Upper North Falls in Silver Falls State Park near Silverton, Oregon.

Small Towns In Oregon That Come Alive In The Fall

A state renowned for its local Douglas fir trees, Oregon unfolds its beauty in the form of deserted dunes, charming waterfront towns, and lush forests. Thanks to its diverse landscape, fall is orchestrated with a symphony of Maple, Dogwood, Oak, Birch, Aspen, and Cottonwoods, Oregon encapsulates every one of the bright fall colors one imagines while picturing autumn leaves. While the entire state offers a scenic feast for the eyes, it is in the northwestern towns such as Astoria and Silverton where the foliage truly ignites, making Oregon the perfect escape for leaf-peepers, even those crossing state borders from nearby Washington.


Octagonal red, round, barn on a farm near Joseph, Oregon
Octagonal red, round barn on a farm near Joseph, Oregon.

Opening the ultimate list of small-town fall destinations is Joseph, a nature-centric community that makes almost every list of the most beautiful towns in Oregon. Some have attributed the town’s beauty to its surrounding snow-capped mountains and lush acres of greenery, while others fell in love with the city for being a paradise for adventurists. Sitting at the foothills of the Wallowa Mountains, Joseph, Oregon, is also agriculturally rich and hosts events that support local industries like the Wallowa County Farmers’ Market and Main Street. Better yet, Joseph’s vast lands and remote location away from major cities make up one of the least crowded destinations to catch fall foliage. 


Main Street in Sisters, Oregon
Main Street Sisters, Oregon. Image credit Bob Pool via Shutterstock.

Adding to the list of nature-centric destinations to embrace the colorful fall season is Sisters in Oregon. This small town is home to over 260 mi of hiking trails along with lively community events. The Sisters Fall Street Festival brings out the best of the community with local foods, crafts, arts, and more. Sister’s proximity to the Cascade Mountains makes it an outstanding destination in Oregon. The small town is also located near a range of breathtaking waterfalls that visitors can explore during their stay, like Proxy Falls, which sits 28 mi west on Highway 242, and Obsidian Falls, located in the depths of the town’s nature and can be found through a 12 mi hike of Obsidian Trailhead. Tour the downtown area of Sisters, indulge in wild-west-themed architecture, and enjoy a sense of a tight-knit community of welcoming locals and small family businesses. South Sister Trail, Sahalie Trail in Willamette National Forest, and Tam Mc Arthur Rim Trail located in Deschutes National Forest are three of the best-ranked trails in the area, according to enthusiasts. 


Aerial view of Ashland, Oregon
Aerial view of Ashland, Oregon.

Ashland sits even closer to the Cascade Mountains than Sisters, located on the foothills of the Siskiyou and Cascades ranges. The rugged mountain town offers an abundance of experiences from scenic cruises to harvest season family Halloween-themed activities; Ashland is known for its vast farmlands and vineyards that also add to the mountainous leaf-peeping experience. Endless hiking paths make it one of the best Oregon towns to catch the foliage. However, Lithia Park is a locally renowned go-to destination to embrace the change of season. With Recreational spaces, a Japanese Garde, two duck ponds, and more, Ashland’s central park makes for a perfectly Instagramable trip. Aside from vibrant nature, visitors to Ashland will stay entertained learning about the town’s history in places like the Ashland Library, ScienceWorks Hands-On Museum, and Schneider Museum of Art.


A view from above the Astoria-Megler bridge in Astoria, Oregon.
A view from above the Astoria-Megler bridge in Astoria, Oregon.

Astoria is a waterfront town in the Beaver State connecting Washington to Oregon via the Astoria-Megler Bridge. The waters of the Youngs and Columbia Rivers surround its unique setting. Astoria Riverwalk is a long, walkable 12.8 mi stretch that is locally acclaimed to have some of the best views and sunsets in town. Those seeking a wilderness-focused trip can venture out to Fort Stevens State Park and Ecola State Park for birdwatching, hiking, and more. Its moderately challenging hiking paths cut through colorful forests of salal, trilliums, maple, and tall hemlock trees, with its most popular trail being the Cathedral Tree Trail, a 1.6 mi path leading to the 300-year-old Sitka spruce tree. 


A gravel road travels along side a vineyard in autumn colors covers the Dundee rolling hills in Dundee, Oregon.
Gravel road and vineyard in Dundee. 

Located in The Willamette Valley, where the wine industry dominates, Dundee is best visited for its excellent cuisines, scenic trails, and calm atmosphere. Pack your baskets and handpick some fresh grapes during their harvest season when you visit Dundee; catch sites of extensive yellow acres of vineyards backed by a bouquet of green, orange, and red when you visit Dundee, Oregon, this fall season. The Harvey Creek Loop is among the most popular hiking destinations to witness the foliage for its Douglas-fir, Red Maple, and challenging rock paths. Argyle Winery, Fox Farm Vineyards, and Earth Winery are some of the most famous wineries in the area. 


Two people taking selfie photos in front of South Falls at Silver Falls State Park near Silverton Oregon
Tourists in front of South Falls at Silver Falls State Park near Silverton, Oregon. Image credit Bob Pool via Shutterstock.

Every list of small towns to visit in the fall is complete with Silverton, a historically significant town that was once a hub of the mining industry. Located in Marion County, Silverton was named after the Creek that crosses the city, passing by Coolidge McClaine Park, a perfect family-friendly destination. Yet another town that is in proximity to the Cascades, Silverton sits 14 mi away from the city of Salem in Oregon. Indulge in an array of challenging activities like tree-climbing and hiking at Silver Falls State Park, visit the 40-acre Wooden Shoe Tulip Farm, and don’t miss out on the chance to enhance your nature-focused trip to the Oregon Garden, an 80-acre botanical garden. 


The sun sets in the sea and illuminates Heceta Head Lighthouse, Oregon
The sun sets in the sea and illuminates Heceta Head Lighthouse, Oregon.

Wrapping up and balancing out the list of the best towns to catch the foliage is Florence, a city nicknamed Oregon’s Coastal Playground for its beaches. Florence is one of the state’s best towns that come alive in the fall for its distinctive and diverse settings where visitors can embrace The mix of colorful trees that shed their leaves while enjoying unique activities like sandboarding the town’s dunes and exploring some of the largest Sea caves in America. Heceta Head and Hobbit Trail are among the most scenic spots in Florence, leading hikers from Hobbit Beach to Heceta Head, ending with rewardful cliff-top views of the tree-covered Devil's Elbow and Cape Cove. Explore the Sea Lion Caves, surf the dunes of Jessie M. Honeyman Memorial State Park, and embark on a whale-watching tour to get the most out of your visit to one of the most beautiful small towns in Oregon. 

Finally, the dense forests of Oregon, breathtaking mountainous backdrops, and abundance of activities are what make the Beaver State home to some of the best small towns that come alive in the fall. Choose between different settings and attractions and plan your trip towards a relaxing, challenging, or entertaining fall escape. 

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