9 Towns in Oregon With the Best Downtown Areas in 2024
As a traveler, there is nothing like learning more about a town by enjoying what its downtown offers. From its local shops and homegrown restaurants to vibrant activities that showcase its robust culture and heritage, a great downtown leaves a lasting impression and makes your trip memorable.
If you are traveling to the Pacific Northwest region, Oregon’s downtowns have all that in spades! With a mix of Native American culture, the great outdoors, farmer’s markets, music and wine, and European heritage, these towns in Oregon will make you sing Petula Clark’s classic Downtown song. As the song goes, “No finer place for sure—downtown. Everything’s waiting for you.” Well, let us not keep them waiting—here are 9 towns in Oregon with the best downtown areas in 2024!
Ashland
For a charming downtown experience, Ashland, Oregon, is a treasure trove waiting to be explored. Nestled in the foothills of the Siskiyou Mountains, Ashland is renowned for its Shakespearean charm and vibrant arts scene. A stroll through Lithia Park reveals a 93-acre oasis with serene duck ponds, vibrant flower gardens, and the soothing sounds of Ashland Creek. The Oregon Shakespeare Festival features world-class performances that grace the stages year-round.
Downtown Ashland is a haven for art lovers and food enthusiasts alike. Quaint streets are lined with eclectic shops, art galleries, and cozy cafes. Farm-to-table dining can be enjoyed at local favorites like Larks Home Kitchen Cuisine, or one might savor a leisurely coffee at Mix Bakeshop, known for its delightful pastries and scenic outdoor seating. The downtown offers a blend of historic architecture and modern boutiques, making Ashland a destination for those seeking culture, nature, and small-town charm.
West Linn
For history buffs, West Linn is one of the best downtowns in Oregon to visit due to its Historic Willamette Walking Tour, heritage trees, and meteorite display. The tour takes you through what once was a Native American trail, now lined with restored buildings and well-kept old trees acknowledged by the Arbor Day Foundation. Cap the tour off with a view of the largest meteorite in the US, the Willamette Meteorite, which the natives of the land discovered.
If you would rather sip and stroll, visit West Linn every fall for its Willamette Distillery/Spirit Stroll and Autumn Wine Walk. Want some vintage thingamajigs? Drop by the Vintage West Linn shop, an adorable bungalow-turned-store that sells vintage gifts and knick-knacks. The city also has a farmer’s market every summer, so you can grab a bite and unwind while viewing the great Willamette Falls.
Sisters
Named after the nearby volcanic mountains called Three Sisters, this town’s quaint Old West and mountain villa vibes are best experienced through its downtown live rodeos, three-day folk festivals, and Western-style inns. Sisters Rodeo is an annual summer event where pro rodeo athletes giddy it up for the crowd, while Big Ponderoo and Sisters Folk Fest celebrate the town’s love for Americana, bluegrass, and multi-genre music.
Visitors who are fond of arts and crafts might want to drop by around July for Sisters’ internationally recognized Outdoor Quilt Show, where master quilters from around the world display their stunning quilt designs. Before leaving, visit Raven Makes Gallery for contemporary Native American art or Canyon Creek Pottery for your very own Sisters-made pots and mugs.
Bend
A high-desert adventure with stunning mountain views and a vibrant craft beer scene awaits in Bend, Oregon. Sat along the Deschutes River, Bend is renowned for its outdoor recreational opportunities and bustling downtown area. Visitors often flock to Drake Park, a picturesque spot with lush green lawns, mirror-like ponds, and a riverfront walkway perfect for a leisurely stroll. For those seeking more excitement, the Old Mill District offers shopping, dining, and outdoor activities with the beautiful Cascade Mountains as a backdrop.
Bend's downtown is more than just an outdoor paradise. It boasts a year-round farmer's market, eclectic boutiques, and a thriving arts scene. Events like the Bend Summer Festival, Fall Festival, and WinterFest keep the town lively throughout the seasons. Local breweries, such as Deschutes Brewery and 10 Barrel Brewing, provide a taste of Bend's famous craft beer culture. With its mix of natural beauty, cultural events, and culinary delights, Bend is a must-visit destination for any traveler.
