Events and Things to do in Chestertown, MD

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PT. 2 ON THE WATER
Sun, Jun 14, 4:00 PM
Pasadena · Kurtz's Beach Ltd
PT. 2 ON THE WATER
Sun, Jun 14, 4:00 PM
Pasadena · Kurtz's Beach Ltd
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
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
CrankNCruise Ft. New Impressionz
Sun, Jun 14, 4:30 PM
Essex · 1901 Old Eastern Ave
CrankNCruise Ft. New Impressionz
Sun, Jun 14, 4:30 PM
Essex · 1901 Old Eastern Ave
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
Needle Felting on the Bohemia - Painting with wool
Wed, Jun 10, 6:30 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Needle Felting on the Bohemia - Painting with wool
Wed, Jun 10, 6:30 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Almost full
Rage Box presents: Re: DEFINITION
Sun, Jun 14, 1:00 PM
Havre de Grace · The STAR Centre
Almost full
Rage Box presents: Re: DEFINITION
Sun, Jun 14, 1:00 PM
Havre de Grace · The STAR Centre
Bohemia live! Summer Concert Series - Separate Ways The Band
Sat, Jul 18, 7:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Bohemia live! Summer Concert Series - Separate Ways The Band
Sat, Jul 18, 7:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Almost full
Rage Box presents: "Let's Go To The Movies!"
Sat, Jun 13, 11:00 AM
Havre de Grace · The STAR Centre
Almost full
Rage Box presents: "Let's Go To The Movies!"
Sat, Jun 13, 11:00 AM
Havre de Grace · The STAR Centre
Going fast
Fashion in Motion: From City to Runway Brunch & Fashion Show
Sat, Jun 13, 1:00 PM
White Marsh · 11135 Pulaski Hwy
Going fast
Fashion in Motion: From City to Runway Brunch & Fashion Show
Sat, Jun 13, 1:00 PM
White Marsh · 11135 Pulaski Hwy
Almost full
Rage Box presents: Re: DEFINITION - Division 1, 7-18 yr. olds
Sat, Jun 13, 7:00 PM
Havre de Grace · The STAR Centre
Almost full
Rage Box presents: Re: DEFINITION - Division 1, 7-18 yr. olds
Sat, Jun 13, 7:00 PM
Havre de Grace · The STAR Centre
Sales end soon
Beginner Yoga Every Tuesday & Thursday
Thursday at 6:00 PM + 30 more
Edgewood · 2120 Emmorton Park Rd
Sales end soon
Beginner Yoga Every Tuesday & Thursday
Thursday at 6:00 PM + 30 more
Edgewood · 2120 Emmorton Park Rd
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
SINATRA AT THE SANDS with Chris Pinnella
Sun, Jun 7, 3:00 PM
Havre de Grace · The STAR Centre
SINATRA AT THE SANDS with Chris Pinnella
Sun, Jun 7, 3:00 PM
Havre de Grace · The STAR Centre
Sales end soon
Dance Conservatory of Maryland presents: June Concert
Saturday at 11:00 AM
Havre de Grace · The STAR Centre
Sales end soon
Dance Conservatory of Maryland presents: June Concert
Saturday at 11:00 AM
Havre de Grace · The STAR Centre
Going fast
Maryland Crop Scouting School at WYE
Thu, Jun 25, 9:00 AM
Queenstown · Wye Research & Education Center
Going fast
Maryland Crop Scouting School at WYE
Thu, Jun 25, 9:00 AM
Queenstown · Wye Research & Education Center
Sales end soon
Elegant Afternoon Tea at Brampton 1860
Sunday at 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
Sales end soon
Elegant Afternoon Tea at Brampton 1860
Sunday at 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
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
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
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

Trends in Chestertown

Explore more trends

Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

PT. 2 ON THE WATER

Ink & Indie 2026 - Author Signing Event

Mojo Car Show 2026

CrankNCruise Ft. New Impressionz

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

events happening today near me

kent county

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

Dance Conservatory of Maryland presents: June Concert

Elegant Afternoon Tea at Brampton 1860

SINATRA AT THE SANDS with Chris Pinnella

PT. 2 ON THE WATER

PT. 2 ON THE WATER

Ink & Indie 2026 - Author Signing Event

Ink & Indie 2026 - Author Signing Event

Mojo Car Show 2026

Mojo Car Show 2026

CrankNCruise Ft. New Impressionz

CrankNCruise Ft. New Impressionz

Oliver Beach Inn Paint Night

Oliver Beach Inn Paint Night

Needle Felting on the Bohemia - Painting with wool

Needle Felting on the Bohemia - Painting with wool

Rage Box presents: Re: DEFINITION

Rage Box presents: Re: DEFINITION

Bohemia live! Summer Concert Series - Separate Ways The Band

Bohemia live! Summer Concert Series - Separate Ways The Band

Rage Box presents: "Let's Go To The Movies!"

Rage Box presents: "Let's Go To The Movies!"

Fashion in Motion: From City to Runway Brunch & Fashion Show

Fashion in Motion: From City to Runway Brunch & Fashion Show

Rage Box presents: Re: DEFINITION - Division 1, 7-18 yr. olds

Rage Box presents: Re: DEFINITION - Division 1, 7-18 yr. olds

Beginner Yoga Every Tuesday & Thursday

Beginner Yoga Every Tuesday & Thursday

9th Annual Arts, Wine, Jazz & Soul Festival

9th Annual Arts, Wine, Jazz & Soul Festival

SINATRA AT THE SANDS with Chris Pinnella

SINATRA AT THE SANDS with Chris Pinnella

Dance Conservatory of Maryland presents: June Concert

Dance Conservatory of Maryland presents: June Concert

Maryland Crop Scouting School at WYE

Maryland Crop Scouting School at WYE

Elegant Afternoon Tea at Brampton 1860

Elegant Afternoon Tea at Brampton 1860

The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH

The STAR Centre Presents STRAIGHT NO CHASER: BEACH BASH

Bethlehem Church Paint Day

Bethlehem Church Paint Day

Charly's Waterfront Paint Night

Charly's Waterfront Paint Night

Things to do around Chestertown

Trends in Chestertown

1. Chestertown car show

2. Events happening today near me

3. Kent county

4. Yard sales and estate sale

5. Mothers day brunch ballys

6. Garfield theater

7. Chestertown tea party

8. Washington college concert

9. Vendor

10. Schooner sultana

11. Craft fairs

12. Bingo

What are the best events to attend?

Which events are currently trending in Chestertown?

Which events are coming up?