6 Standout Main Streets In Oregon
Oregon, located in the Pacific Northwest, is a state of diverse landscapes, from the rugged coastline along the Pacific Ocean to the volcanic peaks of the Cascade Range. Its northern boundary is largely defined by the Columbia River with Washington, while the Snake River forms much of its eastern border with Idaho.
While Portland, Oregon’s largest city with a population of over 650,000, is known for its vibrant arts scene, craft breweries, and quirky culture, the state is also home to smaller towns and cities whose downtown streets capture an energetic atmosphere all their own. From historic downtowns to boutique-lined avenues, these main streets offer a closer look at the character, culture, and community that make Oregon stand out.
McMinnville
Located in Oregon’s Willamette Valley in Yamhill County, McMinnville, home to about 35,000 residents, combines small-town charm with a strong sense of community and serves as a hub of Oregon wine country, with vineyards and tasting rooms throughout the region. Downtown McMinnville, centered around Third Street, features McMenamins Hotel Oregon, a four-story historic property with the popular Cellar Bar and Rooftop Bar.
A few blocks away on Park Drive, City Park, McMinnville’s first public park, established in 1906, offers a playground, picnic pavilions, walking paths, and historic markers detailing the area's early beginnings. Annual events hosted downtown range from the UFO Festival each spring to the Santa Parade & Tree Lighting in winter, as well as the McMinnville Farmers Market, which brings together fresh produce, handmade goods, and local treats.
Ashland
Nestled within the Siskiyou and Cascade ranges in Jackson County, just north of the California border, Ashland, with a population of roughly 21,000, has a downtown that is lively and walkable, offering a mix of culture, shopping, and entertainment. The community is also home to Southern Oregon University and the Oregon Shakespeare Festival. On Main Street, movie lovers can catch independent films, foreign features, and documentaries at the Varsity Theatre, while bibliophiles can browse an extensive selection of titles at Bloomsbury Books. For a bit of retail therapy, downtown is filled with inviting boutiques and specialty shops, including Sunday Afternoons Retail Store, renowned for its stylish hats and accessories.
In the heart of it all is the historic Ashland Springs Hotel. Built in 1925, the hotel blends traditional decor with European flair and modern amenities for a comfortable and convenient stay. Just a short walk from downtown, Lithia Park is a great place to enjoy the outdoors. The 93-acre park along Ashland Creek features two ponds, a Japanese garden, sports courts, public greens, picnic areas, a bandshell for outdoor performances, and several miles of hiking trails.
Pendleton
In the heart of Umatilla County, Pendleton, home to about 17,000 residents, offers a mix of Old West charm and modern attractions. Its downtown features landmarks like the Rainbow Café, established in 1883 on Main Street and considered Oregon’s oldest continuously operating tavern, famous for St. Patrick’s Day celebrations. A short walk away on Court Avenue is a hub of family-owned businesses, including Hamley Café & Wine Bar, the Hamley Western Store & Saddle Shop, and the Hamley Steakhouse & Saloon, where visitors can dine, shop, and enjoy drinks within steps of each other.
Just down the way on Frazer Avenue is the Heritage Station Museum, housed in the historic 1909 Pendleton Train Depot. Managed by the Umatilla County Historical Society, the museum features two galleries on regional and local history, along with a schoolhouse, family cabin, caboose, barn, and signal house. Beyond its must-visit local spots, downtown Pendleton comes alive year-round with street festivals, summer concerts, and a festive holiday lights parade that brings the community and visitors together.
Sisters
Located at the foot of the Cascade Range in Deschutes County, just northwest of Bend, Sisters is a small town of around 3,000 residents that stands out for its Old West-style downtown and cozy small-town atmosphere. Along Cascade Avenue is Sisters Saloon & Ranch Grill. Built in 1912 as the Hotel Sisters, the restaurant and bar have been restored, keeping its rustic character while offering burgers, steaks, drinks, and live entertainment.
Downtown also features public artwork, including the iconic stallion sculpture near Larch Street, while nearby Barclay Park showcases murals, such as the Greetings From Sisters piece, reflecting the surrounding ponderosa forests and mountains. For accommodations in the area, options range from the Ski Inn Taphouse and Hotel, a boutique property with wraparound patio views on Cascade Avenue, to the charming Sisters Bunkhouse on Oak Street. Throughout the year, the town hosts weekly gatherings, monthly events, and annual celebrations such as the Sisters Folk Festival and Sisters Outdoor Quilt Show.
Forest Grove
Forest Grove, in Washington County, about 25 miles west of Portland in the Tualatin Valley, is home to roughly 27,000 residents and is anchored by its historic downtown at Pacific Avenue and Main Street, listed on the National Register of Historic Places. The area features Pacific University, whose Old College Hall, the oldest educational building west of the Mississippi River, now serves as the university’s museum. Near the campus, numerous galleries, including Valley Art on Main Street, showcase local artists working in mediums ranging from fiberglass artwork to oil painting. The gallery also hosts classes for anyone looking to explore their creative side.
A few doors down, Guidetti’s Marketplace offers wine, coffee, and gelato in an Italian-inspired setting, with special events, workshops, and private cooking classes, making it a charming stop for visitors. Along Pacific Avenue, McMenamins Grand Lodge provides an inviting place to stay, with multiple guestroom options, on-site dining, bars, and a full-service spa. In the summer, the lodge's outdoor concert series, Concerts in the Grove, adds a lively touch to the downtown experience.
Astoria
Perched at the mouth of the Columbia River, Astoria, home to about 10,000 residents, is Oregon’s oldest town and the first permanent US settlement west of the Rocky Mountains. A main attraction near downtown is the Astoria Riverfront, where a trail follows part of the historic Astoria & Columbia River Railroad. Visitors can also hop on the trolley that runs along the old freight tracks for a guided tour of the waterfront. While there, take in the views of Youngs Bay and the Astoria-Megler Bridge, access shops and restaurants, and stop at historic sites like the Maritime Memorial and the Columbia River Maritime Museum.
A short drive brings you to Commercial Street between 12th and 14th Streets, the heart of downtown. For entertainment, the Liberty Theatre, built in 1925, is a historic vaudeville theater and cinema with a classic marquee and ornate interior, hosting film screenings, live performances, and community events. Nearby, the Commodore Hotel is not only an ideal accommodation option but also offers a few dining spots worth discovering, including the brunch favorite Broder Strand and Stranded, a Scandinavian cocktail bar and eatery. For more to explore, head over to Duane Street to Fort George Brewery for a brewery tour while sampling some of the finest craft beers in the Pacific Northwest.
Discovering Oregon's Best Downtown Streets
Oregon has many smaller towns and cities, often surrounded by forests, mountains, rivers, and rolling valley vineyards, that are worth exploring on your next Pacific Northwest trip. From McMinnville’s wine country region and Ashland’s cultural streets to Pendleton’s Old West avenues, Sisters’ rustic Cascade charm, Forest Grove’s lively Pacific Avenue, and Astoria’s waterfront corridor, each destination offers a closer look at the state’s character. Their main streets, lined with shops, restaurants, galleries, and historic landmarks, provide experiences that highlight the diversity and everyday life found beyond Oregon’s larger communities.
