7 of the Most Walkable Towns in Oregon (2024)

Oregon is best known for its rich contrast in the landscape. From the majestic Cascade Mountains to the dramatic river canyons along the Columbia River, the Beaver State is absolutely stunning. It's home to Crater Lake, the deepest lake in the country, and Mount Hood, the highest peak in the state. The natural wonders here attract millions of visitors from afar, bringing in $14 billion annually in tourism dollars. Given the state's popularity, the picturesque towns of Oregon prioritize making it easy for visitors to get around. A vital aspect of that is a town's walkability.

Portland is the fifth most walkable city in the country, while the quaint little towns of Ashland and Milwaukee received high pedestrian-friendly scores, too. The communities designed their infrastructure with foot traffic in mind by incorporating connecting sidewalks and directional signage. Traffic calming measures are implemented for safety, and there's easy access to trollies and buses to transport visitors to places not within walking distance. From towns in the high desert region to communities along the dramatic coastline, discover the most walkable towns in Oregon for your next memorable trip to the Pacific Northwest!

Ashland

Nestled in the Rogue Valley and surrounded by the Cascade and Siskiyou Mountains, one will find the laid-back community of Ashland. The progressive town is known for its vibrant art scene and is home to Southern Oregon University. The community is environmentally conscious and advocates for bicycling and walking. With that said, there are connecting sidewalks to navigate visitors from the lively downtown area to the Historic Railroad District.

The Historic Railroad District has a fantastic culinary scene, unique local shops, and quite a bit of history. Visitors can stop at the Ashland Depot Hotel to learn about the beginnings of the Southern Pacific Railroad, a fundamental part of the town’s development. In the early days, the railroad boosted the success of the milling, manufacturing, and livestock industries and brought settlers in during the gold rush. From there, visitors can take a stroll on sidewalk paths that lead to the Oregon Cabaret Theatre to watch a musical or comedy. Ashland is known for theatre and attracts thousands of visitors to events like the Oregon Shakespeare Festival each year.

About a 7-minute walk from the theatre is the historic John McCall House, which has been transformed into a boutique hotel. The home was built in the late 18th century for the founder of Ashland Woolen Mill and Ashland Library. It’s a great example of Italianate residential architecture. The rooms are stunning and elegant, and a delicious breakfast menu is offered in the morning.

Bandon

Located on Oregon's coast on the south side of the mouth of the Coquille River, one will find Bandon. The old town has darling Victorian-style storefronts with colorful awnings and a thriving art scene. To keep the ambiance calm and relaxing, the town has made it easy for visitors to get around without a car. Travelers can visit the Bandon Historical Society Museum, which highlights the area's early days with Native American artifacts, logging, fishing, cranberry farming, and the disastrous fire in the late 1930s. Historic markers around town educate people about the significance of the fire and how 450 buildings burned to the ground. From there, Bandon's beaches are a brisk walk away. In the summer, unique environmental art events take place, such as Circle of the Sand, where artists create meditative labyrinths in the sand.

An iconic place to eat right downtown is Tony's Crab Shack. It has been around forever and has old photographs on the walls of people who have come to enjoy the seafood. After a delicious dinner, a nice place to stay close by is the Bandon Inn. It sits on a bluff overlooking downtown, the marina, and the Pacific Ocean.

Sisters

Located on the east side of the Cascade Mountains in central Oregon in the Bend area, one will find the rustic town of Sisters. There's much Old West history here, evident while strolling downtown. There's a mixture of boutiques, antique shops, and art galleries you can walk to, as well as historic sites that have been converted into hotels and restaurants. One example is the Sisters Saloon and Ranch Grill in the historic Hotel Sisters. The renovations reflect the craftsmanship of when it was built in 1912. Visitors who are curious to learn more about the region's history can head to the Three Sisters Historical Society Museum. The space tells the story of how Sisters was established at the intersection of two cross-Cascade wagon roads and was primarily known as a lumber-producing town.

Sisters is also an outdoor lover's paradise. During the summertime, mountain biking is very popular. There are mountain bike rental shops downtown that are easy for pedestrians to find. Bicyclists can ride from downtown rental shops to popular trails. The Peterson Ridge Trail is located on the south end of town.

Sisters Bunkhouse is a unique place to stay in the heart of downtown. Large groups can rent the entire bunkhouse. Several hiking trails are within walking distance from the bunkhouse for easy access to outdoor adventure.

