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Chestertown
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Most popular events

Town Square Fall 2025 Vendor Fair primary image

Town Square Fall 2025 Vendor Fair

Sat, Nov 8, 10:00 AM

9708 Belair Rd

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The Party of the Year: GATSBY primary image

The Party of the Year: GATSBY

Fri, Nov 21, 8:30 PM

Chesapeake Inn Restaurant & Marina

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Bonfire & Harvest Night primary image

Bonfire & Harvest Night

Sun, Nov 9, 3:30 PM

Huck and Buck Farm, LLC

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Autumn Harvest Brunch in Annapolis primary image

Autumn Harvest Brunch in Annapolis

Sun, Nov 23, 11:30 AM

172 Green St

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TRFQ Cuffin Szn Social primary image

TRFQ Cuffin Szn Social

Sat, Nov 22, 8:45 PM

Baltimore Unity Hall

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Crafts, Cider & Candy Harvest Family Fun primary image

Crafts, Cider & Candy Harvest Family Fun

Friday at 17:00

The CURE (Division St. Location)

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CTR Fall Festival primary image

CTR Fall Festival

Thursday at 17:00 + 3 more

1136 Priestford Rd

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Pumpkin Fall Floral Centerpiece primary image

Pumpkin Fall Floral Centerpiece

Sun, Nov 16, 2:00 PM

Rising Sun Inn, Historic Tavern and Museum`

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