7 Prettiest Downtown Strips In Oregon
Planning a trip to the Beaver State? Oregon is no lightweight when it comes to breathtaking destinations, and its downtowns alone are worth the trip. Most visitors like to visit Crater Lake National Park, explore the Oregon Coast, or hike in the Columbia River Gorge, but the small towns here are the real prize, offering some of the friendliest faces and prettiest places. At least 15,000 years ago, this area was a hospitable land during the time of the Paleo-Indians, and it has remained so ever since. The wet oceanic climate means you can enjoy rainy winters and dry, pleasant summers, making any time of year a good time to experience Oregon’s splendor.
Ashland
Things are quite green in Ashland, known for the Oregon Shakespeare Festival. Plays run from late February through October each year at the Oregon Shakespeare Festival east of town. East Main Street becomes quite an exciting place at that time, but even in the off-season, the area is still quite pretty. Colorful Edwardian-era buildings are sure to steal your gaze, and the Butler-Perozzi Fountain adds a touch of beauty to complement its history.
On that note, the Japanese Garden just south of that is one spot you do not want to miss. The Downtown Plaza, with its mix of modern architecture and open-air cafes, creates the perfect contrast—always full of energy, yet just steps away from the beauty of the garden for a stroll!
Jacksonville
This small community in Jackson County, Oregon, enjoys a lot of activity on its East California Street. The downtown area in Jacksonville is a historic district, with the Historic Jackson County Courthouse serving as the centerpiece of the rich history, especially noticeable with the surrounding Victorian houses.
The architecture in this district is quite beautiful, and the Beekman House—the local museum—is known to make visitors feel as if a time portal has opened. This attraction is especially popular during Christmas celebrations, showcasing how Victorians once celebrated the holidays—if you are prepared for a long walk.
McMinnville
If you are a fan of wine, then McMinnville is sure to bring you cheers! 3rd Street is lined with beautiful greenery, as well as a variety of wine tasting venues and wine bars. Whether you head on over to Pinot Vista Tasting Lounge or the nearby Troon Vineyard, a few hours is not nearly enough to enjoy all this small wine-loving community has to offer. On the same street, there is also a charming spot where you can rest and take pictures near a statue of a former U.S. president: the “Ben Franklin on a Bench” around the corner. This attraction is exactly what it sounds like, and the bronze figure has attracted many tourists eager to take photos.
Hood River
By the Columbia River sits this small town with a windsurfing culture. The small town of Hood River, a superb go-to, enjoys a waterfront downtown with a love of art. The Columbia Center for the Arts stands just north of the Laurel Gallery and adds a significant touch of beauty and culture to the heart of downtown.
Aside from the incredible scenic areas around the river, you can also visit the History Museum of Hood River County near the marina, where you can learn all about the region's rich heritage! The nearby Port Marina Park is also a perfect, relaxing waterfront area great for unwinding at the end of the day.
Joseph
Originally named Silver Lake and later Lake City, the small town of Joseph celebrates the region’s Native American and frontier history. A stroll downtown can lead you to the Wallowa County Museum, where you can check out some of the most interesting antiques and artifacts for which the town is known.
What gives this town its beauty is places like the Valley Bronze Gallery. This spot is a must-visit while exploring the bustling downtown area, with its gorgeous art pieces and masterfully crafted bronzework that really bring out the spirit of this small community. You can find similar treasures at the Phinney Gallery of Fine Art across the street.
Sisters
If you are looking for beautiful trees and flower-filled sidewalks, this small town in Deschutes County is the perfect place to explore and unwind. In the heart of town, Fir Street Park is a great first stop for a picnic—unless you are just coming back from the historic Sisters Saloon & Ranch Grill. There are plenty of great eateries downtown, but nobody captures the Old West charm quite like this local favorite.
For local history, the Sisters Museum is within walking distance. This recently restored 1930s home may be small in size, but it more than makes up for it with its storytelling of European and American settlers.
Astoria
When it comes to scenic riverwalks, Astoria stands out as the champion, offering a unique blend of historic Victorian homes and unmissable maritime murals. The Astoria Column is the first thing you will notice when you enter this incredible place; it is a 126-foot column depicting Oregon’s history, all viewable from an observation deck.
The busiest streets, however, are by the Columbia River. In addition to the river’s beauty, you will also find adventure, like the Astoria Underground Tours, and history in places such as the Columbia River Maritime Museum. The downtown area is kept especially lively by incredible sights near the Pacific Ocean, with the Astoria Riverwalk Viewpoint serving as the crown jewel—a must-see.
Final Thoughts
Oregon is home to some of the friendliest townsfolk and most attractive downtowns, often found in its smaller communities. While grand monuments and bustling cities can be worth visiting, even the smallest downtown strip may hide some of the state's best-kept secrets. Whether you are strolling through a farmers market or sipping coffee at a local café, every step along these streets feels like a journey through the heart of the Beaver State!
