The Best Things to Do in Southern Oregon This Memorial Day Weekend
Memorial Day weekend is one of the best times to get out and explore Southern Oregon. Whether you're looking for world-class theater in Ashland, family-friendly attractions in Medford, outdoor adventures, local wine experiences, or the excitement of the legendary Boatnik Festival in Grants Pass, there's no shortage of events happening across the Rogue Valley.
From jetboat races and live music to Shakespeare productions and community celebrations, here are twelve of the top events happening in Southern Oregon this weekend.
1. A Midsummer Night's Dream at the Oregon Shakespeare Festival
One of Shakespeare's most beloved comedies returns to Ashland with enchanting storytelling, memorable characters, and plenty of laughter. The production offers a perfect introduction to the Oregon Shakespeare Festival for first-time visitors while remaining a favorite among longtime theatergoers.
If you're planning a weekend in Ashland, this classic performance deserves a spot on your itinerary.
2. Boatnik Festival & Jetboat Races (Grants Pass)
Few Memorial Day traditions are as iconic in Southern Oregon as the Boatnik Festival in Grants Pass.
Each year, thousands gather along the Rogue River to watch high-speed jetboat races while enjoying a festive atmosphere filled with carnival rides, food vendors, live entertainment, family activities, and community celebrations.
Whether you're a lifelong local or visiting the region for the first time, Boatnik delivers an unforgettable Memorial Day weekend experience and remains one of Southern Oregon's signature annual events.
3. Come From Away at the Oregon Shakespeare Festival
This award-winning musical tells the remarkable true story of how a small Canadian town welcomed thousands of stranded airline passengers following the events of September 11.
Filled with humor, heart, and uplifting performances, Come From Away has become one of the most beloved productions in modern theater and continues to draw audiences from across the Pacific Northwest.
4. 360 ALLSTARS
Part urban circus, part extreme sports showcase, and part live concert, 360 ALLSTARS delivers nonstop energy and entertainment.
Featuring BMX riders, basketball performers, breakdancers, acrobats, and live musicians, this family-friendly event offers something for every age group and is one of the most unique performances happening this weekend.
5. A Raisin in the Sun at the Oregon Shakespeare Festival
This landmark American drama continues to resonate with audiences decades after its debut.
The powerful story explores family, ambition, and resilience while delivering unforgettable performances that make it one of the season's most talked-about productions.
6. Rogue Valley Symphony – Shining Star
Experience an evening of exceptional music with one of Southern Oregon's premier performing arts organizations.
The Rogue Valley Symphony's Shining Star concert showcases talented musicians and an engaging program that appeals to both longtime symphony fans and newcomers alike.
7. You Are Cordially Invited to the End of the World
One of the Oregon Shakespeare Festival's newest productions combines contemporary storytelling, humor, and thought-provoking themes into a unique theatrical experience.
For visitors seeking something beyond the classics, this production offers an exciting alternative.
8. Rolling Stones Mobile Skating Rink
Looking for family-friendly fun?
The Rolling Stones Mobile Skating Rink offers a nostalgic and entertaining experience perfect for kids, teens, and adults. Lace up your skates and enjoy a memorable holiday weekend activity with friends and family.
9. Rogue Memorial Challenge Soccer Tournament
Athletes and families from across the Pacific Northwest travel to Southern Oregon each year for the Rogue Memorial Challenge.
This popular youth soccer tournament brings exciting competition, community spirit, and plenty of action to local fields throughout the weekend.
10. Medford Railroad Park Sunday Run Day
One of Medford's most beloved attractions, Railroad Park offers miniature train rides, railroad exhibits, and hands-on fun for all ages.
It's a perfect outing for families looking to enjoy a relaxing afternoon together during the holiday weekend.
11. Memorial Day Weekend Live Music at Sams Creek Cellars
Spend the afternoon enjoying local wine, beautiful vineyard scenery, and live music at one of Southern Oregon's welcoming wineries.
Events like these showcase why the Rogue Valley wine scene continues to gain recognition throughout the Pacific Northwest.
12. Nick Garrett-Powell at RoxyAnn Winery
Live music and wine country are always a winning combination.
Enjoy an evening performance from local favorite Nick Garrett-Powell while taking in vineyard views and sampling wines from one of the Rogue Valley's most popular wineries.
Why Southern Oregon Is a Great Memorial Day Weekend Destination
Southern Oregon offers an incredible mix of experiences rarely found in one destination.
Visitors can spend the morning watching jetboat races in Grants Pass, enjoy an afternoon wine tasting in the Rogue Valley, and finish the evening with a world-class theater performance in Ashland.
The combination of outdoor recreation, cultural attractions, family-friendly events, wineries, and vibrant downtown districts makes Southern Oregon one of Oregon's most rewarding weekend getaways.
Planning a Move to Southern Oregon?
Many people first discover Southern Oregon while attending local events and quickly fall in love with the region's lifestyle, natural beauty, and strong sense of community.
Whether you're considering relocating to Medford, Ashland, Central Point, Jacksonville, Eagle Point, or Grants Pass, our team can help you explore neighborhoods, schools, market trends, and available homes throughout the Rogue Valley.
Thinking about making Southern Oregon home? Contact Rockwell Real Estate Group to learn more about buying or selling in the Rogue Valley.
Frequently Asked Questions
What are the best things to do in Southern Oregon this weekend?
Some of the most popular events include the Boatnik Festival in Grants Pass, Oregon Shakespeare Festival productions in Ashland, Rogue Valley Symphony performances, local winery events, and Medford Railroad Park Sunday Run Day.
What is the biggest Memorial Day weekend event in Southern Oregon?
The Boatnik Festival in Grants Pass is one of Southern Oregon's largest annual Memorial Day celebrations. The event features jetboat races, carnival rides, food vendors, family activities, and live entertainment.
Are there family-friendly events in Southern Oregon?
Yes. Boatnik Festival, Medford Railroad Park, the Rolling Stones Mobile Skating Rink, and the Rogue Memorial Challenge Soccer Tournament are excellent options for families.
What is happening in Ashland this weekend?
Ashland is hosting several Oregon Shakespeare Festival productions, including A Midsummer Night's Dream, Come From Away, A Raisin in the Sun, and You Are Cordially Invited to the End of the World.
Is Southern Oregon worth visiting during Memorial Day weekend?
Absolutely. Memorial Day weekend offers some of the region's biggest annual events, beautiful spring weather, winery experiences, outdoor recreation, and nationally recognized theater performances.
