Festival
Events
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Paint Annapolis
Downtown Annapolis Annapolis, United StatesPaint Annapolis, hosted by MFA, is a unique painting event that brings thousands of artists and art lovers to Annapolis the first week of June, and puts international professional visual …
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Let’s Go! Music Festival
Anne Arundel County Fairgrounds 1450 Generals Highway, Crownsville, United StatesLet's Go! Music Festival is the official kickoff to summer in Maryland. Created by a brother-and-sister duo from Annapolis, Let’s Go! was built by music lovers, for music lovers—and is …
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Cape St. Claire Strawberry Festival
Cape St. Claire Fire Department 1411 Cape St Claire Rd, Annapolis, United StatesThe Strawberry Festival Committee is happy to announce the 2026 Strawberry Festival. On the first Saturday in June, there will be strawberries on the shortcake and music on stage! The …
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Kids ‘n’ Kaboodle
Chesapeake Children's Museum 25 Silopanna Rd, Annapolis, United StatesDon't miss Kids 'n' Kaboodle! Everything is free! Call or stop by CCM to get a free pass to ride Annapolis Transit to and from the event. Free food thanks …
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First Sunday Arts Festival
53 West Street 53 West Street, Annapolis, United States +1 moreDon't miss the First Sunday Arts Festival! On the first Sunday of the month, West Street and Calvert Street are closed for a family friendly festival. It has over 150 …
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Spring Fest
Annapolis SDA Church 1996 Generals Highway, Annapolis, United StatesSpringfest – Family Fun Event! 🌸🎉 Join us for a FREE, family-friendly Springfest filled with fun for everyone! Enjoy face painting, a bouncy house, games, prizes, and more. There will …
Free