It might be the perfect season to explore this 1850s gold-rush boomtown, when tree-lined streets erupt into rich shades of ambers and reds, matching the town’s historic brick boutiques and one-of-a-kind vintage shops. 

The autumn harvest brings incredible culinary and tasting experiences. In the heart of Southern Oregon wine country, recently named the #2 wine region in the U.S.—Jacksonville offers easy access to dozens of nearby vineyards and tasting rooms. Riding the Wine Trolley from the center of town through the rolling vineyards makes for an unforgettable afternoon of wine tasting, while the town’s History Trolley is fun for families of all ages. 

Surrounding Jacksonville’s main historic street, nature and beauty intertwine through the shaded trails of the Britt Gardens. Spend the morning on a wandering hike, then catch one of the nightly live music concerts by local artists.

 Enjoy the sunset from the veranda of your historic hotel while sipping a regional vintage, or walk to town for a late-night dessert with friends. Wood-fired pizzas are a local favorite. 

Just four hours from Portland and minutes to the Medford International Airport, Jacksonville fall offers the most magical weekend getaway you can find in the Pacific Northwest. 

Book by Oct. 1 at any Jacksonville lodging with code TROLLEY26 and get two complimentary History Trolley Tickets. 

jacksonvilleoregon.org