2025 is packed with fantastic wine festivals throughout Maryland and Pennsylvania, and we’ve got a list of the best ones coming your way!
April 26 – Westminster Wine Stroll
Downtown Westminster, MD
The Westminster Wine Stroll invites you to Sip, Shop & Stroll through Main Street, which transforms into a vibrant Wine Mart with local wineries, wine-related vendors, and food offerings from local establishments. Enjoy live entertainment from Weird Science while you explore all that this local event has to offer.
May 3 – Sykesville Art & Wine Festival
Downtown Sykesville, MD
This charming festival brings together exciting wine samples from some of the best wineries in Maryland, Sonoma Valley, Argentina, France, and Italy. You’ll also enjoy live entertainment, local artists, and food from small-town vendors. With your collectible Sykesville glass, you’ll have unlimited access to wines including whites, reds, rosés, cavas, and other specialty varieties.
May 3 – June 1 – Wine Village in Baltimore
West Shore Park, Inner Harbor, Baltimore, MD
Baltimore’s Inner Harbor will host Wine Village, an exciting new wine festival modeled after traditional European wine events. Enjoy a curated selection of local and international wines, along with non-alcoholic beverages, beer, and cocktails. You can also shop from arts & crafts vendors, indulge in European-inspired food, and enjoy live performances and family-friendly activities like movie nights and carousel rides.
May 24-25 – Caribbean Wine & Music Festival
Linganore Winecellars, Mount Airy, MD
Celebrate island vibes at Linganore Winecellars with their Caribbean Wine & Music Festival. Known for hosting the longest-running reggae festival on the East Coast, Linganore brings together reggae music, island cuisine, local artisan vendors, and unlimited wine sampling from their own vineyards. Don’t miss out on this vibrant festival!
June 14 – Wine & Food Festival
Timonium Fairgrounds, Lutherville-Timonium, MD
The Wine & Food Festival offers a massive selection of over 100 wines to sample, including local Maryland wineries, international varieties from Italy, France, and Spain, and domestic wines from California and Virginia. In addition to wine, enjoy a fantastic lineup of regional live music, local food trucks, and beer and seltzer options. The event also includes a special VIP experience with an exclusive lounge, extra sampling time, and more.
July 19-20 – Summer Soca Wine & Music Festival
Linganore Winecellars, Mount Airy, MD
Back at Linganore Winecellars, the Summer Soca Wine & Music Festival brings an exciting blend of wine, music, and Caribbean vibes. This festival promises to deliver a vibrant mix of great wine and live soca music, offering another unique experience at this scenic venue.
Sept 6-7 – Gettysburg Wine & Music Festival
Granite Hill Camping Resort, Gettysburg, PA
Head to Gettysburg for a weekend of wine, spirits, and music at this lively festival. With over 100 wines from top Pennsylvania wineries, along with crafted spirits from local distilleries, this event offers plenty of opportunities to sip and shop while enjoying great live music in a beautiful, historic setting.
Sept 13 – 41st Maryland Wine Festival
Carroll County Farm Museum, Westminster, MD
This annual festival celebrates Maryland’s wine culture in a one-day event at the Carroll County Farm Museum. Visitors can explore a wide variety of local wines, shop from juried artisans, and enjoy live music in a picturesque farm setting. This is a great event for those who want to experience Maryland’s rich wine offerings in a relaxing, family-friendly environment.
Oct 11 – Wine at the Shrine Festival
Shrine of St. Anthony, Ellicott City, MD
Wine at the Shrine is not only a wine festival but also a community event benefitting two important organizations – Little Portion Farm and the Franciscan Center of Baltimore. In addition to wine and beer sampling, enjoy local food trucks, live music, hayrides, cooking demonstrations, farm tours, and kids’ activities, all set against the stunning backdrop of the Shrine of St. Anthony.
Oct 11-12 – Autumn Wine & Reggae Festival
Linganore Winecellars, Mount Airy, MD
Linganore Winecellars hosts another incredible event in October with their Autumn Wine & Reggae Festival. Expect great wine, reggae music, and the amazing autumn atmosphere at one of Maryland’s most scenic vineyards. Stay tuned for the lineup of artists and ticket information!
Oct 18 – 3rd Annual Whiskey, Wine & Fire
Maryland State Fairgrounds, Timonium, MD
A unique experience for those who appreciate whiskey, wine, and fiery culinary delights, this festival offers whiskey bars, wine tasting stations, and plenty of fire-kissed BBQ and open-fire cooking. Relax around firepits, enjoy live music, and indulge in fantastic pairings while surrounded by the excitement of fire breathers and other performances.
Whether you’re a wine connoisseur, a lover of live music, or just looking for a fun weekend outing, these festivals offer the perfect mix of flavor, entertainment, and community spirit. Each one provides a unique experience that’s sure to leave you with lasting memories.
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