Silverton
For an absolutely picturesque downtown, Silverton is Oregon’s best-kept secret—a secret garden, if you may—since it is locally known for its botanical garden and idyllic downtown lined with trees and flower bushes. After stopping to smell the roses at the 80-acre Oregon Garden, head over to the Silverton Country Historical to know what life was like 150 years ago with the Silverton pioneers. You will probably see the town’s eye-catching murals along the way, which fit the vibe of the town’s weekend Crafter’s Market.
Almost everything in Silverton looks like art brought to life—from its vintage-gas-station-turned-coffee-shop at Silverton Coffee Station to The Noble Fox’s outdoor seating that overlooks Silver Creek River. If you are aiming for an Instagram-worthy place, Silverton should be one of your must-visit towns in Oregon with the best downtown areas in 2024!
Independence
Bringing in an exciting twist to the usual heritage walks, this Oregon town turns its historic walking tours into a “Ghost Walk” every October! Not only do you learn Independence’s history of being a port trading hub in the Willamette River and the “hop capital” of the area, but you will also get local lore and tales of the spectral nature of its historical downtown locations.
Not into the supernatural? The Independence Heritage Museum is always open, sans spooky, and the yearly Hop and Heritage Festival brings in hop-tastic fun through cornhole tournaments, craft beer, and live music. You can also enjoy the town’s flourishing business district that’s open year-round, like the sweet tooth paradise Melting Pot Candy, the cozy reading nook of Second Chance Books, and the enthralling artworks of River Gallery.
Brookings
A seaside escapade with magnificent views of the Oregon Coast and a charming azalea garden await you in the small Oregon town of Brookings. Being the only Oregon city worthy of the title “Azalea City of America”, visitors often take a weekend trip here to enjoy its Azalea Park, filled with ancient native azalea bushes lovingly cultivated by the locals. If you are up for a by-the-sea camping trip with birdwatching, Harris Beach State Park and its Bird Island are the go-to places. You can also go biking in Brookings’ bike-friendly streets and seaside parks.
As lovely as those are, Brookings has more to offer than flowers and sea breeze. Its farmer’s market is open the entire year, while its downtown is always busy year-round with events such as Brookings Downtown at Sundown summer concerts, Fall For Downtown during September, and Nature's Coastal Holiday for the winter holidays.
Lake Oswego
Lake Oswego downtown is a wonderful mix of scenic landscape, preserved history, and sophisticated shopping galleries. Spend the day at Oswego Lake and stroll through George Rogers Park to admire the town’s preserved furnace—a great reminder of what once was a booming iron industry in Oregon.
When here, do not miss the town’s upscale shopping complex, Lake View Village, to experience Lake Oswego’s fine dining options (Five Spice Restaurant, Lake View Taphouse) and gift shops (Glassybaby, Lucky Me Boutique). Finally, admire the trees and stars at Millennium Plaza Park to enjoy the heart of Lake Oswego’s downtown. Farmer’s Market, movies at the park, open-air concerts, and a fireplace you can hang out at are just some of the things you can do here.
Molalla
An adorable mini train park, farm stays, a toast or two at the town’s brewery, and a view of Molalla River are just some of the must-visit spots in Molalla, Oregon. Named after the river that was named after the natives of the area, Molalla offers visitors a laid-back way of life through its quaint downtown attractions and accommodations.
Learn more about its people and river namesake at the Dibble House Museum, then enjoy some drinks and some mini golf at Molalla River Brewing Company. If you are traveling with kids, they will get a kick out of the adorable Molalla Train Park and Molalla Buckeroo Rodeo! To fully experience the Molalla way of life, stay at one of its inns or farm stays, like Drizzlewood Farm or The Prairie House Inn, and visit during summer for the Celebrate Molalla festival.
Final Thoughts
While most Oregon towns are not as big, populated, and known as other cities in the United States, these charming towns are still rich in character and Oregon's uniqueness. It is still metropolitan without being too urban but with a sprinkle of “small town togetherness” and a good helping of scenic views from nature. From wine tasting and live rodeos to mini train rides and flower parks, consider visiting these towns in Oregon with the best downtown areas in 2024!
After all, a city’s downtown is often the heart and soul of a place. It can easily give you a glimpse of the area’s culture, history, and way of living. Instead of beelining to your next booked recreation, try to take some time to soak in the sights, culture, and vibe of your destination to make your trip truly memorable. “Stop and smell the roses,” as they say. You will not regret it!
