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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
Where to Catch Live Music in Annapolis