My View – May 2026

IT’S MAY… and that means it’s trolley season in our historic landmark town. For decades, Jacksonville’s iconic trolley has been a familiar site in the warmer months. But did you know the Chamber of Commerce now operates three trolleys and that a fourth is rumored to be in the works? The reason for the growth is that trolleys provide a fun, unique way to see town on a year-round basis and provide a memorable way to experience Jacksonville like no other. In the beginning, the trolley tours were exclusively historic tours—shuttling passengers on a loop around town with a knowledgeable driver and docent who know their history and are masters at pointing out historic properties and telling tales of our once gold-rich town.

Today, the new wine trolleys and holiday light trolleys have expanded the program from history to wine and seasonal celebrations. On May 1, The Chamber of Commerce launches another season of its popular wine trolley tours, a hop-on, hop-off service that enables wine tasters to visit several wineries on the route while immersing themselves in wine and nostalgia at once!

Presently, the Chamber employes five trolley drivers and is looking to hire two more—interested drivers should contact the Chamber of Commerce for more. On this month’s cover, we’re excited to bring you an image of a familiar local resident—Brian Roberts—the longest-tenured driver who’s celebrating 15 years as a trolley driver this month. Help celebrate this milestone by thanking Brian with a wave when he passes by you on the street!

Once again, town is humming this month with loads of events and activities, including the historic and wine trolley tours, plus the Jacksonville Wine Cruise, the Applegate Valley Uncorked Wine Tour, a Wildfire Preparedness Day, Friday Art Rush, the Rotary Club Cork & Fork fundraiser, Historic Jacksonville’s Then & Now event…and lots more fun and interesting things to do in Our Small Town with Big Atmosphere!

Featured image: Jacksonville Trolley Driver, Brian Roberts. Photo: Tony Kay Photography