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

Short Attention Span Theatre 2026 at the Garfield Center

Thursday at 20:00 + 2 more

Garfield Center for the Arts at the Prince Theatre

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

Sun, Jul 19, 1:00 PM

Minary’s Dream Alliance, Inc.

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Schooner SULTANA Public Sails 2026-July

Fri, Jul 24, 5:00 PM

Chestertown Marina

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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 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

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2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm

Sat, Oct 31, 2:30 PM

Chestertown Marina

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Short Attention Span Theatre 2026 at the Garfield Center

Thursday at 20:00 + 2 more

Garfield Center for the Arts at the Prince Theatre

Check ticket price on event

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

Sun, Jul 19, 1:00 PM

Minary’s Dream Alliance, Inc.

Check ticket price on event

Schooner SULTANA Public Sails 2026-July

Fri, Jul 24, 5:00 PM

Chestertown Marina

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

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Ink & Indie 2026 - Author Signing Event

Sat, Oct 3, 10:00 AM

211 High St

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

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2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm

Sat, Oct 31, 2:30 PM

Chestertown Marina

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Online Events

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How to Build a Side Hustle with AI in One Weekend

Today at 19:00 PDT

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MoneyOwl Webinar: Retirement Income Dilemmas

Thursday at 19:30 GMT+8

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How to Do a Venture Capital Financing!

Thu, Jul 9, 9:00 AM PDT

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Human Rights, Sustainable Development & the Law

Fri, Jul 10, 8:30 AM EDT

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Sorted Live: Back To Their Old School

Sat, Jul 25, 12:00 PM GMT+1

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San Diego Career Fair

Mon, Jul 27, 9:30 AM PDT

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Las Vegas Hiring Event

Fri, Aug 21, 9:30 AM PDT

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NASA's Nancy Grace Roman Space Telescope Launch

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How to Build a Side Hustle with AI in One Weekend

Today at 19:00 PDT

Check ticket price on event

MoneyOwl Webinar: Retirement Income Dilemmas

Thursday at 19:30 GMT+8

Check ticket price on event

How to Do a Venture Capital Financing!

Thu, Jul 9, 9:00 AM PDT

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Human Rights, Sustainable Development & the Law

Fri, Jul 10, 8:30 AM EDT

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Sorted Live: Back To Their Old School

Sat, Jul 25, 12:00 PM GMT+1

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San Diego Career Fair

Mon, Jul 27, 9:30 AM PDT

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Las Vegas Hiring Event

Fri, Aug 21, 9:30 AM PDT

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NASA's Nancy Grace Roman Space Telescope Launch

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From nearby cities

NEW DATE - Culture Fest 2026

Sunday at 15:00

Liberty Point

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Afrobeats & Wine Festival '26 - DC

Sunday at 14:00

Union Market

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2026 New Jersey Jeep Invasion - Wildwood, NJ

Fri, Jul 10, 9:00 AM

4501 Boardwalk

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The 15th Annual New York City Poetry Festival

Sat, Jul 18, 11:00 AM

Nolan Park

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MIDNIGHT RUN PHILLY

Sat, Jul 25, 10:00 PM

Meet in Parking Lot

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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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New Jersey African Restaurant Week Festival 2026

Sat, Aug 22, 12:00 PM

Source of Knowledge (Street Festival)

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NEW DATE - Culture Fest 2026

Sunday at 15:00

Liberty Point

Check ticket price on event

Afrobeats & Wine Festival '26 - DC

Sunday at 14:00

Union Market

Check ticket price on event

2026 New Jersey Jeep Invasion - Wildwood, NJ

Fri, Jul 10, 9:00 AM

4501 Boardwalk

Check ticket price on event

The 15th Annual New York City Poetry Festival

Sat, Jul 18, 11:00 AM

Nolan Park

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MIDNIGHT RUN PHILLY

Sat, Jul 25, 10:00 PM

Meet in Parking Lot

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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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New Jersey African Restaurant Week Festival 2026

Sat, Aug 22, 12:00 PM

Source of Knowledge (Street Festival)

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Points of Interest near Chestertown

Massoniart Gallery