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Maryland Events in May 2026

I can’t believe the weather is finally warming up and we can enjoy the lovely Spring weather. We just wrapped up the Cherry Blossom season and that was so beautiful to see. It is one of my favorite parts of Spring.

Anyway, with the months speeding through, here is your guide to the best events that will be taking place around Maryland in May 2026. Our hope is that you find lots of events and things to do to make memories with family and loved ones!

Maryland Events happening in May 2026 by Region

WESTERN MARYLAND (Mountains + Cumberland + Frederick County)

DelFest (Cumberland)

A major family-friendly bluegrass music festival with live performances, kids’ activities, food vendors, and camping options.

  • When: May 21–24
  • Time: 4pm daily
  • Where: Allegany County Fairgrounds
  • Cost: Ticketed event (multi-day and single-day passes available)

Maryland Iron Festival (Thurmont)

A historical festival celebrating Maryland’s iron-making heritage with blacksmith demos, crafts, and family activities.

  • When: May 16–17
  • Time: Saturday 10AM to 6PM  and Sunday 10AM to 4PM
  • Where: Catoctin Furnace
  • Cost: Free

Springfest (Brunswick)

A community festival with food vendors, live entertainment, local businesses, and family-friendly fun.

  • When: May 16
  • Time: 10am to 5pm
  • Where: Downtown Brunswick
  • Cost: Free

CENTRAL MARYLAND

Towsontown Spring Festival

A large outdoor festival with live music, food vendors, shopping, and activities for families.

Sykesville Art & Wine Festival

  • A relaxed arts festival featuring local artists, wine tastings, live music, and food.
  • When: May 2, 2026
  • Time: 12 to 4 pm
  • Where: Sykesville, MD
  • Cost: Varies

Oxford Fine Arts Festival

A waterfront arts festival with fine art displays, crafts, and live entertainment.

  • When: May 15–17, 2026
  • Time: Friday, May 15th, 6:00–8:00 PM, Saturday, May 16 (10 AM–5 PM) and Sunday, May 17 (10 AM–4 PM)
  • Where: Oxford, MD
  • Cost: $5

Kid’s Fishing Rodeo

A fun, beginner-friendly fishing event designed for kids with prizes and guided support.

  • When: May 17, 2026
  • Time: 8am to noon
  • Where: Krimgold Park
  • Cost: Free

This event is for kids age 15 and under.

Artscape

One of the largest arts festivals in the U.S. with performances, art exhibits, food, and family activities.

  • When: May 23–24, 2026
  • Time: 11AM – 10PM
  • Where: Baltimore, MD
  • Cost: Free

EASTERN SHORE

Chesapeake Bay Sailing & Wine Experiences

Scenic boat cruises paired with wine tasting experiences along the Chesapeake Bay, great for a relaxed family or date outing.

Chesapeake Beach Stars & Stripes Festival

A Memorial Day celebration with live music, food vendors, and fireworks.

  • When: Memorial Day weekend
  • Time: Evening (fireworks at night)
  • Where: Chesapeake Beach, MD
  • Cost: Free

CAPITAL REGION

Maryland Plant Festival

A vibrant plant and lifestyle festival featuring plant vendors, food trucks, and live music.

  • When: May 23–25, 2026
  • Time: Daytime
  • Where: Silver Spring, MD
  • Cost: Ticketed or free entry depending on day

Puerto Rico in Maryland Festival

A cultural festival celebrating Puerto Rican heritage with music, dancing, and authentic food.

  • When: May 30, 2026
  • Time: 12pm to 6pm
  • Where: Sandy Spring, MD
  • Cost: Free

Columbia Mother’s Day Marketplace

A shopping-focused event with local vendors, gifts, and family-friendly activities.

  • When: May 8–10, 2026
  • Time: Daytime
  • Where: Columbia, MD
  • Cost: Free

SOUTHERN MARYLAND

Calvert Arts Festival

A local arts festival featuring artists, crafts, live entertainment, and food vendors.

  • When: May 9, 2026
  • Time: 10 to 5pm
  • Where: Sunderland, MD
  • Cost: Free

STATEWIDE / SEASONAL

Strawberry Festivals & Pick-Your-Own Farms

Check out our strawberry picking blog post for full details.

Seasonal strawberry picking events with family activities like hayrides, petting zoos, and fresh food.

  • When: Mid–late May 2026
  • Time: Varies by farm
  • Where: Various farms across Maryland
  • Cost: Pay-per-entry or pay-per-pound

Carnivals happening in May 2026 all around Maryland

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Lola lives in Maryland and is the founder of Deyewa where she helps families discover kid and family friendly areas in Maryland with printables, tips, guides and ideas to help families have the best experiences. She is a wife and mom to 3 amazing kids and loves to spend time exploring Maryland and surrounding states with them. When she is not blogging or at her day job, she enjoys traveling, going to kids' activities in Maryland, church and eating out.