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7 Small Oregon Towns to Explore in 2025
Quintessential Small Towns and Main Streets to Explore in 2025
7 Oregon towns that will make you question the big city life
written by Jean Chen Smith
I am nearing my ten-year anniversary as an Oregonian, and I still feel as though there are pockets of this state to be discovered. Coming from suburban New Jersey and having worked in New York City for almost a twenty-year stretch, I have come to appreciate the small hamlets and communities spread across our great state, which is just a tad bigger than the United Kingdom.
I love the idea of escaping the hustle and bustle of our daily lives for some downtime— that is why small towns are so enticing. They offer history, charm and a laid-back pace of living. There are also plenty of opportunities to connect with nature and wildlife. We have rounded up seven of our favorite idyllic small towns and main streets in the state. Perhaps they are on your list as well. If not, spend a day or a weekend putting that to-do list away and visiting one of these delightful spots.
Jacksonville
Recognized as a National Historic Landmark town, Jacksonville sits in Southern Oregon. With approximately 3,000 residents, it boasts a vibrant downtown with quaint shops, galleries and restaurants. Best known as a Gold Rush throughway, many of the town’s original buildings remain intact, adding to its charm. The Britt Music & Arts Festival, which hosts concerts from June to September, is a huge draw.
Immerse yourself in nature at Forest Park. It spans 1,080 acres, offering more than 30 miles of trails for hiking and exploring. On clear days, you will be able to see the Siskiyou Mountains and the Three Sisters. A thirty-minute drive brings you to the beginning of the Applegate Valley Wine Trail, which features a collection of nineteen wineries to check out. There are five tasting rooms right in town to visit.
Cannon Beach
With about 1,500 year-round residents, Cannon Beach and its adorable main street offer plenty of small-town charm. Book reservations at the newly remodeled Surfsand Resort. Rooms are spacious and bright, featuring flat-screen TVs, digital fireplaces and luxurious bathrooms, with some suites offering soaking tubs.
Borrow cruiser bikes from the front desk to explore the downtown, which is lined with boutiques and restaurants. Visit Fetch to pick up some treats and toys for your pup. B.Boutique is owned by a mother-daughter team, Emily and Jenny, who welcome guests into their shop with enthusiasm, ready to style and dress them. I love independent bookstores, and Cannon Beach Book Company is definitely worth a stop—it has been open for thirty years and carries a good selection of new and older books, for readers of all ages.
Make reservations at Wayfarer for dinner, where you will be delighted with its many seafood options. Order a pint and splurge on the crab bake—it is a local favorite. Afterward, head down to the beach and settle into comfortable chairs as your hotel attendant prepares a bonfire for you. The cost is $50 and reservations need to be booked in advance, but it is well worth the sunset views.
Bandon
Another charming coastal town, Bandon sits at the southern tip of the state, about two hours from Crescent City, California. Named by George Bennett, one of the original settlers in the late 1800s, this is your classic beach town, with spectacular beaches, charming hotels and a historic lighthouse. The Old Town District is where you will find charming shops, a diverse offering of restaurants and a nice collection of art galleries.
Alloro Wine Bar & Restaurant offers regional Italian fare along with an impressive wine list. The Loft Restaurant and Bar serves breakfast and lunch. It is a local favorite serving nice-sized portions with a friendly smile. You can not go wrong with the crab cake Benedict—it is made in-house and comes with a healthy side of sautéed spinach. For lunch, you will find hearty salads and a variety of sandwich and burger options that are sure to satisfy.
Make sure to visit Bullards Beach State Park to view the sand dunes for which the area is known. It is a dramatic and impressive sight—even more so if you rent a dune buggy and go out for a spin. For those who want to learn about the town’s past, head over to the Bandon Historical Society Museum, where you will find informative exhibits and artifacts. Make your way to the Coquille River Lighthouse, the very last lighthouse built in Oregon. It guided mariners from 1896 through 1939.
