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Discover fall magic at these events in Kent County

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With fall in full swing at the Eastern Shore, Kent County invites visitors and residents to celebrate the season with a vibrant lineup of autumn events.

From traditional harvest festivals to exciting waterfront gatherings, there is something for everyone to enjoy this October.

FallFest in Rock Hall

Kick off the seasonal festivities at FallFest in Rock Hall, a beloved community tradition celebrating country music, local oysters and artisanal crafts. Families can enjoy live entertainment, taste delicious cuisine from the Bay and find plenty of kids' activities along the scenic waterfront.

Witches Weekend in Rock Hall

Embrace the spooky side of autumn with Witches Weekend in Rock Hall. Townsfolk and guests alike don their best witchy attire for a playful weekend featuring merchant specials, costume contests and festive gatherings across local shops and eateries.

Downrigging Weekend in Chestertown

Round out your autumn adventures at Downrigging Weekend in Chestertown, one of the largest annual tall ship maritime festivals on the East Coast. Experience wooden boat displays, public sails, world-class music and lectures celebrating maritime heritage along the Chester River.

Plan your trip today and experience autumn at its best in Kent County!


Kent County Tourism is part of The Guide Community Connect sponsored content program.

Kent County events, FallFest Rock Hall, Witches Weekend, Downrigging Weekend Chestertown, Maryland autumn festivals, Eastern Shore fall activities

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