9 Storybook Towns In Oregon

Although fairytales often seem set in distant lands, Oregon is full of enchanting towns that lie much closer to home. Surrounded by waterfalls, wine valleys, and lush rainforests, these mystical destinations feel straight out of a storybook. Ready for a magical adventure? These nine towns will make you feel like you have stepped into a real-life fairytale.

Silverton

Known as “Oregon’s Garden City,” there are hundreds of acres of gardens and outdoor beauty to appreciate in Silverton. Enjoy an afternoon at the Oregon Garden, a botanical garden covering over 80 acres that represents the diversity of the region’s plants. Silver Falls State Park is another must-visit nearby, featuring several miles of trails that lead to 10 stunning waterfalls. After exploring Silverton’s great outdoors, grab a burger and beer at Mac’s Place, a beloved local pub, or enjoy a hot bowl of ramen at Fin + Fowl, an Asian restaurant with a French and Californian twist.

Jacksonville

Located in the heart of the Applegate Wine Valley, Jacksonville is a historic town shaped by the 19th-century gold rush. One of the most charming ways to learn about Jacksonville’s history is on a trolley tour, a 45-minute tour that highlights the historic commercial buildings and vintage homes, all while on board one of Jacksonville’s historic trolleys. To learn more about the life of early pioneers, visit the Beekman House, formerly the home of the prominent pioneer C.C., Beekman and still furnished with the family’s original furnishings. After learning about Jacksonville’s interesting past, finish off the day with a glass of wine at one of the nearby wineries, such as Somar Family Vineyards, a family-owned establishment offering tastings of its locally crafted wines.

Redmond

Redmond is a lively town year-round, energized by a bustling brewery and music scene. Throughout the year, the town hosts a variety of music festivals, particularly in the warmer months. Some of these events include the Fairwell Festival, held in July, Music on the Green, a block-party music event that takes place from June through September, and the Cascade Equinox Festival, a music and arts festival taking place in September. To enjoy the town’s brewing scene, check out local gems such as Initiative Brewing and Wild Ride Brewing. Those visiting in the winter months can hit the nearby slopes, with Mt. Bachelor Ski Resort being one of the most popular as the Pacific Northwest’s largest ski resort.

Yachats

The charming coastal town of Yachats, home to just over 1,000 residents, sits within Oregon’s temperate rainforest along the shores of the Pacific Ocean. Visitors can take in breathtaking views at the Cape Perpetua Scenic Area, Oregon’s highest car-accessible viewpoint, towering 800 feet above sea level.

For those eager to head outdoors, the area offers numerous coastal hiking trails. One standout is the 804 Trail, which meanders along the ocean before descending to a seven-mile stretch of sandy beach. Along the way, hikers might spot native wildlife, including deer, elk, and migrating seabirds. To fully immerse yourself in the outdoors, consider staying at Ambrosia Gardens Bed and Breakfast, a cozy, antique-furnished inn between Searose Beach and the lush Siuslaw National Forest.

Florence

Florence has a diverse range of ecosystems and natural attractions, from coastal sand dunes and serene lakes to the famous Sea Lion Caves. Take a tour of this impressive site—the largest sea cave in the United States—home to hundreds of sea lions. While in the area, visit the historic Heceta Head Lighthouse, which has guided ships since 1894 from its position atop the 1,000-foot-high Heceta Head. For an unforgettable outdoor experience, head to the Oregon Dunes National Recreation Area, where visitors can stand on towering 500-foot sand dunes, appreciating unique panoramic views of the Pacific Ocean on one side and a group of lakes on the other.

Cannon Beach

Cannon Beach is renowned for its iconic Haystack Rock, a 235-foot basalt sea stack that draws visitors from around the globe. During low tide, explorers can wander around its base, discovering tide pools teeming with marine life and catching glimpses of puffins. Beyond the beach, outdoor enthusiasts can enjoy scenic coastal hikes at Ecola State Park or venture through the lush coastal rainforest of Oswald West State Park. After a day outdoors, stroll through some of Cannon Beach’s impressive art galleries, including DragonFire Gallery, Icefire Glassworks, and Bronze Coast Gallery.

Hood River

Known as the “Windsurfing Capital of the World,” Hood River is the perfect destination for those wanting to hit the water. Rent a sail with Northwave Sails or Big Winds and head to the Columbia River Gorge for an eventful day. Not interested in windsailing, but still want to appreciate the outdoors? Enjoy a scenic walk along the Hood River Waterfront Trail, a 2.5-mile paved path that stretches along the marina and arches over the river. After your morning of wind sailing or walking, head over to Camp 1805, a distillery and tasting room situated along the bank of the Columbia River that produces hand-crafted cocktails and spirits.

Sisters

Sisters is most well known for its annual rodeo, which takes place during the second week of June each year and features classic events such as bronc riding, steer wrestling, barrel racing, bareback riding, and bull riding. The small town is also popular for camping and hiking, sitting on the edge of the 1.6 million acre Deschutes National Forest, filled with lakes, rivers, hundreds of miles of hiking trails, and starry nights. For a more comfortable place to stay, consider lodging in one of Sister’s cozy lodges, such as FivePine Lodge & Cabins, a rustic bed and breakfast style lodge rated as one of the state’s best accommodations.

Joseph

Joseph is one of Oregon’s best mountain towns, sitting at the base of the Wallowa Mountains near canyons, rivers, and alpine lakes. Wallowa Lake State Park is a great outdoor recreational destination year-round, featuring a 200-site campground, a boat launch for those wishing to explore the lake, and a beach for lounging in the sun in the summer. Those wanting to venture further into the wilderness must explore the Eagle Cap Wilderness, home to glacial valleys, forested rivers, and bare granite peaks. For a burger or steak in a Western-style atmosphere, grab a bite at Stubborn Mule Saloon & Steak, a beloved restaurant in town with both indoor and outdoor seating.

Final Thoughts

In the state of Oregon, a magical escape is never far away. From alpine lakes and historic lighthouses to expansive botanical gardens and western-style rodeos, unforgettable experiences are always just around the corner. So get ready to step into your own story and discover the beauty that these nine towns have to offer!