Right in the heart of the United States’ Pacific Northwest, Oregon has it all: mountains and a gorgeous Pacific Ocean coastline, coupled with sophistication and culture in Portland and charming, relaxed town life in the colorful and friendly towns that dot the coast and interior. A haven for outdoor enthusiasts and foodies alike, Oregon never ceases to impress with its arts scene, nature or microbrewery industry. Get off the highway and explore the small town charm entirely unique to this part of the country.
Lets explore the best towns to visit in Oregon:
1. Ashland, Oregon
Ashland is a picturesque town in the Rogue Valley (what a great name!) right across from the California border. Originally inhabited by the Shasta people, Hudson Bay Company trappers discovered it when passing through via the Siskiyou Trail. Later, the Rogue Valley was settled thanks to the Donation Land Act. Ashland survives the Rogue River Wars clashes between settlers and the Native Americans, and thrives today as a relaxed artsy community.
Make some time to experience town life and enjoy the peace and quiet of the Rogue Valley. While here, browse the many galleries and shops that Ashland is so famous for, such as Gathering Glass Studio or Illahe Studios and Gallery. The Oregon Shakespeare Festival is also hosted in town and is a very popular local festival. Pamper yourself at the Blue Giraffe Spa or enjoy a tasting at the Grizzly Peak Winery. Ashland Creek Inn is nearby and is a perfect place to spend a few nights and relax while staying in Ashland.
2. Astoria, Oregon
Right at the mouth of the Columbia River you’ll find Astoria, the county seat of Clatsop County. John Astor of the American Fur Company founded Fort Astoria, and the town was subsequently formed around this and named after him. Lewis and Clark even spent some time at Fort Clatsop, just south of modern day Astoria.
Come to Astoria to retrace the steps through history of the exploration of the Pacific Northwest. You can spend some time at the Lewis and Clark National and State Historic Parks or the Heritage Museum. Hike up to Young River Falls and be sure to bring your camera! Stop in for a glass at Pilot House Distilling or check in at Cannery Pier Hotel and enjoy its stunning views of the Columbia River. Enjoy the solitude and let the closeness to nature give you a much needed break from city noise and life.
3. Klamath Falls, Oregon
Klamath Falls is located in Klamath County and was originally called Linkville, after the nearby Link River. The region had been previously inhabited by the Klamath and Modoc Native American tribes for several thousand years before the Europeans arrived. Following their arrival, the Klamath Basin became part of the Oregon Trail.
The town is nestled in some gorgeous nature – take a hike out on the OC&E Woods Line State Trail or along the Link River. Take a boat out on the lake or put on your walking shoes and explore the Sky Lakes Trail. Enjoy a delicious meal at Rooster’s Steak and Chop House, or have a drink at the Creamery Brew Pub & Grill. You’ll want to extend your stay and check in to Thompson’s Bed and Breakfast.
4. Baker City, Oregon
Baker City is the county seat of Baker County and named after Edward Baker, known for being the only US Senator ever killed in military combat. He perished while leading a Union charge at the battle of Ball’s Bluff during the Civil War. Despite that depressing fact, the town thrived once the railroad arrived and continues to draw visitors to this day.
Stopover in Baker City and learn about the Oregon Trail at the National Historic Oregon Trail Interpretive Center, or take the Fall Colors Tour at the Baker Heritage Museum if you’re there in the fall. Visit the Sumpter Valley Railway or have a pint at the Baker City Brewing Company. Enjoy the yummy beer this town has to offer: you can even compare brews from the local pubs like Idle Hour Tavern and Barley Brown’s Brew Pub to determine who has the best pint! You can always sleep it off at A Beaten Path Bed and Breakfast before continuing on your way responsibly the next day.
5. Brownsville, Oregon
Brownsville is a town in Linn County, and was formerly named Calapooya after the Kalapuya Native Americans from that region. Set along the Calapooia River, the local Spaulding School was the first original county courthouse in Linn County. Now, the town enjoys fame from being the shooting location for the popular film, Stand by Me, and even has a local day dedicated to it – July 23.
