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Arts & Entertainment, Community, Do Not Miss

Save The Date List

September 14, 2025 by Piper Langenfeld

Presented by

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

Thursday, October 16 | Swing Into Action | Renditions Golf Course

Thursday, October 16 – Friday, October 31 | Watermark’s and Historic Annapolis’ Special Historic Hauntings Walking Tour | 188 Main Street

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

Friday, October 17 – Sunday, November 2 | MD Corn Maze | Gambrills Road

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

Sunday, October 19 | In Gratitude: A Tribute to Earth, Wind & Fire and Sly & The Family Stone | Rams Head On Stage

Monday, October 20 | Women, Wine & Wisdom: Estate Planning | Federal House 

Tuesday, October 21 | Ignite Annapolis | Maryland Hall 

Friday, October 24 – Saturday, November 15 | Dracula: A Comedy of Terrors | Colonial Players Theater

Friday, October 24 | Pumpkin Walk | Hammond-Harwood House

Friday, October 24 | Spooky Crafts and Spirited Cocktails | Chesapeake Arts Center

Friday, October 24 | Movies Under the Stars: Moana 2 | Bay Forest Shopping Center

Friday, October 24 – Sunday, November 9 | West Side Story | Children’s Theatre of Annapolis 

Friday, October 24 | Bountiful Harvest: Costumes & Cocktails | The Atreeum at Soaring Timbers

Saturday, October 25 | Halloween Outdoor Market | Wildberry Farm 

Saturday, October 25 | Mr. Paca’s Garden Storytime: Trick or Treat on Scary Street | William Paca House & Garden

Saturday, October 25 | Navy Football vs FAU (Homecoming) | Navy-Marine Corps Memorial Stadium 

Sunday, October 26 | Anchors & Artisans | Annapolis Town Center

Monday, October 27 | Women & Investing | CovingtonAlsina: Virtual

Tuesday, October 28 | Iam Tongi | Rams Head On Stage

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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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❄️🏀 Winter Wo

❄️🏀 Winter Wonderland at Navy Basketball is back and it’s the perfect family day out! Enjoy cookie decorating, face painting, hot chocolate, holiday music, games, and so much more while cheering on Navy Men’s & Women’s Basketball in a festive doubleheader.

We love having Navy Athletics as one of our amazing Annapolis Moms community supporters, and this is such a great way to kick off the season with the kids. 🎄💙

Grab your tickets, bundle up, and make a day of it!

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Holiday Magic Awaits

Holiday Magic Awaits

This season, let Community Supporter Bayside Limousine sweep you and your loved ones into an unforgettable night of festive lights, laughter, and luxury. Relax in a chauffeur-driven limo, Sprinter, or party bus as you glide past 30+ dazzling holidays displays across the DMV — from the glowing shores of Lights on the Bay to magical park-drive-throughs. Skip traffic, parking, and stress — just cozy vibes, crisp night air, and glowing memories. Book now and make this holiday season sparkle.✨

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