The Best Small Towns Near Portland for a Weekend Getaway

st helens

Even with its small-town feel, Portland can feel a bit tiresome at times. Though living in the biggest city in Oregon has its perks, sometimes you just need to get away. Luckily, there’s no shortage of escape routes in the PNW. Sure, you know where to hike, kayak, and scale a mountain, but what about finding some r&r in a small, rural town? Local wineries, quaint bed and breakfasts, and stunning views await you, sometimes within 30 minutes of PDX. Check out some of the best small towns near Portland for when you just have to get away.

Best Small Towns Near Portland

Yamhill

small towns near Portland - saffron fields vineyard in Yamhill
Saffron Fields Vineyard’s Japanese Garden. Photo via Saffron Fields Vineyard.

Located in the heart of the Willamette Valley, Yamhill is surrounded by vineyards growing Oregon’s famous pinot noir grapes. Learn about the valley’s rich farmland with wine and culinary tours, or post up by the onsite koi ponds and Japanese garden at Saffron Fields Vineyards and simply enjoy the fruits of someone else’s labor. Take a stroll downtown before stopping at The Farm Store at Kookoolam Farms for hyper-local foods and a taste of cold-pressed honey wine. Afterward, snag a bottle to bring home to your cozy digs at the Yamhill Vineyards B&B.

Silverton

oregon garden - small towns near portland
The Oregon Garden in Silverton. Photo via The Oregon Garden.

Silverton is a great destination for those looking to get out of the city and channel small-town energy. With the Cascade Mountains looming in the background, historic covered bridges and local wineries seem even more quaint. The biggest boast in this town is its 80-acre botanical garden named simply, The Oregon Garden. Swing by the Silverton Coffee Station first for a bit of java, then peruse the 20+ gardens with the leisure of someone who doesn’t live in a big city. If you’re in more of a hiking mood, check out the beautiful Silver Falls State Park near the city. Polish off the day with a pint at Mac’s Place, and stay for the live music.

Boring

Clackamas River - small towns near Portland
Floating on the Clackamas River. Photo via TravelOregon.

Don’t let the name fool you, Boring can be a town of mild excitement. It is, after all, built over a lava field. Located along OR Route 212, Boring is an unincorporated community in Clackamas county. With dramatic views of Mt. Hood nearby, you can take an adventurous float down the Clackamas River, or hike the Cazadero Trail and do some berry picking. Made the quick skip down Highway 26 to visit Boring Brewery for quality brews in unassuming digs, and be sure to visit the North American Bigfoot Center on your way out.

St. Helens

st helens
St. Helens riverfront. Photo via TravelPortland.

Nestled along the Columbia River and Scappoose Bay, St. Helens was a historic stop on the Lewis and Clark Expedition in 1805. Pop culture fans may recognize the landscape, as it was used in several movies, including the PNW-based Twilight series. Enjoy one of the several parks and walking trails along the riverfront, or relax among the charming shops, restaurants, and breweries of the Olde Towne district. Sip an old fashion and enjoy local Chinook salmon at The Klondike Tavern, housed within the possibly haunted St. Helens Hotel.

Troutdale

troutdale - small towns near portland
Downtown Troutdale. Photo via OregonLive.

In 1872, sea captain John Harlow bought a pocket of land at the confluence of the Sandy and Columbia rivers. There he built an expansive estate filled with trout ponds that he came to call Troutdale. Nowadays, Troutdale is known as the gateway to the Columbia River Gorge. On the way in, be sure to drive past the now Insta-famous Multnomah Falls and snap a pic if you like. You can then take to the Glenn Otto Community Park for swimming and fishing, or peruse the shops along the Columbia River Highway. Enjoy the upscale opulence at Riverview Restaurant, or tuck into the rustic vibes of Ye Olde Pub.

About Author

Editor In Chief of Renegade PNW. Music lover & witchy woman.