I am a sucker for small towns — the hand-painted signs, family-owned businesses and how a quick stroll reveals the distinct character of each. That’s one reason I love exploring the Willamette Valley, which so many people only get to see passing by at a blurry 65 miles an hour.
Here in Oregon, Interstate 5 is most graciously known as the thoroughfare threading through some of our major cities. Yes, it’s a perfectly zippy path I’ve taken to get from place to place. But you don’t get a sense of the valley’s true charm until you slow down, pull off the main drag and ease into the rhythm of its historic small towns, each with its own sense of place and plenty of local favorites to uncover.
Pull a few pages out of my travel journal and plot your own laid-back getaway to the cutest and most compelling towns in the valley — a sweet region originally home to the Ahantchuyuk, Cow Creek Umpqua, Kalapuya, Siuslaw, Tsankupi, Yamhill and Yoncalla tribes.
Like several other Oregon towns, Dayton was given its name as a tribute to one of its founders’ home towns (you guessed it — the one in Ohio). Come to this proud agricultural community with an appetite, as the star is its food-and-wine scene. Start at The Block House, a cafe occupying an 1880s-era church, where top treats on the menu include pillowy cinnamon roll pancakes and deep-fried pickles with kickin’ sauce (a delicious, zesty concoction of more than 20 ingredients). Stroll through the Courthouse Square Park and stock up on snacks like cacahuates japoneses and saladitos at the local Zu Kaza Mexican market across the street.
Fuel up on wood-fired bread and happy dance-worthy dishes at Red Hills Market, and browse their well-curated shop of locally made goods, including more than 50 varieties of local and imported cheeses. Take several hours to soak in the sights at Red Ridge Farms for double-duty tastings at Durant Vineyards and the adjoining Durant Olive Mill, where you can enjoy the Pacific Northwest’s first commercial olive mill along with flights of estate wines on the same farm. Each fall, Red Ridge hosts the Olio Nuovo Festival, which marks the olive harvest.
Tuck in for the night at The Vintages Trailer Resort, a cool base camp for your small-town touring, which pairs colorfully restored trailers with hotel-grade amenities such as a pool, terry-cloth robes and Adirondack outdoor seating areas.
The Bavarian-inspired town of Mt. Angel was incorporated in 1893 after a Swiss Benedictine monk chose this site as the perfect home for an American abbey. Around the same time, an influx of Bavarian immigrants settled, and the two cultures coalesced to rouse the half-timbered façades and “Willkommen” signs, which remain today.
Start your morning sipping a latte and perusing locally made and vintage wares at Old Stone Coffee & Collectibles. Chow down on currywurst and crisp shoestring fries with a side of spaetzle at Mt. Angel Sausage Company before exploring the impressive Mount Angel Abbey grounds. Must-see stops include the library (designed by renowned Finnish architect Alvar Aalto), the coffee and gift shop (pick up spicy pretzels and cookies), and heavenly pairings of brews and smoky Lonely Lane Farms beef jerky at the on-site Benedictine Brewery.
Stop by The Glockenspiel Restaurant and Pub for dinner and a show; order the fondue to share, and plan your visit around the 49-foot clock tower (the tallest in the United States), which has daily performances at 11 a.m., 1 p.m., 4 p.m. and 7 p.m. End with a nightcap at Bierhaus. Still craving more German-fueled fun? Join over 300,000 attendees at Mt. Angel’s beloved Oktoberfest, held over a weekend in September every year since 1965.
Lush scenery and a world-class garden earn this small town the nickname of “Oregon’s Garden City.” The perfect stopover begins with a cup of joe at Silverton Coffee Station and plenty of snacks for the trek to Silver Falls State Park. Hike a 7.2-mile loop to see a series of waterfalls on the gobsmacking Trail of Ten Falls, or walk about 15 minutes onto the trail to sneak a peek at the iconic South Falls. If you prefer to travel by bike or horseback, the park’s expansive system of backcountry trails offers both.
Silverton’s compact downtown could arguably be the state’s cutest. Stop into Creekside Grill for a balcony-side meal overlooking the photogenic Silver Creek. Spend an afternoon popping into family-owned businesses housed in historic buildings, and check out the town’s nearly two dozen murals. Have a local ale at Silver Falls Brewery before a movie at the vintage Palace Theatre.
Stay at the Oregon Garden Resort for many reasons, including an early-morning stroll through their gardens, stretching over 80 acres, before it opens to the public. Don’t miss architectural highlight The Gordon House for a guided tour of Oregon’s only building designed by Frank Lloyd Wright.
The idealized vision of Main Street America is, without doubt, Cottage Grove’s very own downtown, complete with white-picket fences, warm brick buildings and plentiful historic markers. Need I mention its twice received the All-American City Award? You get the picture. Known as the “Covered Bridge Capital of the West,” this twee town is also surrounded by old-time views perfect for sightseeing along the Cottage Grove Covered Bridge Tour Route and the Covered Bridges Scenic Bikeway.
Community-led efforts to preserve the town’s history are evident everywhere you look. Pick up some radical literature at The Bookmine bookstore; learn about the late writer Opal Whiteley, the subject of a nearby mural; and rent some wheels from Rainy Peak Bicycles to explore the surrounding countryside by bike. Walk right up to the kitchen window to order up an old-fashioned chocolate-malt milkshake and burger at Bonanza Drive-Up. This Americana vibe continues at Cottage Grove’s quintessential hotel: The Village Green, a slice of roadside charm that was built in 1960 as one of the state’s most luxurious motor resorts.
Escape into nature at the idyllic Dorena Lake, with bicycle and hiking trails, boating, campgrounds, and picture-perfect picnic spots. Have a drink and catch a show at Axe & Fiddle Public House back on Main Street for the evening, or check out their drag brunch, hosted every fourth Sunday.
Conclude a jam-packed itinerary by bowing out with the smallest of these small towns. Home to just shy of 2,000 residents, Brownsville has a local go-to for all the important things in life — such as the best pastries (Randy’s Main Street Coffee) and the best vino (Harpers Wine House). To get a sense of the town’s past, call ahead to visit the Moyer House, a gloriously resorted Italianate villa-style home circa 1881, for a personable tour detailing the renovation work and story of the original homeowners, John and Elizabeth Moyer.
Take a literal walk down memory lane at the Linn County Historical Museum, which offers an impressive installation of replica storefronts where you can pop into what resemble old shops such as a pharmacy and blacksmithing station. Throughout the museum, informational plaques detail each site’s significance and prominent members of society — seemingly free of whitewashing the town’s history, with passing mentions of Black and indigenous residents. You can even dress up in your best pioneer-era digs while pretending to hitch your wagon on the Oregon Trail, and you may simultaneously feel tempted to develop a wardrobe exclusively comprised of floral-patterned muumuus. On the way out, pick up a self-guided walking-tour map of “Stand By Me” filming sites, an official stop on the Historic Oregon Film Trail, and buy some memorabilia (I snagged a commemorative “Stand By Me” Day comb!) as a keepsake.