United States · Wine Travel
Maryland wine festivals & events
92 listings / 37 festivals / 55 events / peak may–june
Showing 1–24 of 37 festivals
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May 9, 2026 · Forest Hill, MD
Uncorked in Bloom: Mother's Day at Harford Winery
$30–$55
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May 10, 2026 · Westminster, MD
SECRET GARDEN SPRING FLOWER MOTHER'S DAY JAZZ MUSIC, ARTS AND WINE FESTIVAL
$20–$40
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May 23, 2026 · Mount Airy, MD
Caribbean Wine & Music Festival 2026 | Linganore Winecellars
$35–$60
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Beginners
June 7, 2026 · Baltimore, MD
Wine On The Water- Caribbean Wine & Arts Festival
$40
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Beginners
June 13, 2026 · Baltimore, MD
FEST Of SPRING 2026: Wine, Food & Music Festival
$20–$100
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Foodies
June 20, 2026 · Boonsboro, MD
Quad State Wine & Music Fest 2026 Sponsor Registration
$500–$2000
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Collectors
June 21, 2026 · Crownsville, MD
Afro - Soca Wine Music & Food Festival Vendor Sign Up
$200–$500
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June 27, 2026 · Westminster, MD
SECRET GARDEN RNB - Neo-SOUL MUSIC, ARTS and WINE FESTIVAL
$20–$40
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July 18, 2026 · Mount Airy, MD
Sweet Escape Festival 2026 | Linganore Winecellars Wine & Music Festival
$35–$99
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July 19, 2026 · Westminster, MD
SECRET GARDEN CARIBBEAN MUSIC, ARTS and WINE FESTIVAL
$20–$40
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August 8, 2026 · Havre de Grace, MD
9th Annual Arts, Wine, Jazz & Soul Festival
$50–$80
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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 19, 2026 · Havre de Grace, MD
6th Annual Susquehanna Wine & Seafood Fest
$15–$125
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