United States · Wine Travel
Maryland wine festivals & events
227 listings / 48 festivals / 179 events / peak may–june
Showing 1–24 of 36 upcoming events
Include 132 already heldFilters
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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October 17, 2026 · Westminster, MD
SIP NOW, TRAVEL LATER A Self-Care + Travel Experience
$80–$90
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October 18, 2026 · Baltimore, MD
FALL INTO CAKING: A Sip & Cake Decorating Experience
$85
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October 22, 2026 · Dickerson, MD
Hands-On Korean BBQ Cooking Class at Sugarloaf Mountain Vineyard
$65
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October 24, 2026 · Parkville, MD
Boo's & Booze—The Ultimate Halloween Wine Exchange
$10
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