If you can’t find something fun to do around Maryland this May, you’re not looking in the right places. We get that everyone has busy schedules, so we’ve taken some of the work out of it with this list of can’t-miss events you should check out.
There’s plenty going on during Memorial Day Weekend, which falls on May 23-25, this year, but farmers markets and spring festivals are starting, local musicians are performing and numerous patriotic, veterans and Preakness events are planned for the month.
- May 9 - Mother's Day Weekend at Harford Vineyard & Winery, Jarrettsville
- May 9 - 2026 Harford Choral Society Annual Spring Concert, Bel Air
- May 11-13 - Freedom Truck, Bel Air
- May 14 - Howard County Veterans Monument Opening and Dedication, Columbia
- May 14 - Hunt Valley Chorale Free Spring Concert Series, Columbia
- May 16 - The International Gem & Jewelry Show, Timonium
- May 16 - Relay for Life, Columbia
- May 16 - Aberdeen Porch Fest, Aberdeen
- May 16 - 17th Annual Gaithersburg Book Festival
- May 16 - 20th Annual Secret Garden Tour, Havre de Grace
- May 16 - Paws in the Park, Gaithersburg
- May 16 - Chesapeake Chorale Concert, Bowie
- May 17 - A Tribute to the Piano Men, Columbia
- May 17 - Third Annual Taste of Harford, Havre de Grace
- May 17 - Goat Yoga, Woodstock
- May 17 - 4th Annual Charity Pickleball Tournament, Gaithersburg
- May 22 - Flags For Our Heroes, Gaithersburg
- May 23 - 2026 Classic Car Cruise Night, Jarrettsville
- May 24 - Memorial Day Weekend Shake Up, Rockville
- May 29 - Boys & Girls Clubs of Harford & Cecil Counties Scaveganza, across Harford and Cecil counties
- May 30 - 2026 Autism Family Fun Fest, Aberdeen
- May 30 - Savor the Magic of Greece Cooking Class, Ellicott City
- May 31 - OhanaHC 5K & 1 Mile Fun Run & Walk, Columbia
- May 31 - World Heritage Festival, Silver Spring
- Saturdays - Farmer's Market, College Park
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