The Best Small Town In Oregon For A 3-Day Weekend
A perfect weekend getaway needs three things: a great place to stay, a welcoming community with plenty to see and do, and some natural wonders to take in. With Oregon’s varied landscapes and climates, it is rich with options, but a clear choice for a town that has everything is Hood River. Nestled in the Columbia Plateau, the town of Hood River is where the Columbia River and the Hood River meet. A town of 8,313, with a port on the Columbia, Hood River’s economy was founded on lumber, with tourism, and high-tech industries, particularly aerospace engineering, becoming increasingly important. As the lumber industry declined, the agricultural focus shifted to fruit orchards and winemaking.
A walkable town beneath the backdrop of Mount Hood, Hood River provides amenities and activities ideal for the weekend getaway. Its proximity to Portland, as well as Vancouver, Washington, makes Hood River a convenient place to escape the city. With its focus on fruit agriculture, wineries, and breweries, Hood River is renowned for its annual festivals, including the Hard-Pressed Cider Fest in April, as well as the Hood River Hops Fest and the Hood River Valley Harvest Fest, both held in the fall.
Downtown Historic District

With a clear view of the Columbia River, Hood River’s downtown Historic District offers a diverse range of shopping experiences. With so much natural beauty around it, it is no surprise that Hood River has stores dedicated to outdoor adventures and gear outfitters. There are plenty of shops to cater to any need, including boutiques and designer shops, wonderful antique shops, galleries, and many cafes, pubs, and restaurants. The historic buildings that line the district are very much part of the appeal of this area.

G. Willikers Toy Shoppe has been a fixture on Oak Street for over twenty years. With a range of toys for kids of any age, this family-owned business is the go-to spot for both classic and contemporary toys. The wonderful thing about G. Willikers Toy Shoppe is that it focuses on the kinds of play that big stores tend to ignore, from a wide range of board games, books, art and craft supplies, science and engineering-based toys, and outdoor activities. For antiques on Oak Street, Cajun & Clover offers vintage goods from the 1800s all the way through Art Deco, mid-century modern, and the wild colors of the late 1960s and 1970s. Located on the waterfront and featuring great views and atmosphere, Stoked Roasters + Coffeehouse is a great find for coffee roasted on-site. They have a tasting room with pastries available, and they are family-owned, so the atmosphere is focused on the customer’s experience.
Places to Stay

There are numerous accommodation options available in Hood River. With its rich history and stunning natural beauty, Hood River has been welcoming tourists for generations. Whether you’re looking for a high-end luxury experience, a funky boutique place to crash, or you are looking for something more earthy and rustic, Hood River has you covered. For a grand hotel experience, Columbia Gorge Hotel & Spa is set against the beautiful waterfalls of the Columbia Gorge. They offer everything you expect from a luxury hotel, with rooms facing either the Columbia River or the beautiful hotel gardens. There is a full-service spa, and an exceptional restaurant featuring European and local cuisines and emphasising locally-sourced ingredients.

Right in the downtown Historic District is Thistledown on Oak, a boutique hotel. Set in the top floors of the historic First National Bank Building, Thistledown on Oak is a 19th-century themed hotel, set right in the heart of Hood River’s commercial center. This is a great choice for those looking to explore the town, but it also functions well as a base for exploring further into the surrounding countryside. For a more rustic experience, Backwoods Cabins are private cabins located right in the Columbia Gorge. These craftsman-style cabins are surrounded by a pine forest, and while there is definitely a back-to-nature atmosphere at Backwoods Cabins, they nevertheless feature all the modern amenities you expect. They also offer drinks and food at their Backwoods Pub.
Historic Hood River

Hood River’s history is an important draw for travelers, with many buildings dating from the late 19th century and early 20th century. The Historic District itself is lined with preserved buildings from the 1800s to the 1930s, many now housing shops, places to eat, wineries, and breweries. Located at 10th and Montello, a short walk from Oak Street in the Historic District, the Simpson Copple House is a late vernacular, or folk style, Queen Anne house built in 1906. Noted for the fine detailed work on its gables, making it a unique example of that period and style of architecture. The building is open to the public as it now houses an agricultural tourism organization that focuses on local foods, wine, and cider.

Also built in 1906, the I.O.O.F./Paris Fair Building is a former department store that also housed an International Order of Odd Fellows meeting hall. A great example of American Commercial architecture, it is located on Oak Street. It currently houses private businesses and is accessible during opening hours. An Egyptian Revival building designed by AE Doyle, the Butler Bank building was built in 1924 on Oak Street and 3rd. The building now houses the 301 Art Gallery, and there is also an apartment on the top floor available as a guest house.
Natural Wonders

The Columbia River Gorge runs through two states and 13 urban areas, with the Columbia River at its center. Part of the Cascade Mountain Range, the local geology creates what is known as the rainbow shadow effect, where the West end of the Gorge consists of lush conifer forests, while the East end is grasslands, all due to the differences in precipitation. The Columbia River Gorge National Scenic Area is part of the Forest Service of the United States Department of Agriculture. The Gorge is a river canyon up to 4,000 feet deep, with varied landscapes of cliffs, ridges, and over 90 waterfalls. To visit, there are day passes, longer-term passes, and annual passes.

For scenic drives, the Hood River Fruit Loop is a 35-mile loop through 14,500 acres of the Hood River Valley with over 30 fruit farms, wineries, breweries, and cideries. When in season, you will find plenty of fruit stands set up by local farmers along the route. The views of the Gorge, Mount Hood, and the rolling hills of the valley countryside are spectacular. From Hood River, you take Highway 35 and loop around to Highway 281 and back towards Hood River. The full loop takes about a day, but you can customize your trip by visiting a few stops before heading back. You can also wander off the route into the smaller country roads if you're feeling adventurous.
Three Great Days in Hood River
Whether you want a 3-day weekend filled with activities and adventures, or you want some time to do absolutely nothing, Hood River, Oregon, is the perfect choice. Deep with history, culture, and natural wonders, you can find plenty to do, from wine tours, kayaking on the Hood River, hiking through the endless trails of the Columbia River Gorge, to relaxing in your luxury accommodations, with a panoramic view of the Columbia River. Hood River is a great escape, close to major urban centers, but far enough away to get that small-town ambience.