United States · Wine Travel
Maryland wine festivals & events
227 listings / 48 festivals / 179 events / peak may–june
Showing 25–48 of 168 events
Upcoming onlyFilters
May 20, 2026 · Annapolis, MD
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
$20–$40
View details
May 27, 2026 · Baltimore, MD
Sips of Summer Series: #2 Kaapzicht Wines of South Africa
$25
View details
May 28, 2026 · Chestertown, MD
Grape Expectations: Brampton 1860 “Mexico Reimagined”
$85
View details
July 29, 2026 · Frederick, MD
Wine Down Wednesday: An Elevated LGBTQ+ Social | Happy Hour, Wine, Italian
Free
View details
Newsletter
Join The Pour
Get the best upcoming wine festivals, seasonal picks, and planning guides in your inbox each week.
No spam. Unsubscribe anytime.