Discover the best things to do in Southern Oregon this September
Fall is one of the best times to experience everything Southern Oregon has to offer. From world-class theater and local festivals to food events, community celebrations, and outdoor adventures, the Rogue Valley comes alive with opportunities to connect, explore, and enjoy the season.
Whether you’re a longtime local or considering making Ashland, Medford, or the surrounding communities home, these September events are a great way to experience the culture and charm that make this region special.
🎭 A Midsummer Night’s Dream at Oregon Shakespeare Festival
Experience the magic of Shakespeare with A Midsummer Night’s Dream at the Oregon Shakespeare Festival in Ashland. Known for its incredible performances and vibrant arts scene, OSF has been a cornerstone of Ashland’s culture for decades.
This is the perfect fall date night, weekend activity, or opportunity to enjoy one of the region’s most beloved traditions.
🚗 Gathering at the Oaks Car Show 2026
Car enthusiasts won’t want to miss Gathering at the Oaks Car Show 2026, featuring classic vehicles, community connection, and a celebration of automotive history.
Events like this highlight the small-town charm and passionate communities that make Southern Oregon such a fun place to explore.
🎈 Moulin Ruch Festival of Flight & Jacksaphine Country Fair 2026
Bring the family and enjoy the Moulin Ruch Festival of Flight & Jacksaphine Country Fair 2026, a community event filled with creativity, entertainment, and local experiences.
It’s a great way to spend a fall day outdoors while supporting the people and organizations that make the Applegate Valley area unique.
🍷 Scottish Fish at Dos Mariposas Vineyards & Lavender
Enjoy a unique evening at Scottish Fish at Dos Mariposas Vineyards & Lavender.
With local wine country scenery, great food, and a beautiful vineyard setting, this event captures the relaxed lifestyle that makes the Rogue Valley such a special place for residents and visitors alike. The region is also known for its thriving wine culture, including the Rogue Valley AVA.
🧀 Rogue Valley Mac & Cheese Festival
Comfort food meets community at the Rogue Valley Mac & Cheese Festival.
Gather your friends and family for a fun-filled celebration featuring creative takes on a classic favorite. It’s the perfect fall event for food lovers looking to enjoy local flavors and a relaxed atmosphere.
⭐ Gala 2026: Britt Under the Stars
Celebrate the arts at Gala 2026: Britt Under the Stars.
The Britt Festival is one of Southern Oregon’s most iconic cultural experiences, bringing music, performances, and unforgettable evenings under the stars.
🚴 The Rogue Ride
Outdoor lovers can enjoy The Rogue Ride, a chance to experience the beauty of Southern Oregon while connecting with fellow cycling enthusiasts.
With scenic landscapes, charming communities, and year-round outdoor opportunities, it’s easy to see why so many people love exploring the Rogue Valley.
🍺 Oktoberfest at Mt. Ashland
Celebrate the season at Oktoberfest at Mt. Ashland.
Enjoy fall traditions, community gatherings, and mountain views while welcoming the arrival of autumn in true Southern Oregon style.
🌎 Greater Medford Multicultural Fair
Celebrate the diverse cultures and traditions that make the Rogue Valley community special at the Greater Medford Multicultural Fair.
This event is a wonderful opportunity to enjoy food, music, art, and experiences from cultures around the world.
🎌 Ani-Medford 2026
Anime fans can celebrate all things Japanese pop culture at Ani-Medford 2026.
From costumes and creativity to community connections, this event brings fans together for a fun and unique experience.
🚂 Medford Railroad Park Sunday Run Day
Families can enjoy a nostalgic day at Medford Railroad Park Sunday Run Day.
This local favorite is a great outing for kids and anyone who loves trains, history, and community events.
🎃 Scarecrow Harvest Festival at Hanley Farm
Welcome fall at the Scarecrow Harvest Festival at Hanley Farm.
Enjoy seasonal activities, farm traditions, and autumn fun in a beautiful historic setting. It’s the kind of community experience that makes Southern Oregon feel like home.
Why Southern Oregon is a Special Place to Call Home
From Ashland’s vibrant arts scene to Medford’s growing community and the natural beauty throughout the Rogue Valley, there is always something new to experience.
Local events like these are more than just weekend activities. They’re opportunities to meet neighbors, support small businesses, and discover the lifestyle that draws so many people to Southern Oregon.
If you’re thinking about making the Rogue Valley your home, exploring local events is one of the best ways to get to know the community.
Ready to discover what life in Southern Oregon could look like? Let’s explore what makes this area such a special place to live.
