A Personal Note

Four days off, and my kids have already asked "what are we doing" eleven times. Just hope it stays warmish and dryish for Artscape and other events. I'd say outside of Artscape surrounding areas have a bit more going on this weekend than in town.

Top Pick

Artscape 2026 in Downtown Baltimore Saturday, all day | All ages | FREE

Baltimore's biggest free arts festival is back. Live music, interactive installations, street food from a dozen local vendors, and family programming running all morning. If your kids are old enough to people-watch and eat things on sticks, this is the day.

Why it's cool: Three hundred thousand people will be here this weekend. Nothing else competes on Saturday.

More info

Quick Weekend Wins

Just show up

Sunday Power Combo: Fam Jam → Pearlstone Strawberry Festival The strongest same-day pairing we've seen in a while. Fam Jam at Manor Mill runs 10-11am ($5/person), a one-hour family concert in a beautiful historic mill. Then drive 15 minutes to Pearlstone for opening weekend of strawberry season: organic U-pick berries (~$6/pound), a Kids' Corner, and a live concert. Full day, under $55 for the family. Sunday | Fam Jam 10-11am, Pearlstone 10am-4pm
Memorial Day Parade in Downtown Annapolis Flags, bands, something to point at. The waterfront parade is a spectacle for every age, and Annapolis makes a great lunch extension afterward. Monday | FREE
Fort McHenry Living History Civil War reenactors, ranger-led walks through the Star Fort, and flag ceremonies all weekend. Monday has the lightest crowds and a noon flag-raising ceremony inside the fort. $15/adult, under 15 free. Sat-Mon, programs start 9am | Plan your visit

Ticketed This Weekend

These need tickets

SkyZone Red, White & Blue Glow (Sky Zone Gambrills). Patriotic glow jump with lasers and music. Sunday 7-9pm, ~$34/person. Best as a parent + older kids outing (~$102 for three). Not a toddler event.
Chesapeake Baysox Game (Prince George's Stadium). Minor league baseball on a Sunday evening. ~$12/person. The 10,000-seat stadium means foul ball possibilities, between-inning games calibrated for kids, and none of the major league sticker shock.

Budget-Friendly Free Picks

Walters Drop-in Art Making. Create flowers for a collaborative garden at one of the best free museums in the country. Saturday 10am-1pm. No reservation, stroller-friendly. Also your best rain backup this weekend.
Pirate Cove Family Fun Day. Sensory activities, crafts, face painting, and prizes every half hour. Sunday 2-5pm in Havre de Grace. Registration required.
Hatton-Regester Green Concert. Free outdoor concert on the B&A Trail in Severna Park. Sunday 4-6pm. Bring a blanket.

For Toddler Families

Sensory-Friendly Sunday at Robinson Nature Center. Designed for families with sensory-processing differences or autism spectrum. Quiet nature exploration, Sunday 9-10:30am, $5. One of the best programs in Howard County.
Little Learners Celebrate Memorial Day. Ages 3-5 with adult. Friday 10:30-11am at East Columbia Branch Library. FREE. Short, sweet, age-targeted.
Bunny Encounters at The Farmyard. Sunday 4-6pm, $9/person. Registration required. A calm post-nap afternoon add-on.

Tween-Approved

Open Recording Studio at Catonsville Library. A real recording studio where teens can make and record music with provided instruments. Monday (May 26), FREE. Ages 14+ or with adult. This is the kind of thing that only exists because a library decided to be cool.
B&O Railroad Museum Memorial Day Weekend. Special holiday programming Sat-Mon, 10am-4pm. The STEM engineering angle works for kids who want to climb into train cabs and understand how things move. Free lot on Poppleton St.

Mark Your Calendar

Coming up in the next few weeks

May 30: Weber's Strawberry Festival (ticketed, tends to sell out)
May 31: CTA Family Fun Day (check registration now)
June 1: Baltimore County Summer Camps registration opens

Local Intel

Maryland Zoo hosts a 21+ craft beer festival this weekend (Brew at the Zoo). Good get a babysitter plan. Check marylandzoo.org for daily programming times.

Rain in the forecast? The Walters Art Museum is always free, always open, never requires a reservation. B&O Railroad Museum works too, though the roundhouse runs cool so bring a layer.

Also This Weekend

8 more events that almost made the cut

Kalinka Dance Ensemble — Friday 7pm, Slayton House, FREE
Bowie Memorial Day Parade — Saturday 11am, FREE
Dancing Stories with Kalanidhi Dance — Saturday 2-3pm, FREE
Chalk Art at Savage Library — Saturday, FREE
Picture Book Launch Party — Saturday, FREE
Wicked screening at Wine Bin — Saturday evening
Family Feed at Eden Mill — Monday, FREE
Pikesville Farmers Market — Monday morning, FREE

Artscape Hits Town for Memorial Day