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5 Things to Do in Annapolis This Weekend (June 2-4, 2023)

By Darla Winstead - Publisher of Macaroni Kid Annapolis June 1, 2023

Looking for something fun to do with your family over the weekend? Macaroni KID Annapolis has you covered? While there are many family-friendly events and activities happening in the Annapolis area, we've rounded up our top suggestions to help make your weekend planning a bit easier. Click on the title for more information. The events are local or worth the drive.*


Bowie BAYSOX Home Games

  • What: Watch a minor league baseball game with your family. Giveaway, special themes, food, and fun for the entire family.
  • When: 
    • Friday, June 2, 7:05-10:05 (90's Night with Fanny Pack giveaway)
    • Saturday, June 3, 6:35-9:35pm (Star Wars Night and Fireworks)
    • Sunday, June 4, 1:05-4:05pm (Bobblehead giveaway, Autographs, and Run the bases after the game)
  • Who: All Ages
  • Where: Prince George's Stadium - Home of the Bowie Baysox, 4101 Crain Hwy, Bowie
  • Fee: Starts at $10

Cape St. Claire Strawberry Festival

  • What: A strawberry themed event starting with a parade at 10am. There will be live music (7 bands), food and beverages (Beer Garden), games, vendors, petting zoo, face painting, variety of activities for all ages and strawberries in many forms.
  • When: Saturday, June 3, 10am - 7pm - Parade starts at 10am
  • Who: All Ages
  • Where: Cape St. Claire Main Beach, 1223 River Bay Rd, Annapolis
  • Fee: Free  

Annapolis Greek Festival

  • What: There will be Greek Food, Greek Music, Greek Pastries, Greek Dancing, Beer/Wine and Vendors! 
  • When: Saturday, June 3, 11am - 9pm and Sunday, June 4, 11am - 7pm
  • Who: All Ages
  • Where: Sts. Constantine & Helen Greek Orthodox, 2747 Riva Road, Annapolis
  • Fee: Free to enter 

Annapolis Pride Parade and Festival

  • What: The half-mile parade will take place on June 3rd and step off at noon at the intersection of Amos Garrett Blvd. and West Street. The parade continues along West Street (toward downtown) then takes a left on Calvert Street where the festival will occur. Nearly 100 groups are expected to participate in the parade. More than 100 artisans, businesses and community organizations will have tables in the People’s Park, West Street, between Calvert Street and Church Circle and adjacent parking lots. Talented artisans and LGBTQIA+ supporting organizations will also be on site providing information, giving out swag and selling hand-crafted and special merchandise. Food and beverages will be for sell.    
  • When: Saturday, June 3, Noon -5pm  
  • Who: All Ages
  • Where: West Street, Downtown Annapolis
  • Fee: Free

First Sunday Arts Festival

  • What: Spend some time in historic Annapolis during this monthly street festival. Shop from over 100 artisans and vendors. Watch live entertainment and enjoy food from area restaurants. 
  • When: Sunday, June 4, 11am - 5pm
  • Who: All Ages
  • Where: First block of West Street from Church Circle, Annapolis
  • Fee: Free  


Have a MacKIDtastic Week!


*Publishers Note: This page is updated each week. Top picks are merely suggestions based on a variety of interests suitable for a wide demographic of families. We encourage parents and caregivers to use their own judgement when choosing events to attend. From time to time, events may be canceled or postponed without notice. Be sure to double-check with the venues to make sure the event is still scheduled.