Chamber Chat – June 2026

JACKSONVILLE IS stepping into June with the full charm, color, and character that only a true three-trolley town can offer. Our trolleys have become more than transportation—they are part of the Jacksonville experience, weaving together our history, our wine country, and our year round celebrations in a way that feels uniquely ours.

This season, all three trolleys are rolling: the beloved Narrated History Trolley, the ever popular Wine Trolley Shuttle, and our festive Holiday & Special Event Trolley, starting in late-June. They support everything you can imagine from parking shuttle services, weddings, private rentals, and community fundraisers. Each trolley brings their own personality, but together they tell the story of a town that values connection, heritage, and hospitality.

Our History Trolley continues to be a favorite for visitors and locals alike. With knowledgeable drivers and docents, the tour winds through Jacksonville’s Gold Rush past, Victorian architecture, and preserved landmarks. It is a reminder of how much of our story still stands proudly today—and how much we enjoy sharing it.

The Wine Trolley is now in full June rhythm, offering hop on, hop off access to tasting rooms, vineyards, and downtown shops. With Oregon Wine Month just behind us, June keeps the momentum going with warm evenings, patio tastings, and scenic rides through the historic Jacksonville Wine District. Whether you are a first-time visitor or a longtime local, there is something magical about watching our picturesque valley roll by from a trolley window.

June also brings a lineup of celebrations that highlight Jacksonville at its best. Complementary history trolley tours for graduates during the first week of the month, including fathers during Father’s Day weekend, while families fill the town for outdoor dining, live music, and early summer events. Our boutiques, galleries, and cafés are buzzing, and the Britt season kicks off with a great lineup of concerts—adding even more energy to weekends downtown.

Experience the charm of Jacksonville with a stay that is as unique as the town itself. Whether you are looking for a cozy bed and breakfast, a historic inn, or a luxury boutique hotel, Jacksonville offers a variety of accommodations that blend comfort with local flair.

As we celebrate the start of summer, I am reminded how fortunate we are to live in a place where history, culture, and community come together so naturally. Our trolleys are a symbol of that spirit—connecting people, supporting local businesses, and offering memorable experiences all season long.

Here’s to a vibrant June in historic Jacksonville. I hope to see you on board.