Activities
Events
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AACS Middle School Visit Days
Annapolis Area Christian School 109 Burns Crossing Rd, Severn, United StatesJoin us for our Middle School Visit Days on October 15 and November 19 and experience the AACS difference! Register here! (DNML)
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Annapolis Sailboat Show
Annapolis City Dock One Dock Street, Annapolis, MD, United StatesSailors from around the globe gather in beautiful downtown Annapolis every October for the Annapolis Sailboat Show. This annual celebration of sailing features floating docks lined with sailboats from manufacturers …
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Fall Girls’ Night at Grow: Pumpkin Painting
Ridge Grow 244 Old Mill Bottom Rd S, Annapolis, United StatesGrab a friend and join us for a cozy fall evening at Ridge Grow! Thursday, October 15 | 5:30–7:00 PM $25 per person | Only 15 spots Paint your own …
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Business Hall of Fame Awards Dinner
DoubleTree Hotel 210 Holiday Ct, Annapolis, United StatesPlease join the Chamber in the celebration of this year's 2026 Business Hall of Fame inductees. This event will take place at DoubleTree Annapolis. (DNML)
$150 – $175 -
Locally Gathered HERE. a pop-up shop
Locally Gathered HERE. a pop-up shop 110 Dock Street, Annapolis, United StatesDon't miss Locally Gathered HERE. a pop-up shop! It will be open from October 16 to November 8, 2026. There will be so many amazing makers and fun events! (DNML)
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B.I.G. Book Sale
Books for International Goodwill 451 Defense Hwy, Annapolis, United StatesBIG holds book sales at our warehouse, located at 451 Defense Highway, Annapolis, Maryland, eight to nine times each year. Proceeds from book sales support our shipments of books to …