Cannon Beach

Cannon Beach is a charming seaside village with a beach vibe setting and stunning Pacific Ocean views. The downtown, oceanfront lodging, and popular sights are all within walking distance. Connecting pathways lead visitors to souvenir shops, outdoor restaurants, and gorgeous public beaches. The downtown area is clearly marked with signage to help direct visitors. There's a vibrant art and culinary scene and a fascinating historical past. At the Cannon Beach Museum, visitors can learn how Cannon Beach received its name. Cannons washed ashore following a shipwreck when a boat tried to cross the Columbia Bar. Visitors can also tour historic sites on foot on the Cannon Beach Historic Walk.

The downtown area is within walking distance of Cannon Beach. Tourists can marvel at the iconic Haystack Rock, which the area is known for. In the off-season, there's a good chance visitors will see gray whales migrating, which peaks in March to April. In the spring, thousands of whales go to the summer feeding ground in the Arctic.

The Hallmark Resort and Spa is the closest resort to Haystack Rock. The rooms have ocean views, and the hotel is within walking distance of downtown. There's a spa on the property, and visitors can rent bicycles to cruise around town.

Jacksonville

Jacksonville is an example of a western gold boom town. It's one of Oregon's oldest communities, and the entire town is considered a National Historic Landmark. The historic downtown is preserved 18th-century architecture, and all shops, restaurants, and businesses are independently owned. Jacksonville is a popular tourist spot for wine tasting, live music, tasty food, and outdoor recreation. Most of the sites are within a pleasant walk from Main Street. If visitors want to explore southern Oregon's wine country, it's easy to find the wine trolley that departs from downtown. There are four tasting rooms downtown and seven wineries outside of Jacksonville.

As far as history goes, an interesting way to learn about the town's past is to visit the historic Jacksonville Cemetery. It has been around since the mid-18th century. Visitors can hear tales about the town's founding families and their personal histories during walking tours.

The Mcculley House Inn is an idyllic place to stay in the heart of downtown. It has a gorgeous garden area outside, and the rooms have a historic feel and are decorated with elegant furniture. It's the oldest house in the state operating as an Inn.

Astoria

Surrounded by rivers and lush forests, Astoria is located in the northwestern corner of Oregon, where the Columbia River flows into the Pacific Ocean. It’s considered the oldest town in the state and has close historical ties to the Lewis and Clark Trail. The community has a walkable downtown and a revitalized waterfront, which makes it easy for visitors to explore. The Sixth Street Viewing Dock provides impressive views of the Astoria-Megler Bridge, which stretches four miles across the mouth of the Columbia River from Oregon to Washington. Another point of interest is the towering Astoria Column atop Coxcomb Hill, a tribute to the pioneers who built the West.

Astoria Riverwalk Inn is Astoria’s first waterfront hotel located near the riverwalk. Some of the rooms have balconies with magnificent views of the harbor. The inn lists every historic building and landmark in Astoria, making it easy to plan a self-guided walking tour around town.

Milwaukie

One will find the former mill town of Milwaukie about 6 miles outside Portland, on the east side of the Willamette River. It's known for its walkable downtown, full of shopping, wine bars, and taprooms. There are still several historic storefronts you can learn about, such as William Schindler Building, the oldest commercial building still standing. The downtown area comes to life on the weekends and holds a farmer's market every Sunday. For history buffs, the Milwaukie Museum is located in the historic Wise House and highlights how the land is home to the Clackamas Indians. When settlers arrived, shipbuilding, timber, and milling industries fueled development. Many of Milwaukie's shops, sites, and attractions are centrally located downtown, making the town perfect for a getaway on foot.

While visiting this sweet town, staying somewhere close to the Willamette River is ideal. The sound of the river flowing and the gorgeous natural setting are perfect for a weekend away. There are plenty of houses and condos to stay at that are listed on short-term rental sites like Airbnb.

From Sisters to Jacksonville, it's quite easy to tie up your shoelaces and walk to unique attractions and historic sites in the Beaver State. Paths will guide you to Oregon's treasures, such as the Oregon Trail. You can also walk to one of the 7,000 gorgeous bridges in the region in places such as Astoria. The downtown spaces prioritize foot traffic and have everything one needs. Visitors can shop at the eclectic shops in Cannon Beach or indulge in culinary excellence in Ashland. Travelers will benefit from ending their day by walking to their hotel. Oregon is a beautiful state that varies significantly from the high desert to the moist and rainy coast. After a long commute driving here, it's nice to know one can keep their vehicles parked and enjoy what the small towns offer.

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