Come out here for a perfection opportunity to disconnect and enjoy reconnecting with nature. Whether you’re out in the backwoods exploring like the heroes of Stand by Me or in town, you’ll find plenty of ways to occupy yourself. Enjoy a selection of local wines at Harpers Wine House or have a drink at Brownsville Saloon and enjoy your time off.
6. Cottage Grove, Oregon
Cottage Grove is located in Lane County, right off Interstate 5. Home to a station for the Southern Pacific Railroad in the 1870s, the town was split over a few colorful local disputes regarding locations of the post office and naming conventions of Cottage Grove vs. Lemati (A Chinook word for mountain). Finally, peace was restored to the region and the split towns consolidated to all be named “Cottage Grove”.
The town retains this unique character and culture- it is known as the “Covered Bridge Capital” of Oregon since it has six covered bridges and has dedicated a festival to them! One bridge in particular, the Chambers Railroad Bridge, is famous for being the only existing covered railroad bridge west of the Mississippi River. You can also attend the Bohemia Mining Days festival or tour the local murals located throughout downtown. Relax at Village Green Resorts and treat yourself to some time away from the city.
7. Florence, Oregon
While not the same as the lovely Italian city that shares its name, Florence, located in Lane County, is not without its own charm. Boasting a beautiful coastline along the Pacific Ocean and on the banks of the Siuslaw River, the origin of the town name is still disputed by locals – some say the town was named after a senator, A. Florence, and others say it was named after a French vessel that shipwrecked at the mouth of the Siuslaw
Leaving the origin of its name aside, Florence is a perfect place to get off the highway and breathe in some fresh ocean air. Explore the Sea Lion Caves, a sea cave that is home all year around to Steller Sea Lions. Also don’t miss the Rhododendron Festival Florence, a festival famous since 1908. Walk out to the Heceta Head Lighthouse or across the historic Siuslaw River Bridge, or follow Frodo along the Hobbit Trail! If you’re up for a challenge, head over to the John Dellenback Dunes Trail and remember to bring your camera to capture the views.
8. Hood River, Oregon
Hood River is a port town on the Columbia River, but is actually named after the nearby Hood River. This town was established in the late 1800s and is in the heart of the Columbia River Gorge. A true nature paradise, the town has a moderate climate, experiencing less rain than in other areas of Oregon.
Check out the Columbia River Gorge while you are here, and drive out to Mount Hood – the views are spectacular. Have a glass (or two!) at Marchesi Vineyards, or if you’re feeling slightly more adventurous, try the wine at the Naked Winery. If you’re a beer lover, the Full Sail Brewing Company tour might be just the thing for you! Eat, drink and be merry at Solstice Wood Fire Cafe & Bar before retiring for the night at the historic Columbia Gorge Hotel.
9. Jacksonville, Oregon
Jacksonville is located just west of Medford, in Jackson County. It is named after the creek that runs through the town, Jackson Creek. It was also one of the first gold claims in the area, and now the Jacksonville Historic District is designated a National Historic Landmark. The town grew up around the gold rush and was home to Oregon’s first Chinatown when immigrants from San Francisco journeyed north and settled here.
Come visit Jacksonville today and you’ll feel like you walked right back into the 19th century – many of the buildings have been nicely preserved and await your exploration. Wander and shop at Jacksonville Mercantile, or appreciate its quirky buildings and old-time phone booths that dot the town. Check in at the Touvelle House Bed and Breakfast and prepare to relax and be merry. There are also many delicious restaurants awaiting your exploration. We recommend the Mustard Seed Cafe or Deja Vu Bistro.
10. Joseph, Oregon
Located in Wallowa County, Joseph was named after Chief Joseph of the Nez Perce people. Founded in 1883, the community was based primarily in agriculture and stock. The railroad brought more business and lumber mills to Joseph in the early 1900s, but now the town relies more on bronze foundries and tourism.
Come visit this town and check out the Chief Joseph Days Rodeo in July, or Bronze Blues and Brews in August. Also in keeping true with the regional reputation of “Oregon’s Little Switzerland”, they hold a Swiss-Bavarian festival resembling an Oktoberfest, but with yodeling and alphorn! You should also explore the gorgeous nature around Wallowa Lake State Park or take the tram up to enjoy the view. Put your feet up at Bronze Antler Bed & Breakfast and enjoy this retreat back to nature.
