The Most Picturesque Towns In Oregon

It would take hundreds of pages to explore all of Oregon’s beauty. According to Travel Oregon, the state is home to 361 state parks, over 1,400 named lakes, and 11 national forests. Additionally, thanks to the state’s Beach Bill, all of its 363-mile coastline is public! While this article cannot capture everything, it will highlight some of the state’s most remarkable places. The Cascades, river gorges, and waterfalls are a few of the features that make the following eight towns some of Oregon’s most picturesque destinations.

Joseph

Surrounded by the Wallowa Mountains, Joseph has rightfully earned the nickname of the “Little Switzerland of America.” As you might expect, the hikes here are gorgeous. The East Moraine is a favorite among hikers, with a gentle 700-foot incline and a trail that winds past lake views, open grasslands, flower meadows, and more. Wallowa Lake State Park is another great place to spend a sunny day, with a beach, prime fishing spots, picnic areas, and access to the Wallowa Lake Trailhead. If you are up for a bit of a drive, consider making the trip out to the Zumwalt Prairie Preserve. Although this preserve is about a 40-minute drive from town, it is well worth it, home to thousands of acres of vital bunch grass habitats that have almost completely disappeared in other parts of the US.

Newberg

Situated in the heart of Oregon’s Willamette Valley, Newberg is home to some of the state’s most picturesque vineyards. The vineyards in the area are practically endless, and travelers can stop for a tasting at places like Alexana Estate, a local winery with indoor and outdoor seating that looks out over the rolling vineyards below. Bells Up Winery is another beautiful stop, a micro-winery with a tasting room and patio where tastings are available by reservation. To get a bit of exercise after drinking all that wine, consider a hike along the Chehalem Glenn & Gettman Loops, a scenic trail that meanders along a rolling golf course, forest, and creek.

Cannon Beach

Heading to the Oregon Coast, travelers will find the one and only Cannon Beach, famously known for Haystack Rock. This landmark is arguably one of the most famous in the state, rising 235 feet near the edge of the shore and covered in tidepools and diverse bird life. Ecola State Park is another beautiful highlight, extending for nine miles along the coast with spruce forests, grassy bluffs, and, of course, ocean views. Travelers seeking a souvenir to commemorate their picturesque vacation can head to one of the town’s local art galleries, like DragonFire Gallery, which sells original art from the Pacific Northwest region in a variety of media.

Yachats

Travelers looking for an alternative to the popular Cannon Beach will love the small coastal town of Yachats, home to just over 1,000 residents. This area is chock full of beaches, state parks, and hiking trails, making it easy to fill a weekend with outdoor activities. The 804 Trail is one of the town’s most beloved hiking routes, winding along coastal bluffs and offering spectacular views of the ocean. Yachats State Park is a wonderful place to spend a couple of hours as well, sitting near Ocean View Road and acting as a prime location for whale watching. If you’ll be in town in mid-October, consider attending the annual Yachats Mushroom Festival, which celebrates the area’s wild mushrooms with interactive workshops, talks, and guided walks.

Ashland

Ashland sits near the meeting point of the Cascade and Siskiyou Mountains, resulting in some extremely scenic views. There is an extensive list of hiking trails in the nearby radius to explore, such as Grizzly Peak Trail, a family-friendly trail in the Cascade-Siskiyou National Monument. This trail meanders through a mix of pines and firs, providing fantastic views of both Ashland and the Rogue Valley. For a weekend on the lake, travelers might also enjoy a visit to Howard Prairie Resort, which sits on 155 acres with over a mile and a half of lakefront. A few of the recreational activities at the resort include camping, boating, and fishing. As part of the Rogue Valley Wine Country, the vineyards in the area are phenomenal as well! For a glass of wine with a view, stop by Irvine & Roberts Vineyards, which overlooks the Cascade and Siskiyou Mountain foothills.

Silverton

If you love a good waterfall hike, Silverton should be at the top of your travel list. This town is located just a short drive away from Silver Falls State Park, often referred to as the “Crown Jewel” of Oregon state parks. This park is home to South Falls, a 177-foot waterfall with a trail that lets visitors walk behind the cascade for a rare view from the other side! The Oregon Garden is another highlight, featuring over 80 acres of botanical gardens that showcase the region’s biodiversity. Travelers who want to immerse themselves further in nature will enjoy a night at Camp Dakota, a 45-acre campground in the forest that has tent sites, RV sites, and tee pees for rent.

Hood River

Hood River serves as a gateway to the Columbia River Gorge, offering several unique ways to explore its scenery. Bikers and kayakers can arrange a rental through Pedal & Paddle Hood River, a local outfitter that offers e-bike, kayak, and paddleboard rentals to venture through the gorge. To admire the region’s colorful fall foliage, consider booking a train ride on the Mount Hood Railroad, which was voted as one of the top 10 best fall foliage train rides in the country by The Pioneer Woman. The Hood River Orchard & Ale Festival is coming up on October 4th, celebrating the local cider and brewers during harvest season with a lively festival on the waterfront.

Sisters

Sisters is an old western-style town in the heart of the Cascades, providing access to rugged trails, lakes, and riding stables. Travelers seeking a short, easy hike can spend an afternoon on the Whychus Creek Overlook, a one-mile trail leading to a viewpoint atop cliffs overlooking the creek. Those who enjoy boating or fishing can visit Three Creek Lake, where old-growth forest surrounds the water and rentals include paddleboards, rowboats, fishing rafts, pontoons, and canoes, along with fishing gear available on-site. Want to explore the terrain on horseback? Black Butte Stables offers trail rides through the mountains, perfect for riders of all levels and ages.

Oregon's Beauty Is Endless

There is so much to explore in Oregon, and these eight towns are just the beginning. The state’s natural diversity is incredible, ranging from thriving, biodiverse beaches to alpine lakes and open prairies. In fact, it is very likely that you have a town or two of your own that you would include on this list! As you begin your adventure, you will quickly discover that no matter how many towns you visit, there is always more of the Beaver State to uncover.