Best events in
Chestertown

Looking for something to do in Chestertown? Whether you're a local, new in town or just cruising through we've got loads of great tips and events. You can explore by location, what's popular, our top picks, free stuff... you got this. Ready?

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Popular in Chestertown

The Chestertown Ques & Phat Daddy’s present BBQ & Crab Feast

Tomorrow at 13:00

Minary’s Dream Alliance, Inc.

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Schooner SULTANA Public Sails 2026-August

Fri, Aug 14, 5:00 PM

Chestertown Marina

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30th & Final Chestertown Jazz Festival

Sat, Sep 12, 12:00 PM

Wilmer Park

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Bi-Monthly Bluegrass Jam

Sat, Sep 19, 1:00 PM + 10 more

Lawrence Wetlands Preserve

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Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation

Sat, Sep 19, 10:00 AM

Stillpond Creek

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Ink & Indie 2026 - Author Signing Event

Sat, Oct 3, 10:00 AM

211 High St

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2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

Fri, Oct 30, 2:30 PM

Chestertown Marina

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

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The Chestertown Ques & Phat Daddy’s present BBQ & Crab Feast

Tomorrow at 13:00

Minary’s Dream Alliance, Inc.

Check ticket price on event

Schooner SULTANA Public Sails 2026-August

Fri, Aug 14, 5:00 PM

Chestertown Marina

Check ticket price on event

30th & Final Chestertown Jazz Festival

Sat, Sep 12, 12:00 PM

Wilmer Park

Check ticket price on event

Bi-Monthly Bluegrass Jam

Sat, Sep 19, 1:00 PM + 10 more

Lawrence Wetlands Preserve

Check ticket price on event

Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation

Sat, Sep 19, 10:00 AM

Stillpond Creek

Check ticket price on event

Ink & Indie 2026 - Author Signing Event

Sat, Oct 3, 10:00 AM

211 High St

Check ticket price on event

2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

Fri, Oct 30, 2:30 PM

Chestertown Marina

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

Check ticket price on event

Online Events

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Stockage PV de A à Z : maîtrisez les bases pour vos projets

Tomorrow at 09:30 GMT+2

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Financer votre entreprise grâce à Futurpreneur

Tuesday at 11:00 EDT

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Boston Career Fair

Thu, Aug 6, 9:30 AM EDT

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Despo party

Sat, Aug 8, 2:00 PM GMT+2

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Pie & AI: Repetitive task to Autonomous Agent: Automating an end-to-end business process with agentic AI

Wed, Aug 12, 1:30 PM UTC

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NASA's Nancy Grace Roman Space Telescope Launch

Sun, Aug 30, 7:20 AM EDT

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Webinaire Réformes RSE marchés publics : êtes-vous prêts ?

Tue, Sep 1, 2:00 PM GMT+2

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MASTERCLASS Peindre un Oiseau • Séance I

Tue, Sep 1, 8:00 AM AST

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Stockage PV de A à Z : maîtrisez les bases pour vos projets

Tomorrow at 09:30 GMT+2

Check ticket price on event

Financer votre entreprise grâce à Futurpreneur

Tuesday at 11:00 EDT

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Boston Career Fair

Thu, Aug 6, 9:30 AM EDT

Check ticket price on event

Despo party

Sat, Aug 8, 2:00 PM GMT+2

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Pie & AI: Repetitive task to Autonomous Agent: Automating an end-to-end business process with agentic AI

Wed, Aug 12, 1:30 PM UTC

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NASA's Nancy Grace Roman Space Telescope Launch

Sun, Aug 30, 7:20 AM EDT

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Webinaire Réformes RSE marchés publics : êtes-vous prêts ?

Tue, Sep 1, 2:00 PM GMT+2

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MASTERCLASS Peindre un Oiseau • Séance I

Tue, Sep 1, 8:00 AM AST

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From nearby cities

The 15th Annual New York City Poetry Festival

Tomorrow at 11:00

Nolan Park

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BLUNTS & BRUNCH: BROOKLYN, NY ( PLEASE WEAR WHITE☮️)

Tomorrow at 13:00

740 5th Ave

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ROSA: A National Tequila Day Celebration

Sun, Jul 26, 3:00 PM

Dirty Habit

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MahoganyBooks Presents Black Books Matter Fest 2026

Sat, Aug 1, 11:00 AM

MahoganyBooks - National Harbor

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USA REVIVAL FIRE CRUSADE

Thu, Aug 13, 5:30 PM

Prince George's Stadium

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Philadelphia Taco Festival

Sat, Aug 15, 2:00 PM

Stateside Live!

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Indies & Bookworms Signing Event

Sat, Aug 15, 11:00 AM

Rita Rossi Colwell Center

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Albany Career Fair

Wed, Aug 19, 9:30 AM

Hyatt

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The 15th Annual New York City Poetry Festival

Tomorrow at 11:00

Nolan Park

Check ticket price on event

BLUNTS & BRUNCH: BROOKLYN, NY ( PLEASE WEAR WHITE☮️)

Tomorrow at 13:00

740 5th Ave

Check ticket price on event

ROSA: A National Tequila Day Celebration

Sun, Jul 26, 3:00 PM

Dirty Habit

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MahoganyBooks Presents Black Books Matter Fest 2026

Sat, Aug 1, 11:00 AM

MahoganyBooks - National Harbor

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USA REVIVAL FIRE CRUSADE

Thu, Aug 13, 5:30 PM

Prince George's Stadium

Check ticket price on event

Philadelphia Taco Festival

Sat, Aug 15, 2:00 PM

Stateside Live!

Check ticket price on event

Indies & Bookworms Signing Event

Sat, Aug 15, 11:00 AM

Rita Rossi Colwell Center

Check ticket price on event

Albany Career Fair

Wed, Aug 19, 9:30 AM

Hyatt

Check ticket price on event

Points of Interest near Chestertown

Massoniart Gallery