August 8, 2026 · Fort Washington, MD
Wine and Slow Jams: The Ultimate R&B Festival
$75–$95
View detailsUnited States · Wine Travel
Maryland wine festivals & events
227 listings / 48 festivals / 179 events / peak may–june
Showing 25–48 of 48 festivals
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August 9, 2026 · Crownsville, MD
DMV Summer R&B Wine, Food & Music Festival Vendor Sign Up
$200–$500
View detailsAugust 23, 2026 · Westminster, MD
SECRET GARDEN SUMMER FINALE REGGAE / GO-GO MUSIC, ARTS, and WINE FESTIVAL
$20–$40
View detailsSeptember 13, 2026 · Baltimore, MD
Wine on the Water Baltimore
$40; reserved tents $600–$650
View detailsgroups · couples
September 19, 2026 · Havre de Grace, MD
Susquehanna Wine & Seafood Fest
$15–$20 entry only; $40–$50 tasting ticket; $85–$95 VIP
View detailsfoodies · groups
September 26, 2026 · Bel Air, MD
Harford County Wine Festival
$60 GA, $140 VIP; Wine Enthusiast and designated-driver tiers
View detailsgroups · couples
October 4, 2026 · Westminster, MD
Secret Garden Autumn R&B Music, Arts and Wine Festival
$20–$40
View detailsgroups · couples
October 4, 2026 · Westminster, MD
SECRET GARDEN AUTUMN RNB MUSIC, ARTS and WINE FESTIVAL - ALL OLD SCHOOL
$20–$40
View detailsOctober 31, 2026 · Boonsboro, MD
Fall Back Hallo-Wine Fest
$41–$59 by entry time; $23 non-drinker
View detailsgroups · couples
November 7, 2026 · Westminster, MD
Secret Garden Funk, Soul and Trailride Music, Arts and Wine Festival
$20–$40
View detailsgroups · couples
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