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Events and Things to do in Chestertown, MD

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Bethlehem Church Paint Day
Sat, Jun 27, 11:00 AM
Baltimore · Bethlehem Church
Bethlehem Church Paint Day
Sat, Jun 27, 11:00 AM
Baltimore · Bethlehem Church
Almost full
The Bacon Brothers
Sat, Jul 18, 8:00 PM
Havre de Grace · The STAR Centre
Almost full
The Bacon Brothers
Sat, Jul 18, 8:00 PM
Havre de Grace · The STAR Centre
1st Annual Rep Your Colors Party
Sun, Jun 28, 3:00 PM
Essex · 1909 Old Eastern Ave
1st Annual Rep Your Colors Party
Sun, Jun 28, 3:00 PM
Essex · 1909 Old Eastern Ave
Short Attention Span Theatre 2026 at the Garfield Center
Fri, Jun 19, 8:00 PM + 8 more
Chestertown · Garfield Center for the Arts at the Prince Theatre
Short Attention Span Theatre 2026 at the Garfield Center
Fri, Jun 19, 8:00 PM + 8 more
Chestertown · Garfield Center for the Arts at the Prince Theatre
Charly's Waterfront Paint Night
Wed, Jun 17, 6:00 PM
Essex · Charly's Waterfront
Charly's Waterfront Paint Night
Wed, Jun 17, 6:00 PM
Essex · Charly's Waterfront
Classic Reels and Good Feels...A Summer Movie Night
Wed, Jun 17, 6:00 PM
Stevensville · Kent Island Resort
Classic Reels and Good Feels...A Summer Movie Night
Wed, Jun 17, 6:00 PM
Stevensville · Kent Island Resort
Mat O'Neill Presents: UNFORGETTABLE
Sat, Jun 6, 7:00 PM
Havre de Grace · Cultural Center at the Opera House
Mat O'Neill Presents: UNFORGETTABLE
Sat, Jun 6, 7:00 PM
Havre de Grace · Cultural Center at the Opera House
Almost full
PCBT's Summer Concert: Saturday, June 13th
Sat, Jun 13, 2:00 PM
Clayton · Providence Creek Ballet Theater
Almost full
PCBT's Summer Concert: Saturday, June 13th
Sat, Jun 13, 2:00 PM
Clayton · Providence Creek Ballet Theater
Family Game Night at sweetFrog Kent Island
Thu, Jun 18, 5:00 PM + 6 more
Chester · sweetFrog Kent Island
Family Game Night at sweetFrog Kent Island
Thu, Jun 18, 5:00 PM + 6 more
Chester · sweetFrog Kent Island
Going fast
10th Anniversary Celebration" presented by Bel Air Dance Academy
Sat, Jun 13, 12:00 PM
Havre de Grace · Cultural Center at the Opera House
Going fast
10th Anniversary Celebration" presented by Bel Air Dance Academy
Sat, Jun 13, 12:00 PM
Havre de Grace · Cultural Center at the Opera House
Almost full
PCBT's Summer Concert: Sunday, June 14th
Sun, Jun 14, 2:00 PM
Clayton · Providence Creek Ballet Theater
Almost full
PCBT's Summer Concert: Sunday, June 14th
Sun, Jun 14, 2:00 PM
Clayton · Providence Creek Ballet Theater
The STAR Centre Presents: Dirty Deeds
Sat, Jun 27, 8:00 PM
Havre de Grace · The STAR Centre
The STAR Centre Presents: Dirty Deeds
Sat, Jun 27, 8:00 PM
Havre de Grace · The STAR Centre
Almost full
Expansion: Creating Space for New Possibilities — Gazespotting, Meditation
Sun, Jun 28, 10:00 AM
Pasadena · Dun-Pikin Farm
Almost full
Expansion: Creating Space for New Possibilities — Gazespotting, Meditation
Sun, Jun 28, 10:00 AM
Pasadena · Dun-Pikin Farm
Almost full
2026 Fall Craft Fair
Sat, Nov 14, 10:00 AM
Pasadena · Chesapeake High School
Almost full
2026 Fall Craft Fair
Sat, Nov 14, 10:00 AM
Pasadena · Chesapeake High School
Going fast
Teen Musical Theatre Camp: DEAR EVAN HANSEN (Grades Rising 9-12)
Mon, Jun 29, 9:00 AM
Havre de Grace · The STAR Centre
Going fast
Teen Musical Theatre Camp: DEAR EVAN HANSEN (Grades Rising 9-12)
Mon, Jun 29, 9:00 AM
Havre de Grace · The STAR Centre
BodyJam & Hip-Hop Abs Fusion for Pride
Fri, Jun 12, 6:00 PM
Nottingham · Merritt Clubs White Marsh
BodyJam & Hip-Hop Abs Fusion for Pride
Fri, Jun 12, 6:00 PM
Nottingham · Merritt Clubs White Marsh
Almost full
A Taste of Maryland: A Sweet Wine Tasting
Wed, Jun 17, 6:00 PM
Dundalk · Drug City Tasting Room
Almost full
A Taste of Maryland: A Sweet Wine Tasting
Wed, Jun 17, 6:00 PM
Dundalk · Drug City Tasting Room
Middle River Fire Works Cruise
Sat, Jul 4, 7:00 PM
Essex · Maryland Party Boat Charters
Middle River Fire Works Cruise
Sat, Jul 4, 7:00 PM
Essex · Maryland Party Boat Charters
Sunset Floating Sound Bath with Artist Katie Detrich
Sat, Jun 20, 6:45 PM
Pasadena · Cedarwood Cove Pool Association
Sunset Floating Sound Bath with Artist Katie Detrich
Sat, Jun 20, 6:45 PM
Pasadena · Cedarwood Cove Pool Association
Kings Dominion Bus Trip
Tue, Jul 21, 8:30 AM
Grasonville · Grasonville Community Center
Kings Dominion Bus Trip
Tue, Jul 21, 8:30 AM
Grasonville · Grasonville Community Center

Trends in Chestertown

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Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

Bethlehem Church Paint Day

The Bacon Brothers

1st Annual Rep Your Colors Party

Short Attention Span Theatre 2026 at the Garfield Center

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

events happening today near me

yard sales and estate sale

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Mat O'Neill Presents: UNFORGETTABLE

BodyJam & Hip-Hop Abs Fusion for Pride

10th Anniversary Celebration" presented by Bel Air Dance Academy

PCBT's Summer Concert: Saturday, June 13th