September 26, 2026 · Baltimore, MD
Love Story Mobile Winery: National wine day event
$18
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United States · Wine Travel
Maryland wine festivals & events
227 listings / 48 festivals / 179 events / peak may–june
Showing 121–144 of 168 events
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September 27, 2026 · Annapolis, MD
Great Frogs Wine Tasting to Benefit the Navy SEAL Foundation
$60
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October 3, 2026 · Baltimore, MD
SAVE THE DATE! CANTON WINE GIRL'S CHESAPEAKE WINE CO TURNS TWO!!
Free
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October 10, 2026 · Mount Airy, MD
Autumn Reggae Wine & Music Festival 2026 | Linganore Winecellars
$35–$99
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October 11, 2026 · Bethesda, MD
Wine Tasting: An Evening of Wine, Connection & Community
Free
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October 12, 2026 · Rockville, MD
FRONT OF HOUSE: The Psychology of Hospitality - Wine. Food. Hospitality.
$450
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October 12, 2026 · Rockville, MD
Points of view with Julia Coney, Andrew Elder, and Tom Sietsema.
$450
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October 15, 2026 · Chestertown, MD
Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper”
$85
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