United States · Wine Travel
Maryland wine festivals & events
92 listings / 37 festivals / 55 events / peak may–june
Showing 25–48 of 55 events
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May 15, 2026 · Westminster, MD
Sunset Sip n' Stretch at Serpent Ridge Vineyard
$30
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Groups · Foodies
May 20, 2026 · Annapolis, MD
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
$20–$40
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May 27, 2026 · Baltimore, MD
Sips of Summer Series: #2 Kaapzicht Wines of South Africa
$25
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May 28, 2026 · Chestertown, MD
Grape Expectations: Brampton 1860 “Mexico Reimagined”
$85
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