- Our list of the best things to do in Middletown, Maryland, features the top 219 nearby activities — including 77 great attractions with user approval ratings of 90% or more!
- Middletown, MD has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Entertainment & Shows, Sights & Landmarks, and Museums & Galleries.
- The results below include the top 3 things to do within the city of Middletown, MD , followed by 216 popular activities in nearby cities, including Hagerstown, Frederick, Leesburg, Martinsburg, Purcellville, Harpers Ferry, Mount Airy, Thurmont, Germantown, Charles Town, Sharpsburg, Emmitsburg, Shepherdstown, Boonsboro, New Market, Knoxville, Lovettsville, Gaithersburg and Berkeley Springs
Showing 121-130 of
957
18.1 Miles
Wine tastings are the main focus of Fabbioli Cellars, but they also allow for self-guided tours of the vineyards. Guests must first reserve an appointment if they wish to visit the fields themselves instead of simply having a tasting.
18.1 Miles
Featuring laser- and sound-enhanced cosmic bowling in the evenings, Shenandoah Lanes offers open bowling and league play. The alley also offers lightweight balls for younger bowlers, and has a bar and grill on the premises.
18.2 Miles
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0 votes
Flowing Springs Road, Charles Town, WV 25414
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The Jefferson County Little League provides organized leagues for children from ages 6 through 14. Leagues include t-ball for young players, as well as baseball and softball coached under adult supervision at all times.
18.4 Miles
Visitors can enjoy a diverse collection white, red, and dessert wines at Doukenie Winery. The winery hosts tastings, tours, and other special events and has won numerous awards for their wines.
18.8 Miles
83%
109 votes
13601 Glissans Mill Road, Mount Airy, MD 21771
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Linganore Winecellars is a winery located at northeast of historic New Market. They have a winetasting room, banquet hall, and a 40-acre vineyard for touring. They offer fruit wines, white wines, red wines, and more.
18.8 Miles
83%
109 votes
13601 Glissans Mill Road, Mount Airy, MD 21771
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Linganore Winecellars makes and sells a wide variety of wines, including reds, whites, and fruit wines. They host themed tastings and food pairings, as well as festivals and special events.
18.9 Miles
45%
924 votes
750 Hollywood Drive, Charles Town, WV 25414
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Hollywood Casino at Charles Town Races offers 98 game tables, including tables for blackjack, craps, roulette, min-baccarat, Pai Gow Poker. The casino also has 3,200 slot machines and 26 poker tables.
19.3 Miles
95%
103 votes
16300 Old Emmitsburg Road, Emmitsburg, MD 21727
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The National Shrine Grotto of Our Lady of Lourdes, dating back to late 19th century, is one of the oldest surviving American replicas of the French shrine and is surrounded by beautiful gardens.
19.4 Miles
85%
55 votes
37938 Charles Town Pike, Purcellville, VA 20132
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Part of the Waterford Cluster of wineries, Crushed Cellars Winery offers Chardonnay, Vidal Blanc and Meritage wines. The winery offers wine tastings as well as snacks including local cheeses, fresh baked breads and dips.
19.4 Miles
60%
154 votes
36716 Charles Town Pike, Purcellville, VA 20132
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The French countryside is brought to life at the Hillsborough Vineyards with lush rolling hills and stone barns providing the backdrop for their tasting room. Visitors can have casual tastings daily April through December.