Happening Next in Chestertown

Name: Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm
Start: 2025-10-31
End: 2025-10-31
Location: Chestertown Marina

Upcoming Events in Chestertown

Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm

Chestertown Marina 1 Nov 2025

USD 40 TO 71

Eastern Shore Life Artist Talk

343 High St, Chestertown, MD 21620-1316, United States 10 Oct 2025

ART

Kids' Nights: Craft Night (Ages 5-11)

151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620 10 Oct 2025

KIDS

October Permaculture Potluck

23963 Walnut Point Rd, Chestertown, MD 21620-5236, United States 26 Oct 2025

FOOD-DRINKS

Kids' Nights: Halloween Movie Night (Ages 2-11)

151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620 24 Oct 2025

HALLOWEEN

BINGO DISCO

Minary’s Dream Alliance, Incorporated 8 Nov 2025

PARTIES

Trunk or Treat

High St, Chestertown, MD 21620, United States 25 Oct 2025

TRUNK-OR-TREAT

Washington College Field Hockey Fall Prospect Day

Washington College 18 Oct 2025

SPORTS USD 87

Pop-Up Vinyasa: The Life of a Showgirl

932 Washington Avenue, Chestertown, MD, United States, Maryland 21620 10 Oct 2025

POP-UPS

Kids' Nights: Music Exploration Night (Ages 2-11)

151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620 21 Nov 2025

KIDS

Ken Miller Performing at Riley's Mill Ale Works

Riley's Mill Ale Works 28 Nov 2025

ENTERTAINMENT

Phat Daddy’s BBQ & Catering

205 Spring Ave Chestertown,Md 21620 11 Oct 2025

MUSIC

Haunted Heat: Pop-Up Power Flow

932 Washington Avenue, Chestertown, MD, United States, Maryland 21620 17 Oct 2025

POP-UPS

GCA's The Kitchen Sink of HORRORS

Garfield Center for the Arts at the Prince Theatre 25 Oct 2025

CONTESTS USD 29

Ashley Chapa Acoustic Duo & Woody’s Goodies Food Truck

860 High Street, Chestertown, MD 11 Oct 2025

FOOD-DRINKS

Shore ‘Nuff Band & Woody’s Goodies Food Truck

860 High Street, Chestertown, MD 10 Oct 2025

MUSIC

Free Community Meditation

932 Washington Avenue, Chestertown, MD, United States, Maryland 21620 1 Nov 2025

HEALTH-WELLNESS

WC Film Series/ Cool Hand Luke

300 Washington Ave, Chestertown, MD, United States, Maryland 21620 6 Nov 2025

ENTERTAINMENT

Kids' Nights: Holiday Movie Night (Ages 2-11)

151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620 5 Dec 2025

KIDS

Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm

Chestertown Marina 31 Oct 2025

USD 49 TO 71

More things to do in Chestertown