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Events and Things to do in Chestertown, MD

Search for something you love or check out popular events in your area.

Mojo Car Show 2026
Sun, Aug 2, 12:00 PM
Edgewood · Cunion Field
Mojo Car Show 2026
Sun, Aug 2, 12:00 PM
Edgewood · Cunion Field
Sales end soon
PRIDE MONTH Drag Ball! Drag Me to the Royal Hosted by Sorority Heights
Tomorrow at 8:00 PM
Edgewood · The Royal Palace Ballroom
Sales end soon
PRIDE MONTH Drag Ball! Drag Me to the Royal Hosted by Sorority Heights
Tomorrow at 8:00 PM
Edgewood · The Royal Palace Ballroom
Ink & Indie 2026 - Author Signing Event
Sat, Oct 3, 10:00 AM
Chestertown · 211 High St
Ink & Indie 2026 - Author Signing Event
Sat, Oct 3, 10:00 AM
Chestertown · 211 High St
Saber The Moment World Record and Summer Concert - Separate Ways The Band
Sat, Jul 18, 4:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Saber The Moment World Record and Summer Concert - Separate Ways The Band
Sat, Jul 18, 4:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Oliver Beach Inn Paint Night
Thu, Jul 9, 6:00 PM
Middle River · Oliver Beach Inn
Oliver Beach Inn Paint Night
Thu, Jul 9, 6:00 PM
Middle River · Oliver Beach Inn
Sales end soon
Kings Dominion Bus Trip
Tue, Jul 21, 8:30 AM
Grasonville · Grasonville Community Center
Sales end soon
Kings Dominion Bus Trip
Tue, Jul 21, 8:30 AM
Grasonville · Grasonville Community Center
Almost full
Maryland Crop Scouting School at WYE
Thu, Jun 25, 9:00 AM
Queenstown · Wye Research & Education Center
Almost full
Maryland Crop Scouting School at WYE
Thu, Jun 25, 9:00 AM
Queenstown · Wye Research & Education Center
Federated Wrestling Alliance: Prestige
Sun, Jun 28, 4:00 PM
Edgewood · The Royal Palace Ballroom
Federated Wrestling Alliance: Prestige
Sun, Jun 28, 4:00 PM
Edgewood · The Royal Palace Ballroom
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
The Towson - Catonsville Alumni Kappa Bash Over the Bridge
Sat, Aug 29, 9:00 AM
Grasonville · Fisherman's Crab Deck
The Towson - Catonsville Alumni Kappa Bash Over the Bridge
Sat, Aug 29, 9:00 AM
Grasonville · Fisherman's Crab Deck
4th of July Fireworks Show on the Boh
Sat, Jul 4, 7:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
4th of July Fireworks Show on the Boh
Sat, Jul 4, 7:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Sales end soon
Beginner Yoga Every Tuesday & Thursday
Today at 6:00 PM + 28 more
Edgewood · 2120 Emmorton Park Rd
Sales end soon
Beginner Yoga Every Tuesday & Thursday
Today at 6:00 PM + 28 more
Edgewood · 2120 Emmorton Park Rd
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
The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH
Sun, Jun 28, 2:00 PM
Havre de Grace · The STAR Centre
Almost full
The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH
Sun, Jun 28, 2:00 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
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
Predicamos: Palabra viva, una voz en misión
Fri, Aug 21, 7:00 PM
Edgemere · 7517 North Point Rd
Predicamos: Palabra viva, una voz en misión
Fri, Aug 21, 7:00 PM
Edgemere · 7517 North Point Rd
Sales end soon
Sunset Floating Sound Bath with Artist Katie Detrich
Saturday at 6:45 PM
Pasadena · Cedarwood Cove Pool Association
Sales end soon
Sunset Floating Sound Bath with Artist Katie Detrich
Saturday at 6:45 PM
Pasadena · Cedarwood Cove Pool Association
Sales end soon
Fathers Day Crabs on the Bay
Sunday at 11:30 AM
Essex · Maryland Party Boat Charters
Sales end soon
Fathers Day Crabs on the Bay
Sunday at 11:30 AM
Essex · Maryland Party Boat Charters
Hat & Bag Burn Workshop at Moonlight Collective Studios
Fri, Jun 26, 6:00 PM
Abingdon · Moonlight Collective Studios
Hat & Bag Burn Workshop at Moonlight Collective Studios
Fri, Jun 26, 6:00 PM
Abingdon · Moonlight Collective Studios

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:

Mojo Car Show 2026

Ink & Indie 2026 - Author Signing Event

Saber The Moment World Record and Summer Concert - Separate Ways The Band

Oliver Beach Inn Paint Night

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:

Beginner Yoga Every Tuesday & Thursday

PRIDE MONTH Drag Ball! Drag Me to the Royal Hosted by Sorority Heights

Sunset Floating Sound Bath with Artist Katie Detrich

Fathers Day Crabs on the Bay