Bedtime Book Buddies
Paws at the Mall 2170 Annapolis Mall Rd, Annapolis, United States
We have missed you! This October, we are delighted to host Bedtime Book Buddies nights at our brand new Paws at the Mall location. Be among the first to visit…
Events
October 2026
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Gerald Albright
Rams Head On Stage, 33 West St, Annapolis, MD 21401, USA West Street 33, Annapolis, Maryland 21401, United States
Born and raised in Los Angeles, Albright was already an accomplished saxophonist by the time he enrolled at the University of Redlands, but he switched to bass after he saw…
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You’re a Good Man, Charlie Brown – Presented by Compass Rose Theater
Live Arts Studio Westfield Mall (mall entrance by the Container store), Annapolis, MD 21401, United States
Charlie Brown – One Weekend ADDED After sold-out performances! Our Helen Hayes Recommended production of You’re A Good Man, Charlie Brown is extended through Oct. 18! Oct 15,16 & Oct…
$15 – $55
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(Extended!) You’re a Good Man, Charlie Brown – Presented by Compass Rose Theater
Live Arts Studio at Westfield Annapolis 2002 Annapolis Mall, Annapolis, 21401, United States
Charlie Brown – One Weekend ADDED After sold-out performances! Our Helen Hayes Recommended production of You’re A Good Man, Charlie Brown is extended through Oct. 18! Oct 15,16 & Oct…
$15 – $55
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AACS Middle School Visit Days
Annapolis Area Christian School 109 Burns Crossing Rd, Severn, United States
Join 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 Dock Street, Annapolis, Maryland 21401
Sailors 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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Annapolis Sailboat Show
Annapolis City Dock Dock Street, Annapolis, Maryland 21401
Walk the floating docks during the Annapolis Sailboat Show, climb aboard gleaming yachts and center consoles, and explore everything from family cruisers to weekend fishing rigs. Whether you’re boat-curious, shopping…
$10 – $32
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Let’s Get Creative! — GATHER: Learn. Connect. Thrive.
Artsy Partsy Ritchie Highway 8055, Pasadena, Maryland 21122, United States
Date: Thursday, October 15, 2026 Time: 1:00 PM – 2:00 PM Location: Artsy Partsy Studio, 8055 Ritchie Highway, Suite 302, Pasadena, MD 21122 Get creative, try something new, and discover…
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Tractor Treat 2026
Davidsonville Store 743 West Central Avenue, Davidsonville, MD 21035
Join us for a fun-filled fall evening for the whole family! Tractor Treat 2025 brings together the charm of autumn with exciting activities, delicious local eats, and plenty of treats.
$3
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Tractor Treat
Homestead Gardens – Davidsonville 743 W Central Avenue, Davidsonville, 21035, United States
Homestead Gardens is excited to welcome the community back for Tractor Treat 2026, a family-friendly fall evening celebrating local agriculture, farmers, and the equipment that keeps our community growing. Local farmers,…
$3
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Featured: Dan Haas
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Get ready for an electric night of acoustic vibes with Dan Haas at the Beer Farm! Dan’s high-energy solo set blends catchy melodies, heartfelt lyrics, and a whole lot of…
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Walk a Mile in My SHADES: White Cane Safety Day Community Celebration
Blind Industries and Services of Maryland 3345 Washington Blvd., Baltimore, Maryland 21227, United States
Join BISM and our community partners for Walk a Mile in My SHADES, a special community celebration in recognition of White Cane Safety Day! Enjoy food trucks, hands-on activities and…
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Historic Annapolis Book Club
Museum of Historic Annapolis 99 Main Street, Annapolis, 21401, United States
The Historic Annapolis Book Club invites you to explore the past through the power of storytelling. Each month, club members gather at the Museum of Historic Annapolis to discuss works of…
Free
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Cocktails 4 A Cause
Navy Marine Corps Memorial Stadium 550 Taylor Ave, Annapolis, 21401
We are excited to welcome you to Seeds 4 Success’ annual Cocktails for a Cause—an evening of purpose, progress, and possibility. Together, we’ll honor this year’s Helping Hand and Caring…
$50
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Business Hall of Fame Awards Dinner
DoubleTree Hotel 210 Holiday Ct, Annapolis, 21401, United States
Please 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
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Featured: Mahjong 102 | Guided Play – The Gardens
The Gardens 743 W Central Ave, Davidsonville, MD 21035, United States
Always wanted to learn American Mahjong? Mahjong 101 is a fun, approachable introduction for complete beginners, giving you the foundation you need to understand the game without feeling overwhelmed.
$50
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Boots & Brews at Milburn Orchards After Hours
Milburn Orchards 1495 Appleton Road, Elkton, Maryland 21921
Dust off your cowboy boots and get ready for a country night on the farm! Join us Thursday, September 17 from 6 PM–9 PM for Boots & Brews I, part…
$15
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Colonial Cocktails: Spirits with the Spirits
Historic London Town & Gardens 839 Londontown Rd, Edgewater, 21037, United States
As the sun sets and shadows grow longer, come fortify yourself with stone fence and cider syllabub as we tell ghostly stories from 18th century and learn how old world…
$34
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Featured: Garden Chores & Coffee: Plant Spring-Blooming Bulbs
Learn how to select, combine, and plant spring-blooming bulbs this fall for weeks of colorful flowers after winter.
Free
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#22FORYOU Day
Navy Marine Corps Memorial Stadium 550 Taylor Ave, Annapolis, 21401
Join Colossal on Friday, October 16, 2026, at Navy-Marine Corps Memorial Stadium in Annapolis for a meaningful day dedicated to honoring our veterans and taking action against veteran suicide. #22FORYOU…
$150
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