Chamber Chat – May 2026
JACKSONVILLE IS CELEBRATING May with a lineup of activities highlighting its charm, culture, and natural beauty. The month features events for Mother’s Day, local music & arts, romantic getaways, Oregon Wine Month, and expanded Wine Trolley and Historic Tours.
Jacksonville’s historic district comes alive with floral displays, outdoor dining, and family-friendly experiences. Highlights include complimentary Wine Trolley rides for Mothers, special brunch menus at local cafés and inns, and a garden and heritage walk through the National Historic Landmark District. Visitors can also enjoy spring shopping specials at artisan boutiques and galleries.
May in Jacksonville blends live music, wine country ambiance, and outdoor dining into a month-long celebration of spring. Whether you are sipping wine at a local lounge, enjoying a patio dinner under warm evening light, or catching a weekend performance at a local restaurant, the town offers a relaxed, festive rhythm all month long.
Jacksonville’s boutique inns, historic bed-and-breakfasts, and guest cottages offer a perfect setting for romantic getaways. Couples can enjoy fireplace suites, garden courtyards, and vintage architecture. Romantic packages include wine, dining, and spa experiences, while twilight strolls through preserved 19th-century streets and woodland trails add to the charm.
Oregon Wine Month coincides perfectly with the kickoff of our Wine Trolley season. This is our third year of a successful partnership between the Chamber of Commerce and the Jacksonville Wine District. The Wine Trolley Shuttle provides hop-on/hop-off access to local wineries, downtown shops, and tasting rooms. Ticket options include a one-day pass, three-day weekend pass, and a happy hour pass, each ticket including one free tasting at each participating winery.
Complimentary trolley rides are available for mothers on Mother’s Day weekend, fathers on Father’s Day weekend, and recent graduates during the first week of June. Narrated Historic Tours explore Jacksonville’s Gold Rush history, Victorian architecture, and cultural landmarks, providing storytelling and photo opportunities. Jacksonville also serves as a gateway to the Applegate Valley Wine Trail, making it an ideal hub for wine enthusiasts.
For more information, visit www.Jacksonvilleoregon.org or contact the Jacksonville Chamber of Commerce at 541-702-7060. Our summer Visitor Center hours are Tuesday through Sunday, 10am-3pm.
Featured image: Belles & Beaus of Jacksonville l-r Michael Klosterman, Theresa Schumacher, Michael Body