Hagerstown, MD – Downtown Hagerstown is set to illuminate the holiday season with a comprehensive lineup of events designed to bring cheer and community spirit to residents and visitors alike. From new winter attractions to cherished annual traditions, the city’s holiday calendar promises a variety of activities catering to families, shoppers, and those seeking festive entertainment. The season kicks off with the debut of DiamondFest and continues through New Year’s Eve with a collection of markets, tree lightings, and unique cultural experiences.
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The inaugural DiamondFest, a new family-friendly event, will transform Meritus Park into a winter wonderland starting Friday, November 21, 2025. This event is scheduled to run every Friday, Saturday, and Sunday through the holiday period. Following a visit to DiamondFest, attendees are encouraged to patronize downtown Hagerstown restaurants. Also on November 21, The Maryland Theatre will host Holly Fest, a free event featuring live performances from youth groups specializing in dance, singing, and instrumental music. Tickets for Holly Fest can be reserved in person at the theatre or by calling 301-790-2000.
The festive weekend continues on Saturday, November 22, with the Downtown Holiday Market on South Potomac Street from 2:00 p.m. to 6:30 p.m. This market will showcase over 30 artisan vendors offering handmade gifts, jewelry, décor, and seasonal treats. Later that day, the annual Downtown Tree Lighting ceremony will take place at Public Square from 5:00 p.m. to 6:00 p.m., an event that includes a visit from Santa Claus, free hot cocoa, bounce houses, and musical performances by the North Hagerstown High School band and a vocal ensemble.
The focus on supporting local businesses will be highlighted on Saturday, November 29, with Small Business Saturday in downtown Hagerstown. As a Neighborhood Champion, Downtown Hagerstown Main Street will be promoting deals and discounts at local shops. A special Holiday Pop-Up Shop will also be open at 6 N Potomac Street from 11:00 a.m. to 5:00 p.m. on this day, featuring handmade items from local vendors. Shoppers who spend $50 or more at a downtown retail store will receive a complimentary gift with proof of purchase.
December brings further celebrations, beginning with the City Park Tree Lighting on Friday, December 5, from 5:00 p.m. to 8:00 p.m. This event at Hagerstown City Park will feature donuts and hot chocolate, a petting zoo, vendors, and giveaways, with the tree lighting ceremony scheduled for 7:00 p.m. The following Saturday, December 6, visitors can experience a German Christmas at the Hager House with special tours offered at 10:00 a.m., noon, and 2:00 p.m. Tickets for these tours are $5 per person, with children 12 and under admitted for free. The Holiday Pop-Up Shop at 6 N Potomac Street will also be open from 11:00 a.m. to 5:00 p.m. on December 6.
The traditional German Christkindl Markt will be held on December 12 and 13 at 50 W Washington Street, featuring local artisans selling Christmas wares and imported German goods, along with traditional German food and Gluehwein. The market will be open from 3:00 p.m. to 8:00 p.m. on Friday, December 12, and from 10:00 a.m. to 4:00 p.m. on Saturday, December 13. A Holiday Pop-Up Shop will also be available on December 12 from 3:00 p.m. to 8:00 p.m.
On Friday, December 12, from 6:00 p.m. to 8:00 p.m., the Merry & Bright Bus Tour will offer a unique experience. A traditional double-decker bus from Great Britain will tour Hagerstown neighborhoods to showcase holiday lights. While tickets for this specific tour are sold out, residents are encouraged to decorate their homes along the route to contribute to the city’s festive ambiance.
The Holiday Cookie Crawl is scheduled for Saturday, December 13, from 11:00 a.m. to 4:00 p.m., involving various downtown businesses. This event is expected to include visits with Santa Claus at Create-a-Candle, free hot cocoa, bounce houses, and vendor shopping.
Additional German Christmas Tours will be available at the Hager House on December 20, with the same schedule and ticket prices as previous dates. The city’s holiday festivities will conclude with the Krumpe’s Donut Drop at Meritus Park on Wednesday, December 31, from 5:00 p.m. to 7:00 p.m. This free, family-friendly event will feature live music, a kid’s zone, and a special countdown drop at 6:59 p.m.
Downtown Hagerstown Main Street, a Maryland Main Street Community, is dedicated to fostering a vibrant downtown environment. For inquiries about these events or to get involved, interested parties can contact events@downtownhagerstown.org.
Article by Mel Anara, based upon information from a press release.
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