August 8, 2026 · Fort Washington, MD
Wine and Slow Jams: The Ultimate R&B Festival
$75–$95
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United States · Wine Travel
Maryland wine festivals & events
176 listings / 51 festivals / 125 events / peak may–june
Showing 25–48 of 51 festivals
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August 9, 2026 · Crownsville, MD
DMV Summer R&B Wine, Food & Music Festival Vendor Sign Up
$200–$500
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August 23, 2026 · Westminster, MD
SECRET GARDEN SUMMER FINALE REGGAE / GO-GO MUSIC, ARTS, and WINE FESTIVAL
$20–$40
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September 5–6, 2026 · Fort Washington, MD
2026 Wine Down Summer Music Festival
$70–$250
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September 13, 2026 · Baltimore, MD
Wine On The Water (R&B & Neo Soul) Wine & Arts Festival
$40–$650
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September 17, 2026 · Chestertown, MD
Grape Expectations: Brampton 1860 “Harvest Afterglow: A Late Summer Supper”
$85
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September 19, 2026 · Havre de Grace, MD
6th Annual Susquehanna Wine & Seafood Fest
$15–$125
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October 4, 2026 · Westminster, MD
SECRET GARDEN AUTUMN RNB MUSIC, ARTS and WINE FESTIVAL
$20–$40
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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 31, 2026 · Boonsboro, MD
Fall Back Hallo-Wine Fest 2026 Sponsorship Registration
$300–$500
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October 31, 2026 · Boonsboro, MD
Fall Back Hallo-Wine Fest 2026 Vendor APPLICATION
Free
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November 7, 2026 · Westminster, MD
SECRET GARDEN FUNK, SOUL, and TRAILRIDE MUSIC, ARTS and WINE FESTIVAL
$20–$40
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