For the past year and a half I have been making my way all around Oregon and then back again. My job in Oregon has required a lot of traveling and puts me on the road every week. While that much traveling can get really exhausting, one thing I’ve loved about it is getting to see and experience all the small towns of Oregon that I probably would never see otherwise.
Now, as that chapter in my life comes to an end (more on this later), I am reflecting back on some of my favorite small towns to visit in Oregon. Next time you make a trip to Oregon, I hope you’ll consider visiting one of these hidden gems!
Sisters, Oregon
I immediately fell in love with Sisters, OR the first time I saw it, and it still remains my favorite small town in Oregon. Located in Central Oregon with a population of just over 2,000, Sisters, OR will make you feel like you’ve stepped back in time. It hosts the Sisters’ rodeo during the second week of June every year, is close to a lot of outdoor recreation, and surrounded by ranch land.
What to Do: Walk around the cutest downtown you’ll ever see.
Where to Eat: The Porch
Cannon Beach, Oregon
Cannon Beach is the best town on the Oregon coast, in my opinion. Along the Northern coast of Oregon, with a population of less than 2,000, the downtown area is clean and nice to walk around, with a ton of good restaurants and cute shops to explore. The beach is very large and is famous for Haystack Rock, which you might recognize from a scene in The Goonies movie. Cannon Beach is also very close to Ecola State Park, with gorgeous views of the coastline and mossy forest landscapes.
What to Do: Walk on the beach near Haystack Rock and visit Ecola State Park
Where to Eat: Pelican Brewing and Crepe Neptune for dessert
Hood River, Oregon
A town located right on the Columbia River, Hood River is definitely one of my favorites. A population of about 7,500, there’s tons to do if you like water sports and outdoor activities, and is a huge kite surfing area.
What to Do: Go to the Columbia River Gorge or try kite surfing
Where to Eat: Full Sail Brewing Co.
Pendleton, Oregon
A less frequented area of Northeast Oregon is where you’ll find Pendleton, OR. Known for their wool mills and round-ups, Pendleton, OR has a Native American history. With a population of just under 17,000, Pendleton is the largest city in Eastern Oregon.
What to Do: A visit to Alexander’s Chocolate Classics in downtown Pendleton is a must
Where to Eat: Great Pacific
Sunriver, Oregon
Just South of Bend, OR in Central Oregon, you’ll find the popular vacation destination of Sunriver. It is more of a resort community but has some great amenities, as well as a lot of holiday activities. With a population of less than 2,000, you may not spend too much time in town, but can enjoy all the outdoor recreation around the town, including Mt. Bachelor.
What to Do: In the warmer months, rent bikes and ride around the many paved trails
Where to Eat: Marcello’s Cucina Italiana
McMinnville, Oregon
McMinnville is a little-known Oregon town located in the Willamette Valley and home to many wineries. A population of over 33,000 makes McMinnville a larger town with a small town feel, not too far from the big city of Portland.
What to Do: Visit a winery in the area
Where to Eat: Los Molcajetes
Astoria, Oregon
Located on the North Coast of Oregon, Astoria is a quaint port town with beautiful views of the Columbia River, where the river meets the Pacific Ocean. Astoria has a population of under 10,000.
What to Do: Climb up the Astoria Column for views of the whole town and coast, check out the Cannery Pier
Where to Eat: Bowpicker Fish n Chips, TRUST ME
Ashland, Oregon
A town in Southern Oregon that should definitely make the list is Ashland, OR. With a population of just over 20,000, Ashland is known for it’s big artistic community, with a lot of theater events and performances.
What to Do: Go to a show and visit downtown
Where to Eat: I can’t remember what I’ve eaten here that was good, but leave a comment with your experiences below!
Coos Bay, Oregon
Coos Bay, OR is a coastal town in Southern Oregon that is most famous for being the hometown of Steven Prefontaine. It is one of the largest cities on the Oregon Coast with a population of about 16,000.
What to Do: Drive down Cape Arago Hwy to watch the sunset at Sunset Bay State Park
Where to Eat: EZ Thai Restaurant
Woodburn, Oregon
Ok so I admit that I don’t know much about the actual town of Woodburn, OR, but I know that it is home to the Wooden Shoe Tulip Festival and that is definitely something that can’t be missed! Woodburn is located in the Willamette Valley between Portland and Salem, with a population of about 25,000
What do Do: Visit the Tulip farm in April
Where to Eat: ???
I want to hear from you! Which small Oregon town sounds the most fun to you? What’s your favorite small town in Oregon?
I would so love to visit Oregon again sometime! I went to Ashland back when I was in high school for an AP English field trip (their Shakespeare festival was a lot of fun)!
Yes, there’s definitely lots to explore!