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Arts & Entertainment, Community, Do Not Miss

Save The Date List

September 7, 2025 by Piper Langenfeld

Presented by

Wednesday, October 8 – Friday, October 31 | Watermark’s & Historic Annapolis’ Special Historic Hauntings Walking Tour | 188 Main Street

Wednesday, October 8 | The Garden Ramble with the Black-Eyed Suzies | Historic London Town & Gardens

Wednesday, October 8 – Sunday, November 2 | MD Corn Maze | Gambrills Road

Thursday, October 9 – Sunday, October 12 | Annapolis Sailboat Show | Annapolis City Dock

Friday, October 10 & Saturday, October 11 | A New World | Maryland Hall 

Saturday, October 11 & Sunday, October 12 | Art @ the Park | Quiet Waters Park

Saturday, October 11 | Bird Watching 101: Heading South for the Winter | Historic London Town & Gardens

Saturday, October 11 | Party in the ‘Port | Eastport Yacht Club

Saturday, October 11 & Sunday, October 12 | Audition for Holes | Children’s Theatre of Annapolis 

Saturday, October 11 | Close Enemies featuring Tom Hamilton of Aerosmith | Rams Head On Stage

Saturday, October 11 | Second Saturday Divorce Workshop | CovingtonAlsina: Virtual

Sunday, October 12 | A Conversation with Abby Phillip | Maryland Hall 

Sunday, October 12 | Nutcracker Storytime | William Paca House & Garden 

Sunday, October 12 | Wildflowers | Maryland Hall

Monday, October 13 | Columbus Day Brunch | Urbano 

Monday, October 13 | Social Security Webinar | CovingtonAlsina: Virtual

Tuesday, October 14 | Birds of a Feather | Historic London Town & Gardens

Tuesday, October 14 | National Dessert Day | Federal House 

Tuesday, October 14 | Northern Slavery in Colonial America | Historic Annapolis: Virtual

Thursday, October 16 | Colonial Cocktails: Spirits with the Spirits | Historic London Town & Gardens

Friday, October 17 – Sunday, October 19 | Ballet Theatre of Maryland’s Giselle | Maryland Hall

Friday, October 17 | Women in Business Networking Event | Trendy Tides Boutique

Saturday, October 18 | Defenders of the Chesapeake: Maryland State Marines | Hogshead Trades Museum 

Saturday, October 18 & Sunday, October 19 | The Wine Festival | Kurtz’s Beach

Saturday, October 18 | Bull & Oyster Roast | The Gunston School 
Sunday, October 19 | Watermark’s Fall Foliage Bay Lighthouse Cruise | Annapolis City Dock

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

About Piper Langenfeld

Previous Post:Graphic of lighthouse and bridge with "Annapolis Songwriters Festival" written on it.Know Before You Go: Annapolis Songwriters Festival
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Treat Mom (or yourself ) to something she’d never book on her own with the ProMD Health Annapolis Mother’s Day Beauty Bundle!

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🎨✨ Mandala Pain

🎨✨ Mandala Paint Night is calling! ✨🎨

Looking for a fun, relaxing night out? Join our Community Supporter Julep Kitchen & Bar on Thursday, May 7 for an evening of creativity, connection, and good vibes 💫

No art experience needed, just bring yourself (and maybe a friend or two!). You’ll be guided through creating your own beautiful mandala while enjoying:

🍽️ A small plates menu item
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Come solo or with your crew either way, you’ll leave inspired (and with your own masterpiece!).

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