7 Best Towns In Oregon For A Two-Day Recharge

The end-of-summer blues may be creeping in, but that does not mean it is too late to travel and make the most of your surroundings. And for Oregon residents, a quick weekend trip has never been easier. Whether you live in Portland, Salem, or elsewhere in the state, there are plenty of towns worth exploring. These seven destinations offer the perfect weekend escape, with waterfalls, wineries, river gorges, and coastal trails that will help you make the most of the fall season this year.

Silverton

Located in the heart of the Willamette Valley, Silverton is less than an hour from Portland and just 30 minutes from Salem, making it a convenient weekend destination for those hailing from the city. As you might expect in a Willamette Valley town, vineyards are plentiful. Paradis Vineyards, founded in 2017 by two fourth-generation farmers, has a new tasting room with beautiful views of the valley, perfect for sipping a glass of wine. Want to spend the weekend outdoors? Silver Falls State Park is just a short drive from town as well, home to a massive, 177-foot cascade that travelers can reach via a nationally recognized hiking trail. To tie it all together, reserve your stay at the Oregon Garden Resort, directly connected to the iconic 80-acre botanical garden filled with diverse plant life.

Hood River

Located at the intersection between the Columbia River Gorge and the Cascades, the scenery in Hood River is unlike any other in Oregon. It is also just a short drive away from Portland, making it another great spot for a quick weekend trip. Windsurfing is one of the town’s most popular activities, with several outfitters offering rentals and lessons. Brian's Kiteboarding, Wing Foil, Windsurf & Stand up Paddling is a great option if you are looking for some guidance, with the school offering lessons for kiteboarders and windsurfers for all levels. Another great way to see the gorge is on a bike tour! Sol Rides offers e-bike tours through the gorge and Hood River Valley, passing wineries, orchards, and other landmarks. If you are looking for a charming and local place to stay during your getaway, consider staying at The Inn at the Gorge, a historic inn with six guest rooms, a terrace, wrap-around porch, private backyard, and other amenities to help you relax.

Florence

If you are seeking an adventure-filled weekend, you are just about guaranteed to find it in Florence. This coastal town lies on the edge of the Oregon Dunes National Recreation Area, the largest coastal dunes in North America. The area, which stretches around 40 miles in total, is home to dunes that reach up to 500 feet in height, which visitors can explore on a horseback riding excursion or buggy tour with a local outfitter. The Sea Lion Caves are another one of the town’s most notable attractions, featuring a naturally formed basalt rock sea cave, filled with hundreds of sea lions! As evening falls, continue the adventure with a stay at the Heceta Lighthouse Bed & Breakfast, housed in a historic keeper’s home dating back to 1894 and among the few remaining lightkeepers’ cottages on the Pacific Coast.

Baker City

Located along the Oregon Trail, Baker City is chock-full of western history. Travelers can dive into the trail’s history at the National Historic Oregon Trail Interpretive Center, an interactive museum and outdoor area that exhibits what pioneer life was like for those who once passed through. The Geiser Grand Hotel is another prominent historic landmark, first established in 1889 and featuring crystal chandeliers and ornate mahogany in every room. Grab a drink at Barley Brown's Brew Pub before leaving town, a family-owned brewery that has won numerous awards for its brews over the years. A few of the beers you might be able to try include golden ales, Irish stouts, and smoked-rye bocks, among several others.

Sisters

Home to roughly 3,700 residents and sitting at the foot of the Cascades, Sisters provides travelers with a complete change of pace for the weekend. There are plenty of hiking trails in the surrounding areas, such as the Whychus Creek Overlook, which is just 10 minutes from town and offers panoramic views of the Three Sisters’ Peaks and the Whychus Creek Wild and Scenic River area. The tight-knit community hosts events and markets throughout the year, such as the Sisters’ Farmers Market, which travelers can visit on Sundays between June and October each year. Conclude your laid-back day with a stay at the FivePine & Cabins, which sits among a vast pine forest with eight lodge suites and 36 craftsman-style cabins.

Yachats

Often referred to as the “Gem of the Oregon Coast,” Yachats has scenic trails, sandy beaches, and cozy inns for a memorable weekend on the coast. If you are craving a day outdoors, consider a hike on the 804 Trail, which extends along coastal bluffs and tide pools, providing unbeatable views of the Pacific and even the occasional whale sighting. Thor’s Well is another worthwhile natural attraction, a dramatic sinkhole where seawater seems to vanish into a bottomless hole in the ocean. For ocean views right from your room, consider staying at The Drift Inn, which offers both sea-facing accommodations and dog-friendly options for those traveling with their furry companions.

Jacksonville

Set in the Rogue Valley, Jacksonville complements its gold rush history with a relaxed wine scene. History lovers can hop aboard the Narrated History Trolley Tour, a 45-minute ride that passes commercial buildings, vintage homes, and other landmarks that shaped the town. Several hotels and inns provide historic experiences as well, such as the Magnolia Hotel, which was built in 1928, before being converted into a bed and breakfast in 2007. Those interested in the area’s wine scene can enjoy a tasting at Red Lily Vineyards, a family-owned and operated vineyard that has been part of the community for over 20 years.

Final Thoughts

You are never far from something beautiful in Oregon. With just a weekend away, you can create some remarkable memories. Towns like Florence and Yachats promise a relaxing and scenic weekend on the beach, while other towns, like Hood River and Sisters, are filled with hiking and water recreation opportunities. Wineries are easy to find along the way, too! So make the most of every day and enjoy a couple of days off exploring these seven towns.