LEONARDTOWN, Md. — Three of Leonardtown’s most popular hangouts are joining forces to welcome fall in the best way possible — with pints, cocktails, and plenty of local flavor. The 2025 Leonardtown Square Fall Bar Crawl takes over downtown on Friday, Oct. 10, running from 12 p.m. until last call.
Olde Town Pub, Social Coffeehouse, and The Rex are teaming up for this year’s event, inviting guests to sip, snack, and stroll between locations throughout the day. Participants can pick up a Fall Crawl Passport at any of the three venues with the purchase of food or a drink. Once they’ve collected stamps from each stop, crawlers can turn in their completed passport to score limited-edition bar crawl swag, available while supplies last.
Each location plans to bring its own twist to the fall festivities. Olde Town Pub will showcase local brews and hearty pub fare, The Rex will feature its signature cocktails and upscale bites, and Social Coffeehouse will transition from cozy café to late-night lounge as the evening unfolds.
Event organizers describe the crawl as a laid-back celebration of community and local business, offering an easy way to explore Leonardtown’s downtown scene and toast to the season. Drink specials and entertainment are expected to pop up throughout the day, giving participants a fresh reason to linger at every stop.
With crisp weather, good company, and the charm of historic Leonardtown as the backdrop, the Fall Bar Crawl promises to deliver a perfect mix of small-town spirit and big fall energy. Participants must be 21 or older and are encouraged to drink responsibly.
More information is available on the Leonardtown Square Fall Bar Crawl event page.
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