2026 Maryland Wine Festival List

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.

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

6/6 5th Annual Reisterstown Beer & Wine Festival - Reisterstown, MD

6/7 Wine on the Water - Baltimore

6/13 Wine & Food Fest - Timonium, MD

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

6/13 Fest of Spring - Baltimore

6/14 Sunset in the Garden Wine Fest - DC

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

6/20 Wine and Music Festival - Boonsboro, MD

6/20 DMV RnB Wine Fest - Anne Arundel Co Fair, 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 (Pretty Ricky, Donnell Jones, Case)

8/8 Island in the Park Wine, Food and Music Festival - Anne Arundel Co Fairground

8/9 DMV Summer R&B Wine Food and Music Festival - Anne Arundel Co Fairground

8/14-16 HopFest at Max Taphouse - Baltimore, MD

8/23 The Roost South African Wine Fest - DC

9/5 Black Food + Wine Festival - DC

9/13 Wine on the Water - Baltimore, MD

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

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

9/25-26 Rhythm & Blues at Hennessy Creek - Brandywine, 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

FYI: I will update this list as I find new ones so bookmark this page or if you are clicking on the email, just come back and hit the read on web button in the top right corner for the updated version.

If you found something helpful, fun, or worth trying — forward this to a friend who always says “there’s nothing to do around here.”

And if you want these ideas showing up in your inbox every week…

You already know where to be 😉

Talk next week,
Lisa

P.S. Do you have an event or idea you want me to cover? Hit reply. I read every one.

See you ——-Somewhere!

Disclaimer: I do not host any of these events or have any affiliation with them.

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