From the towering peaks of Mount Hood to the beautiful rocky Pacific Coast, Oregon is a breathtaking destination. Whether you’re looking for a Memorial Day celebration in Portland or seeking out a patriotic event near Grants Pass to honor the military, there are plenty of activities and attractions to fill up your extended weekend. Start your search for Oregon vacation rentals, and consider these top nine cities and towns for your itinerary.
1. Willamette Valley
Memorial Day weekend kicks off the summer-long wine tasting season in the Willamette Valley. More than 150 wineries open their tasting rooms to celebrate Oregon’s wine month. Even some of the smallest vineyards that normally close their doors to the public are available for a look. The Valley is a 150-mile-long valley located in the Pacific Northwest and travels through the Cascades and Calapooya Mountains and along the Oregon Coast. Stop by the Blooming Hill Vineyard in Cornelius, which offers a long-distance wine club. Sign up to get a flavor of the month and discover something new. The Anderson Family Vineyard in Newberg provides private tours of their vineyards, and the Bravura Cellars has a wine club just for individuals who love bold red wines. Stay in a central vacation rental in the region, and enjoy a selection of excellent foods and good music.
Find vacation rentals in the Willamette Valley
Opening for the season on Memorial Day weekend, the Mt. Hood Skibowl Adventure Park has the only half-mile dual Alpine slide in the Pacific Northwest. There’s also a zipline for the adventurer, mini golf for younger children, disc golf, and batting cages for those who want to get in some ball practice while on vacation. If you love horseback riding, the park offers trail rides, and there are also mountain bike trails if you want to bring along your bike. On Memorial Day weekend, all active and inactive military personnel get in free. On Monday, be sure to attend South Portland’s Memorial Day Parade, which runs from the Southern Maine Community College to the Service Monument in Millcreek Park.
Find vacation rentals in Portland
SMaSH Fest is a large music festival held during the Central Oregon Beer Week every Memorial Day. The event takes place in Bend, where an array of musicians gathers to give a weekend-long concert. Other activities include a guided Bend Ale Trail hike, movies under the stars, tasting rooms, and dancing, and there is plenty of food to sample and enjoy. While in Bend, be sure to tour the High Desert Museum, which has a variety of exhibits and artifacts from the region, or go swimming at Tumalo State Park.
Find the perfect Oregon vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!
4. Junction City
If you’re into sailing, you know that Memorial Day also kicks off the sailing season. Fans of the event can sign up to take part in the annual Memorial Day regatta that attracts sailors from all across the northwest. The event takes place at the Fern Ridge Reservoir and Wildlife Area in Junction City, and sign-ups take place online at the Regatta Network. After the race, head to the Pfeiffer Winery for live music and food, including grilled-cooked burgers and barbecue. There is also a beautiful water garden to explore and take pictures.
Find vacation rentals near Junction City
5. Klamath Falls
Attend a day-long list of events in Klamath Falls on Memorial Day. Start with a free breakfast at the American Legion, which features pancakes and ham, then attend the Memorial Day Parade that starts at the Klamath County Museum and ends at the Veterans Memorial Park. Veterans tend to throw candy to onlookers, so be sure to bring a bag. For early risers, the Veterans of Foreign Wars hosts a sunrise service at the Klamath Memorial Park, where officers make speeches and place flowers around the memorial. The ceremony ends with the playing of “Taps” and a salute. Klamath Falls is also home to the Klamath County Museum, where you can learn about the history of the region. You can also escape your vacation rental and have a Memorial Day picnic at Moore Park, which has a playground and bike trails.
Find vacation rentals in Klamath Falls
6. Grants Pass
Grants Pass is a beautiful place to spend Memorial Day weekend if you are looking for a service to attend. The Marine Corps League holds an annual Memorial Day Observance Ceremony at the Hillcrest Memorial Park. The hour-long event includes a posting of colors, a gun salute, and speeches from various retired military members. More than 1,000 flags dot the landscape in the park to honor those who served. Afterwards, stroll along the historic district where you can take a self-guided tour through buildings built in the 1800s. There are several art galleries to explore and coffee shops in which to sample pastries, including the Grants Pass Museum of Art and Rogue Roasters.
Find vacation rentals in Grants Pass
Part of the Memorial Day weekend celebration, the Azalea Festival in Brookings offers a host of activities for families and individuals looking for a getaway. Kick off the weekend at the carnival in downtown, where you can ride the Ferris wheel and sample the cotton candy. Get up early Saturday for the Azalea Street Fair, which includes a parade through downtown. There’s live music, food, and plenty of arts and crafts booths. On Sunday, the festival hosts the shrimp feed, where you can enjoy a variety of shrimp dishes with the family. The Oregon Air National Guard takes to the sky on Monday in honor of Memorial Day, where you can watch as an F-15 fighter jet from the 173rd Fighter Wing flies overhead at the Brookings Airport.
Find vacation rentals in Brookings
Attend the annual Memorial Day weekend events in Eugene. Take a guided tour of the Eugene Masonic Cemetery, and listen and pay respects as “Taps” is played at noon each day. You can also enjoy hot dogs, chili, cookies, and bottled water. A parade travels through downtown, and afterward, you can stroll through the stalls at the Saturday Market on Oak Street. Here, you can listen to live music, sample international cuisine, and find over 200 artists that sell crafts.
Find vacation rentals in Eugene
Held on Memorial Day, the annual car show in Wasco is free for anyone who wants to display a treasured antique automobile. The event starts with the Memorial Day Parade through downtown. Participants can show off their vehicles in the lineup. There are also trophies for favorites, and you can enjoy food and music. Learn more about the region at the Wasco Historical Society and Museum, then take the kids to Westside Park for a picnic. Annin Park is an excellent place to go for hiking, or you can head to White River Falls State Park to enjoy the 90-foot falls.
Find vacation rentals in Wasco
Ready to go? Check out these amazing Oregon vacation rentals on Tripping.com.