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Historic events
in Chestertown, MD

Historic
Chestertown
Date
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2026 Wedding Fair at the Historic Inns of Annapolis primary image

2026 Wedding Fair at the Historic Inns of Annapolis

Sun, Mar 22 • 12:00 PM

The Governor Calvert House at Historic Inns of Annapolis

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Eccentryk Lady Ryderz SC 2ND Annual MLK/BLK History Month Celebration

Sat, Mar 7 • 4:00 PM

Cedar Morris Hill Park

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February 2026 Taste & Tour primary image

February 2026 Taste & Tour

Wed, Feb 18 • 6:00 PM

Garrett Jacobs Mansion

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Walking Tour: Lost History of Frederick (Bailey) Douglass in Old Annapolis primary image

Walking Tour: Lost History of Frederick (Bailey) Douglass in Old Annapolis

Fri, Apr 3 • 10:30 AM

Kunta Kinte-Alex Haley Memorial

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Wars of the Roses Con primary image

Wars of the Roses Con

Sat, Feb 14 • 5:00 PM

Maritime Conference Center

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Visit the Quaint Town of St. Michaels & Enjoy a Winery Tasting Tour primary image

Visit the Quaint Town of St. Michaels & Enjoy a Winery Tasting Tour

Thu, May 7 • 9:00 AM

St. Michaels Maryland

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Fireside Evening with Harriet Tubman primary image

Fireside Evening with Harriet Tubman

Sun, Mar 1 • 6:00 PM

Linville Manor (Bowie-Johnson House)

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Jazz Brunch and Black History Celebration primary image

Jazz Brunch and Black History Celebration

Saturday • 10:00 AM

14300 St Thomas Church Rd

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