Hagerstown Set to Host Diverse May and June Events Featuring Art, Music, and Family Fun

Residents of Hagerstown, Maryland, can look forward to a vibrant schedule of community events throughout May and early June, as announced by Downtown Hagerstown and the City of Hagerstown. The upcoming calendar features a variety of activities designed to engage families, art enthusiasts, and music lovers, ranging from outdoor art walks and a unique “Touch a Truck” event to a neighborhood music festival and a culinary competition. These events aim to foster community spirit and highlight the cultural offerings within the downtown area.

Kicking off the season on Saturday, May 9, 2026, is the “Art Walk” in downtown Hagerstown, running from 10:00 a.m. to 2:00 p.m. This event, hosted by Downtown Hagerstown & A&E District, will include walking tours of the Cultural Trail at 10:30 a.m. and 12:30 p.m. Attendees can also explore an artisan marketplace at University Plaza, enjoy caricature drawings at Potomac Walk, and participate in a coloring station at The Maryland Theatre. On the same day, from 10:00 a.m. to 2:00 p.m., the City Park Train Hub will host “Touch a Truck & Train,” an event organized by Hagerstown Parks & Recreation. This free, family-friendly activity will allow children to explore various trucks, trains, and equipment, and will also feature music, face painting, and balloons.

The following Saturday, May 16, 2026, brings “Porchfest” to South Prospect Street from 11:00 a.m. to 4:00 p.m., sponsored by the City of Hagerstown. This event promises free live music performed on the front porches of homes in the neighborhood. Later that day, from 3:00 p.m. to 8:00 p.m., downtown Hagerstown will host its inaugural “Battle of the Cheesesteaks” in the Elizabeth Hager Parking Lot, an event organized by One Room Media and sponsored by the City of Hagerstown. Ten vendors will be participating, allowing attendees to vote for the People’s Choice winner. Limited VIP tickets will be available, offering a meet-and-greet opportunity with “The Cheesesteak Guy.”

The end of May will see the grand opening of the 2026 City Farmers Market season on Sunday, May 31, 2026, held at Hub City Brewery, located at 25 W Church St. The market will run from 11:00 a.m. to 3:00 p.m. and will offer fresh produce and goods from local vendors. This market will also return on Sunday, June 7, 2026, at the same location and time.

Concluding the initial series of events is the return of the iconic Western Maryland Blues Fest on Saturday, June 6, and Sunday, June 7, 2026, at Hub City Brewery. Hub City Brewery is taking the reins for this year’s festival, promising to bring major blues artists to Hagerstown. Ticket information for the Blues Fest can be found online.

Downtown Hagerstown, a Maryland Main Street Community, is dedicated to creating a thriving downtown environment. For inquiries about any of these events or to get involved with Downtown Hagerstown, individuals can contact events@downtownhagerstown.org.

Article by Mel Anara, based upon information from Downtown Hagerstown and the City of Hagerstown.

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