Carlton
McMinnville often gets recognized in the Willamette Valley for having a thriving downtown while neighboring Carlton gets overlooked. However, the small community of 2,300 has lots to offer. With more than twenty tasting rooms, boutiques and a solid restaurant scene, visitors can look forward to a bevy of different experiences within a compact radius. For enchanting accommodations, rest your head at Abbey Road Farm. Rooms are set inside three converted grain silos, offering luxe linens, plush beds and pastoral views. The 82-acre working farm produces small-batch bottles of pinot noir, chardonnay and sparkling rosé. A hearty homemade breakfast is included with your stay.
Stroll through the idyllic main street and drop into Milltown Mercantile, which houses arts and gifts made by local artisans. You will find everything from clothing and accessories to soaps and home goods. At Park & Main, grab a table and order a wood-fired pizza (they have twelve options!) and the roasted beet salad. Ingredients are fresh and the atmosphere is casual and friendly. Besides wine tasting and shopping, you can enjoy the tranquility of nature at Our Lady of Guadalupe Trappist Abbey’s Forest Trails. The monastery sits on 1,300 acres and welcomes all visitors to enjoy its forested paths for quiet contemplation.
Independence
Set along the Willamette River, Independence is an ideal destination for foodies and antique-lovers. You will find the main street dotted with Victorian-era towers and brick buildings dating back to the late 1800s. From the 1890s to the 1940s, the town was the epicenter for a booming hops industry and a hub for boat trade on the Willamette River. Today you will find eclectic restaurants such as Jubilee Champagne and Dessert Bar, The Inferno and Gilgamesh Brewing’s The River to satisfy diverse palettes.
The Collection on Main houses a treasure trove of vintage furniture and antiques, along with new home decor and clothing items. Also nearby is The Hidden Collection, which has more than 4,000 square feet of antiques and collectibles.
Stay at The Independence Hotel, a boutique property that offers spacious accommodations, complimentary breakfast and on-site dining. Territory restaurant offers a vibrant dinner menu, using fresh and local ingredients whenever possible. When the weather is agreeable, ask for an outside table overlooking the river. Visit Independence Riverview Park, which snakes along the Willamette River and offers picturesque views and walking trails.
Cottage Grove
“Small town, big heart.” That is Cottage Grove’s motto. Known as the Covered Bridge Capital of Oregon, you will find six covered bridges in this small neighborhood, covering approximately 3.89 square miles. The oldest of them, Chambers Railroad Covered Bridge, dates back to 1925, making it 100 years old. The Covered Bridges Scenic Bikeway is a 35.8-mile loop that takes you through part of the historic downtown, following the Row River, on a tour of covered bridges. The route is mostly flat and with minimal exposure to traffic.
Founded in 1888, the Historic District features buildings originally designed by notable architect John Hunzicker, who designed Eugene’s Armory. It is where you will find specialty shops, antiques and delightful restaurants, such as Urban Kitchen and The Axe and Fiddle.
The town of less than 11,000 residents hosts many fun events year-round, including the annual Half Marathon and 10K, the Antique Aircraft Fly-In and the Rock, Roll n’ Rumble.
Joseph
Nestled at the base of the Wallowa Mountains in Eastern Oregon, Joseph is the quintessential small town with 1,200 residents and a bustling main street full of small shops, galleries and cozy eateries.
There are many options when it comes to outdoor activities. Hike to the BC Falls Overlook via the Wallowa Lake Trailhead where you can see the falls and have a nice view of Wallowa Lake. The Zumwalt Prairie is a pristine, 329,600-acre landscape that features meadows, rolling hills and colorful wildflowers when in season (from mid-April to late June). To explore Wallowa Lake up close, consider renting a kayak or paddleboard at JO Paddle. The Josephy Center for Arts and Culture offers workshops and classes, in addition to an ever-changing assortment of exhibits.
The conveniently located Kokanee Inn has modern and minimalist rooms and suites. The Sierra Suite is its largest accommodation, sleeping up to seven people, with a cozy sitting area.
Head over to the Stubborn Mule Saloon & Steakhouse for some casual fare. Or try The Dog Spot, a small café that serves scratch-made fare with a menu that changes weekly. They also have an outdoor seating area for you and your pups.
