclectic array of gifts are just some of the activities you can do in town. Many events take place throughout the year as well, including the Goonies 30th anniversary celebration in June
Located in eastern Oregon, Baker City is a scenic town situated along the Historic Oregon Trail. Guests can explore the town’s Historic District where they will not only receive a glimpse into Baker City’s past through its buildings, but also discover many great businesses from restaurants to unique shops. For a deeper look into Baker City and the surrounding area’s history, the Baker Heritage Museum and National Historic Oregon Trail Interpretive Center are two must visits. For those visitors wanting to experience a bit more adventure, there are plenty of hiking trails in the area along with cycling and fishing opportunities.
Brownsville is a lovely community nestled in the foothills of the Cascade Mountains. Settled in 1846, the town is like taking a step back in time as things remain very similar to how they were several decades ago. Featuring an historic downtown area with buildings from the late 1800s and early 1900s, the town also has many historic homes plus a beautiful 26-acre park, Pioneer Park. Film buffs can meander this quaint gem on foot and discover locations where Stand By Me, a 1980s movie, was filmed. The Moyer House, an Italian villa-style home, now a historic house museum, is another must-see when in Brownsville.
Known as the ‘covered bridge capital of the west’—the area boasts seven covered bridges in and around town—Cottage Grove is another little charmer brimming with beauty. Featuring a lovely downtown area, which is perfect for exploring by foot, the town has many century-old buildings, many of which house art galleries, boutiques, and cafes. History lovers may want to visit the Bohemia Gold Mining Museum, which explores the region’s gold mining history, or the Oregon Aviation Historical Society while art buffs will enjoy seeking out stunning murals found on buildings throughout the area. Its location also provides many activities for adventure seekers, including hiking, cycling, and horseback riding.
A coastal escape, Florence is a beautiful town with an abundance of scenic views—both oceanic and forest—and fun adventures. Visitors with a need for outdoor excitement can rent a dune buggy and explore miles of sand dunes along the coast within the Oregon Dunes National Recreation area. For those seeking a different sort of outdoor fun, a hike to the Heceta Head Lighthouse, which provides some incredible panoramas, is a wonderful choice. The town is also home to the lovely and vibrant Historic Old Town, which is set along the Siuslaw River and features art galleries, boutiques, antiques, and restaurants. Florence also hosts many exciting events throughout the year.
Located in the stunning Columbia River Gorge, Hood River is a lovely and vibrant town with beautiful views at every turn. From breathtaking mountains topped with snow to fields of wildflowers to waterfalls to orchards, the area offers a diverse range of scenery that will entice anyone’s inner photographer. The location also provides plenty of outdoor activities from hiking to white-water rafting, and more for those who love to play in the open air. Foodies will also take a great interest in Hood River with its award-winning craft breweries, wineries, and restaurants that focus on creating mouthwatering delights featuring the area’s bounty. Visitors can find incredible arts and crafts and other unique items in the downtown area as well.
A National Historic Landmark, Jacksonville is a picturesque town with its past rooted in the gold rush. With over 100 buildings on the National Register of Historic Places, the town is perfect for taking historic tours. Wander through the neighborhoods to take in the beauty of Victorian-style homes or visit the charming brick and wooden buildings lining the streets of downtown to explore boutiques, restaurants, and more. For the nature lover, hiking some of the Jacksonville’s Woodland Trails is a definite must-do. The town is also a great base from which to explore the area’s wineries as it’s situated at the entrance of the Applegate Valley Wine Country.
With a rich Native American history, Joseph—named after Nez Perce Chief Joseph—is a charming town in northeast Oregon. The area is not only a history lover’s haven but also an outdoor enthusiast’s paradise with the stunningly beautiful Wallowa Mountains and Eagle Cap Wilderness nearby. Often referred to as the ‘Little Switzerland of America,’ the area offers miles of hiking trails, which vary from easy to difficult. Main Street in town is lovely to wander with its shops, galleries, and dining establishments. Art lovers will also be impressed with the bronze sculptures, by artists including Shelley S. Curtiss and Steve Parks, that line Main Street.
Located in central Oregon near the volcanic peaks known as Three Sisters, Sisters is a lovely town whose roots are firmly planted in ranching, farming, and logging. Just as with so many of the beautiful places already mentioned, Sisters is also a place to enjoy the great outdoors through a variety of activities, as the Deschutes National Forest is nearby. Paying homage to its past, the quaint downtown area is Western themed and home to many specialty stores, tasty cafes, and galleries. With a thriving arts scene, Sisters hosts several art events throughout the year, including the Sisters Folk Festival and Sisters Outdoor Quilt Show, which is the largest outdoor quilt show in the world.