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Events and Things to do in Chestertown, MD

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Almost full
Bimbo Bingo - Market Street Brewery
Saturday at 6:30 PM
Havre de Grace · Market Street Brewery
Almost full
Bimbo Bingo - Market Street Brewery
Saturday at 6:30 PM
Havre de Grace · Market Street Brewery
Real Estate Rumble 2026-After Party Celebration!
Wed, Jun 3, 2:00 PM
Stevensville · The Edge Arena
Real Estate Rumble 2026-After Party Celebration!
Wed, Jun 3, 2:00 PM
Stevensville · The Edge Arena
Independence Day Kickoff
Thu, May 28, 5:30 PM
Havre de Grace · Vandiver Inn
Independence Day Kickoff
Thu, May 28, 5:30 PM
Havre de Grace · Vandiver Inn
9th Annual Arts, Wine, Jazz & Soul Festival
Sat, Aug 8, 12:00 PM
Havre de Grace · Concord Point Lighthouse Keeper's House
9th Annual Arts, Wine, Jazz & Soul Festival
Sat, Aug 8, 12:00 PM
Havre de Grace · Concord Point Lighthouse Keeper's House
Sales end soon
Family Game Night at sweetFrog Kent Island
Tomorrow at 5:00 PM + 7 more
Chester · sweetFrog Kent Island
Sales end soon
Family Game Night at sweetFrog Kent Island
Tomorrow at 5:00 PM + 7 more
Chester · sweetFrog Kent Island
Going fast
The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH
Sun, Jun 28, 2:00 PM
Havre de Grace · The STAR Centre
Going fast
The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH
Sun, Jun 28, 2:00 PM
Havre de Grace · The STAR Centre
Going fast
The Bacon Brothers
Sat, Jul 18, 8:00 PM
Havre de Grace · The STAR Centre
Going fast
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
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
Goat Yoga at Pooles Island Brewing Co.
Sat, Jun 20, 11:00 AM
Middle River · Pooles Island Brewing Company
Goat Yoga at Pooles Island Brewing Co.
Sat, Jun 20, 11:00 AM
Middle River · Pooles Island Brewing Company
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
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
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
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
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
Almost full
STAR Summer Camp: Tumbling Camp (Grades 2-6)
Havre de Grace · The STAR Centre
Almost full
STAR Summer Camp: Tumbling Camp (Grades 2-6)
Havre de Grace · The STAR Centre
Harmony Woods Music & Arts Fest
Fri, Jun 19, 5:00 PM
Bel Air · 2503 S Tollgate Rd
Harmony Woods Music & Arts Fest
Fri, Jun 19, 5:00 PM
Bel Air · 2503 S Tollgate Rd
Almost full
STAR Summer Camp: STAR Artists Camp
Havre de Grace · The STAR Centre
Almost full
STAR Summer Camp: STAR Artists Camp
Havre de Grace · The STAR Centre
Sales end soon
Qigong Class
Sunday at 11:00 AM + 63 more
Edgewood · 2120 Emmorton Park Rd
Sales end soon
Qigong Class
Sunday at 11:00 AM + 63 more
Edgewood · 2120 Emmorton Park Rd
6th Annual Susquehanna Wine & Seafood Fest
Sat, Sep 19, 12:00 PM
Havre de Grace · 701 Concord St
6th Annual Susquehanna Wine & Seafood Fest
Sat, Sep 19, 12:00 PM
Havre de Grace · 701 Concord St

Trends in Chestertown

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Explore more trends

Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

Real Estate Rumble 2026-After Party Celebration!

9th Annual Arts, Wine, Jazz & Soul Festival

The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH

The Bacon Brothers

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

events happening today near me

mothers day brunch ballys

Which events are coming up?

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

Family Game Night at sweetFrog Kent Island

Bimbo Bingo - Market Street Brewery

Independence Day Kickoff