The 5 Best Trivia Locations Around Frederick

A little friendly competition can turn an ordinary evening into a lively gathering of friends, neighbors and fellow trivia enthusiasts. Throughout Frederick County, Maryland, restaurants, breweries and entertainment venues host trivia nights that challenge participants with questions about history, sports, entertainment, science and popular culture. Whether competing for prizes, testing obscure knowledge or simply enjoying a night out, teams can find welcoming settings that combine mental challenges with food, drinks and conversation. The Best of the Best recognizes trivia locations in the Frederick area that bring people together for entertaining evenings of questions, answers and friendly rivalry.

Springfield Manor Winery Distillery Brewery

Springfield Manor Winery Distillery Brewery combines Friday evening trivia with the scenic surroundings of its historic 130-acre estate near Thurmont, offering participants a distinctive setting for friendly competition. Teams can register beginning at 6:30 p.m. before the games run from 7 to 9 p.m., with prizes, visiting food trucks and opportunities for individuals to join other players. Guests can enjoy estate-produced wines, craft beers and distilled spirits, including bourbon made with farm-grown corn and the property's signature lavender gin, while competing in the winery's indoor and outdoor gathering spaces.

10Tavern

10Tavern brings a modern, family-friendly sports bar atmosphere to Thurmont, combining classic American food, drinks and community entertainment in a renovated downtown setting. Its events calendar includes recurring trivia activities, giving friends and families opportunities to gather for friendly competition while enjoying burgers, sandwiches and other tavern favorites. A rotating draft selection features local IPAs, craft beers and familiar domestic offerings, while happy hour specials and numerous televisions contribute to the restaurant's lively social atmosphere.

Steinhardt Brewing

Founded by Jim and Daria Steinhardt, Steinhardt Brewing offers a downtown Frederick trivia destination centered on traditional Belgian and German-style craft beers. Its Thursday evening Pour House Trivia events typically run from 7 to 9 p.m., inviting teams to test their knowledge while enjoying the brewery's spacious tasting rooms and welcoming atmosphere. Beyond trivia, the brewery maintains an active entertainment calendar featuring live music, bluegrass gatherings, jazz performances and other community activities, making it a destination for social outings throughout the week.

Anchor Bar

Known as the birthplace of the original Buffalo chicken wing in 1964, Anchor Bar brings its longstanding restaurant tradition to Frederick through a sports bar atmosphere that combines casual dining with entertainment. Its local events calendar features trivia competitions, including Tuesday evening games, alongside music bingo, live performances and themed activities that encourage guests to gather beyond traditional mealtimes. Participants can enjoy the restaurant's signature Buffalo wings, pizzas, burgers and other American favorites while taking advantage of weekday lunch specials, happy hour offerings and rotating promotions.

Belles' Sports Bar & Grill

A Frederick dining and entertainment destination since 1992, Belles' Sports Bar & Grill combines casual American cuisine with a variety of games and organized competitions. Its free Pour House Trivia nights take place Wednesdays at 7 p.m. and Saturdays at 6:30 p.m., welcoming teams for an evening of questions and friendly competition in a locally owned establishment. Guests can choose from 20 draft beers and a menu featuring crab cake sandwiches, ribs and flatbread pizzas, while additional activities include billiards leagues, darts, cornhole and World Tavern Poker.

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