11. Sisters, Oregon
Located in Deschutes County, Sisters was originally called Camp Polk and was a military post in the late 1800s. Established to address violence in the area resulting from western settlers clashing with the Native Americans, troops were stationed here briefly until they determined that the threat was over. The name was changed to Sisters at this point after the Three Sisters Mountains that bordered it on the west.
Come to this relaxed town and explore the beautiful nature that surrounds it. Hike the McKenzie Pass or up to Sahalie and Koosah Falls. Kayak on Clear Lake or ski at Hoodoo Ski Area in the winter! You can also stay in town and pamper yourself at Shibui Spa. Unwind at Five Pine Lodge and Spa and enjoy a cup of coffee at Sisters Coffee Company!
12. Yachats, Oregon
Yachats is a small coastal town in Lincoln County. Inhabited for 1500 years by Native Americans before white settlers arrived, Yachats is rich in history and archeological remains from those ethnic groups. The indigenous community that resided there once the settlers arrived were forcibly relocated by the army to make space for settlers at Coos Bay, and there is trail dedicated outside of town called Amanda’s Trail, after a blind Native American woman who was a part of this forced relocation.
While this sad history is long behind them, you should take some time to walk along Amanda’s Trail or visit the Little Log Church Museum. You can also enjoy the great views along Yachats coastline or visit Yachats State Park. Walk across the North Fork Yachats Covered Bridge and don’t forget your camera. Unwind at the Wine Place and treat yourself to some luxurious comfort at Overleaf Lodge and Spa, or some delicious seafood at Luna Sea Fish House.
13. Newport, Oregon
Newport is located in Lincoln County, and literally is right on 101 – the highway runs through town. A coastal town that was established in 1882, Newport is the base for National Oceanic Atmospheric Administration research ships and the Hatfield Marine Science Center. Come visit if you’re an ocean enthusiast or just want to hear the sound of the waves crashing into the Pacific Ocean shoreline.
Explore Yaquina Head Outstanding Natural Area – the tide pools are worth some of your time. You can also be a marine biologist for a day as you wander Hatfield Marine Science Center or the Oregon Coast Aquarium! Spend some time at the Newport Historic Bayfront and have some great seafood at Local Ocean’s Seafoods. Watch the sunset from your room at Hallmark Resort and recharge for a few days.
14. Cannon Beach, Oregon
Cannon Beach is located in Clatsop County. William Clark was the first American to reach this area, and was one of the leaders of the Lewis and Clark Expedition. He was exploring during the winter the group passed at Fort Clatsop and came to a viewpoint now called “Clark’s Point of View” to see a “boundless ocean”. That spot is now Cannon Beach, and is the site where Clark and Sacagawea bartered for whale blubber from the native Tillamook people.
If you visit Cannon Beach now, you can see a wooden whale sculpture that commemorates the trade between the Tillamook and Clark. Also, if you stop by in June, you might be in time to compete in their sand-castle building contest! Tour the galleries in town or walk out to Haystack Rock and visit the Oregon Islands National Wildlife Refuge. Taste the rum at Cannon Beach Distillery and continue relaxing at Stephanie Inn. You’ll find yourself just as enchanted as Clark was when he first arrived.
15. Tillamook, Oregon
Tillamook is the county seat of Tillamook County, and located on Tillamook Bay. Named after the Tillamook people, who were the original inhabitants of the area, the town established itself with its dairy farms and cattle. If the name sounds familiar, you’re thinking of Tillamook cheese and their delicious dairy products that helped make the town famous!
Visit the Tillamook Cheese Factory and enjoy the taste-testing! You can sleep off the food coma at Cape Lookout State Park’s beaches or walk it off at the Wildlife Refuge at Cape Meares Lighthouse. Don’t miss the Munson Creek Falls. You can always rest and relax over a drink at Pelican Brewery & Tap Room once you’re back in town, or have a delicious meal at Old Oregon Smokehouse. Stay a few nights and relax at the Ashley Inn of Tillamook.