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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

September 9, 2025 by Piper Langenfeld

Week of 9/11-9/17

Presented by

Thursday, September 11 – Sunday, September 14 | Anne Arundel County Fair | Anne Arundel County Fairgrounds 

Thursday, September 11 – Sunday, September 14 | Annapolis Songwriters Festival | Annapolis

Thursday, September 11 | Black & White Gala | The Atreeum at Soaring Timbers 

Friday, September 12 | Small Business Owner/Entrepreneur Support Group | Betty Center

Friday, September 12 | Dirty Heads with BALLYHOO! & Wheeland Brothers | Calvert Street Stage

Saturday, September 13 | Second Saturday Divorce Workshop | CovingtonAlsina: Virtual

Saturday, September 13 | An Introduction To Your Human Design | Annapolis Crystals 

Saturday, September 13 | Watermark’s Weird, Wacky, & Unusual History of Annapolis Tour | 188 Main Street

Saturday, September 13 | Naptown Pop Up Market | Annapolis Town Center

Saturday, September 13 | Kunta Kinte Heritage Festival | Navy-Marine Corps Memorial Stadium

Saturday, September 13 & Sunday, September 14 | MD Corn Maze | Gambrills Road 

Saturday, September 13 | Tunes Through Time: The Sounds of Early Annapolis | Hogshead Trades Museum

Saturday, September 13 | Hunger Action Month Food Drive Event | Himmel’s Landscape and Garden Center

Saturday, September 13 & Sunday, September 14 | Maryland Seafood Festival | Sandy Point State Park

Saturday, September 13 | Live Music from Alex Peters | O’Loughlin’s Restaurant

Saturday, September 13 | Watermark’s Songwriters on the Severn | Annapolis City Dock

Sunday, September 14 | Annapolis RUN for The Light House | Quiet Waters Park  

Sunday, September 14 | Mrs. Howard’s Coffee House | Hogshead Trades Museum

Sunday, September 14 | Annapolis Vintage Market | Vintage Vibe Finds

Monday, September 15 & Tuesday, September 16 | 1920s Cabaret: The Speakeasy | Classic Theatre of Maryland 

Monday, September 15 | Casey Abrams & Friends featuring Dylan Chambers and Hunter | Rams Head On Stage

Tuesday, September 16 | Women, Wine & Wisdom: Aging in Place | Federal House 

Wednesday, September 17 | FarmUnity Harvest Festival | Crofton Library

Wednesday, September 17 | The Constitution: Promises and Challenges | Historic Annapolis: Virtual

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Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

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Join the Chesapeake Baysox on Sunday, June 21 for our Father's Day BBQ featuring a two-hour all-you-can-eat buffet with flank steak, Old Bay roasted chicken, a sausage bar, mac & cheese, desserts, and more before Baysox baseball at 1:05 PM.

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