7 Ideal Oregon Destinations for a 3-Day Weekend in 2025

Nicknamed the Beaver State, Oregon has made a big cultural impact on the United States, with cities like Portland being world famous for culture and coffee. Oregon's natural landscape is also impactful with its three mountain ranges and Pacific coastline. Within the Oregon interior, you can find many small towns that can compete with Portland for a great weekend getaway, as these towns offer one of the deepest blue lakes in the world, a haystack rising out of the waves, the largest collection of covered bridges in the West, and scenic cabins and lodges to stay at for a three-day weekend. Here are seven ideal Oregon destinations for a three-day weekend in 2025.

Sisters

Sisters will make you feel like you're in the Old West while still being in a West Coast state. Located in Central Oregon, it's renowned for the Sisters Rodeo, which takes place every summer, and the Sisters Outdoor Quilt Show, which takes place in July. The town is also close to majestic volcanic mountain peaks, which make for great hiking trails like the simpler Sahalie Falls and Koosah Falls Trail or the difficult South Sister Trail, which goes up the tallest of the Three Sisters chain of volcanoes.

Anglers can go to the Metolius River to catch a variety of trout species along with mountain whitefish. While in downtown Sisters, explore some of the many cute shops like Paulina Springs Books or the Swiss-clock shop Beacham's Clock Co. Need a spot to stay? Stay at the picturesque Creekside Campground that's close to downtown.

Klamath Falls

Named after the Klamath people, Klamath Falls is known for having some of the best natural sites in Oregon, such as Crater Lake. This lake is one of the deepest lakes on earth, nestled thousands of feet above sea level in Crater Lake National Park. It sits within a dormant volcano and has some of the purest blue waters, making it truly a sight to behold. The area also has beautiful wildflowers like Balsamroot, Lupine, California Poppies, and more, which are visible on trails like the Klamath Ridgeview Trail.

Klamath Falls has world-class lakes and wildflowers, as well as unique museums, such as the Favell Museum, which houses one of the largest Native and Western art collections, including the Fire Opal arrowhead. For your weekend stay, you can retreat into nature at lakeside lodges like the nearby Lake of the Woods Resort, which is a short drive away. Or, opt for Shilo Inns to stay closer to town.

Jacksonville

Jacksonville is a Gold Rush-era town that sprang up in the 1850s as prospectors moved in to seek their fortune. Today, fortune seekers come here looking for an excellent small-town experience. Jacksonville regularly ranks high on lists of best small towns in America due to its variety of experiences. History buffs can see one of the oldest historic cemeteries in Oregon at the 1860 Jacksonville Cemetery or the 1863 Beekman Bank Museum, the oldest bank in the state.

One of the best ways to see all the historic places in town is to take the Jacksonville Trolley tour through downtown. Jacksonville is also a favorite spot for wine aficionados due to its rich diversity of wineries like Rellik Winery. This spot is unique for the furry alpacas that hang out next to the tasting room. You can book a stay right next to the local wineries at the Wine Country Inn.

Cannon Beach

Cannon Beach is famous for being one of the most beautiful towns in the entire world. That's in no small part due to its most noteworthy landmark: Haystack Rock. It's a basalt sea stack that's 235 feet tall, and can be reached by foot during low tide. It's known to host beautiful sea stars and puffins, making it a dream for nature lovers. Moreover, the rock is located near the scenic Ecola State Park, a beautiful place to bird watch, whale watch, relax by Indian Beach, or catch a glimpse of the Tillamook Rock Lighthouse.

This beautiful landscape inspires a rich art scene, which visitors can experience at one of the many art galleries in town, like the Bronze Coast Gallery. If you'd like to find a place close to Haystack Rock, go to the Hallmark Resort & Spa.

Cottage Grove

This town doesn't just have a cute name; it has an adorable vibe. Founded in 1855, Cottage Grove is noteworthy for being the Covered Bridge Capital of the West. There are six covered bridges in the area, including Chambers Bridge, the only covered railroad bridge west of the Mississippi. One of the most popular ways to see all the bridges is to go on the Cottage Grove Covered Bridge Tour Route, a 20-mile driving and cycling route. There are also two lakes in Cottage Grove: Cottage Grove Lake and Dorena Lake, which are available for swimming, boating, or water skiing. If you're looking for a good place to eat, go to The Axe and Fiddle, a renowned nightlife spot with craft beer and organic food. There are plenty of other attractions in town to explore, which are easily accessible from the Cottage Grove Inn.

Ashland

This mountain town is a must-visit for art and nature lovers alike. Ashland prides itself on offering big-city attractions with a small-town vibe. For example, it's home to the Oregon Shakespeare Festival, which runs from March to October with performances at one of the oldest Elizabethan-style theaters in the country. It also has a world-class art museum, the Schneider Museum of Art, located on the Southern Oregon University campus.

For outdoor exploration, there are many different directions to go. You can go up into the mountains with the Grizzly Peak Trail, which offers a nearly 6,000-foot view of the town below, or you can stay downtown in Lithia Park, home to a Japanese garden, rose garden, and the gentle Ashland Creek. Kick up your feet and relax a while during your weekend stay in Ashland at the Winchester Inn.

Astoria

Founded in 1811, this town isn't just the oldest founded town in Oregon; it's the oldest American settlement west of the Rocky Mountains. Don't let the term city fool you; with around 10,000 residents, it's small but rich in culture. Due to its position on the ocean and by the Columbia River, it has a strong maritime tradition preserved at the Columbia River Maritime Museum. At this spot, you can learn about boating traditions from Native to modern times and even tour boats yourself.

There are also majestic historic places to see in Astoria, like the Flavel House Museum, built in 1885 by Captain George Flavel. It's known for its beautiful woodwork, hardwood fireplace mantels, and Victoria era artifacts. Visitors can walk in the footsteps of the Lewis and Clark Expedition at the Lewis and Clark National Historical Park, featuring a museum and a 6.5-mile Fort to Sea Trail. Speaking of the river, you can stay right on the river at the Astoria Riverwalk Inn.

A Long Weekend In Oregon

These Oregon towns have some of the most beautiful natural wonders on earth, which makes them ideal for spending an entire weekend. After all, it'll take more than one day to see all Klamath Falls has to offer, from Crater Lake to the wildflower trails or to hit the mountain and garden trails of Ashland. For those who aren't outdoorsy, there are plenty of other things to do in these towns, from drinking wine with alpacas in Jacksonville to learning maritime history in Astoria. These seven destinations will make for a perfect three-day weekend.