Maryland Wine Festivals 2026: The Locals List for Wine, Music, Food, and Fun

One thing about Maryland is we have some of the most amazing wine 🍷 festivals from R&B to Caribbean to Upscale Luxury vibes. These festivals are even great for those who don’t love wine as many have music, performances, art, food and fun.

👯 Going with friends? Don’t worry about driving and trying to find parking…take The Black Bus instead. They now have karaoke so you can sing on your way to and from there!

Get 10% off when you book by July 15th if you mention you saw it in @ItsSomewhereLocal Newsletter

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Wine on the Water is that vibe…. and I try to go every year. Right in Middle Branch park, it’s on the water with a backdrop of the city skyline…the perfect way to spend a day in Baltimore.

Here’s the full list for 2026 Wine Festivals happening

(Bookmark and come back as I update the list if I find new ones)

4/25 DC Wine Fest – DC

4/26 The 20th Anniversary Highlandtown Wine Festival – Baltimore

5/2 Art Wine Festival – Sykesville, MD

5/7-31 Wine Village – Baltimore

5/10 Secret Garden Jazz Music Arts and Wine Festival – Westminster, MD

5/16-17 Wine in the Woods – Columbia MD

5/21 Wine at Sunset Patterson Park – Baltimore

5/23-24 Caribbean Wine & Music Festival – MT Airy, MD (Linganore)

5/30 Wine Art and Music Fest – Taneytown, MD

6/6 Maryland Wine Festival – Carroll Co, MD

6/7 Wine on the Water – Baltimore

6/13 Wine & Food Fest – Timonium, MD

6/13 Maryland Craft Spirits Festival – Frederick, MD

6/13 4 The Cool in You Wine & Music Festival – Ft Washington, MD

6/13 Fest of Spring – Baltimore

6/18-19 Sweet Escapes Wine Fest – Mt Airy, MD

6/20 Wine and Music Festival – Boonsboro, MD

6/21 Afro Soca Wine Food & Music Fest – Anne Arundel Co Fair, MD

6/27 Secret Garden Jazz Music Arts and Wine Festival – Westminster, MD

7/5 Rhythm & Wine Festival – Baltimore

7/5 Afro Beats & Wine – DC

7/19 Secret Garden Jazz Music Arts and Wine Festival – Westminster, MD

8/1 Caribbean Wine Splash – Rising Sun, MD

8/1 Caribbean Trio Fest – Charles County, MD

8/8 9th Annual Arts, Wine, Jazz & Soul Festival – Havre De Grace, MD

8/8 Wine and Slow Jams – Oxon Hill, MD

9/11-12 Deep Creek Lake Art, Wine & Spirits Fest – McHenry, MD

9/19 Susquehanna Wine & Seafood Fest – Havre De Grace, MD

9/26 Harford Co Wine Festival – Bel Air, MD

9/26 Unwine Festival – Upper Marlboro, MD

10/10 Wine on the Shrine – Ellicott City, MD

10/10-11 Autumn Reggae Festival – Mt Airy, MD

10/17 DC Wine Fest (Fall Edition) – DC

10/17 The Wine Festival in Kurtz Beach – Pasadena, MD

10/23-24 Wine on the Beach – Ocean City, MD

10/2026 TBD Wiskey, Wine & Fire – Timonium, MD

10/31-11/1 Fall Back Ciders, Spirits & Wine Fest – Boonsboro, MD

11/7 Secret Garden Jazz Music Arts and Wine Festival – Westminster, MD