Wine is a big industry here in the Rogue Valley and we are fortunate to have so many beautiful wineries to enjoy! Our top recommendations near Ashland: Naumes Suncrest Winery, Irvine and Roberts and Paschal Winery and Vineyard. Some of our favorite wineries near Jacksonville are DANCIN Vineyards, Hummingbird Estate and Red Lily Vineyards. Red Lily is further out in the Applegate Valley, but we promise you it is worth the drive! There are multiple vineyards out that direction and wine tours are a common way to explore this special area! Here is a link to some local wine tours if you're interested: https://travelashland.com/wine-tours/
The Rogue River is one of our favorite parts of living in the Rogue Valley. Whether you want to float a mellow section or spice it up and enjoy a jet boat ride or embark on a guided rafting trip, the Rogue River has something to offer for everyone! You can also do a half day or a full day adventure if you are staying longer and making a trip of the weekend! Here is a link with more local resources: https://www.travelmedford.org/rivers
Whether you want to mountain bike, trail run or hike- the Rogue Valley has so much to offer! Our top recommendations would be a mountain bike shuttle with Ashland Mountain Adventures. Bike rentals available! There are also countless mountain biking trails above Lithia park. Here is a link for more information: https://ashmtnadv.com/?page_id=21
Both Ashland and Jacksonville have lovely hiking trails. Some of our favorites in Ashland include the Lithia Park trails and Grizzly Peak Trail. Our favorites near Jacksonville include The East Applegate Ridge Trail and the Britt Trails.
The Shakespeare Festival is a big deal in Ashland and will have shows in June. If you have time, experience the outdoor theater! Here is a link to the shows:
There is also the Oregon Cabaret Theater in Ashland and the Britt Musical Festival in Jacksonville that brings in some great shows! Check it out if you are trying to make a longer weekend trip! Here is a link to the Britt Music Festival: https://www.brittfest.org/