Things to Do IN CHESTERTOWN

Welcome to Chestertown! Check out the latest events in town. Explore by location, trending searches, top organisers, and more. Whether you're a local, new to the area, or cruising through, there's no shortage of unique things to do.

Chestertown's top activities

Your plans, made easy. Check out the most popular things to do in Chestertown.

Oysters and Indians Public Paddle - 2025 - Sultana Education Foundation

Sat, May 31, 10:00

Stillpond Creek • Chestertown, MD

Starts at $49.30

Sultana Education Foundation Public Paddles

278 followers

Adventurous Scavenger Hunt! - Centreville‘s Quaint Quest

Today at 08:00 + 288 more events

305 Chesterfield Ave • Centreville, MD

Starts at $14.99

Let's Roam Scavenger Hunt Adventures

5k followers

Tour of the Tanks

Today at 16:00 + 3 more events

237 Bohemia Manor Farm Ln • Chesapeake City, MD

Starts at $33.85

Bohemia Manor Farm

250 followers

ITCH Career Club - Chestertown

Thu, Feb 20, 18:30 + 4 more events

University of Maryland Shore Medical Center at Chestertown • Chestertown, MD

Free

Dr. Judi Gieske

Noises Off!

Fri, Feb 21, 20:00 + 10 more events

Garfield Center for the Arts at the Prince Theatre • Chestertown, MD

Starts at $12.51

Garfield Center for the Arts

244 followers

March Madness WarmUp!

Sat, Mar 1, 20:00

Minary’s Dream Alliance, Inc. • Chestertown, MD

Starts at $12.51

Force One Productions

Chestertown Office Open House

Thu, Mar 20, 16:30

315 High St suite 202 • Chestertown, MD

Free

For All Seasons

119 followers

A Talk about ADHD & Anxiety with Dr. David Palmiter - Community Event

Wed, Mar 26, 17:30

Radcliffe Creek School, Talbot Boulevard, Chestertown, MD, USA • Chestertown, MD

Free

Radcliffe Creek School

Chestertown's top activities

Your plans, made easy. Check out the most popular things to do in Chestertown.

Oysters and Indians Public Paddle - 2025 - Sultana Education FoundationOysters and Indians Public Paddle - 2025 - Sultana Education Foundation

Adventurous Scavenger Hunt! - Centreville‘s Quaint QuestAdventurous Scavenger Hunt! - Centreville‘s Quaint Quest

Tour of the TanksTour of the Tanks

ITCH Career Club - ChestertownITCH Career Club - Chestertown

Noises Off!Noises Off!

March Madness WarmUp!March Madness WarmUp!

Chestertown Office Open HouseChestertown Office Open House

A Talk about ADHD & Anxiety with Dr. David Palmiter - Community EventA Talk about ADHD & Anxiety with Dr. David Palmiter - Community Event

Oysters and Indians Public Paddle - 2025 - Sultana Education Foundation

Adventurous Scavenger Hunt! - Centreville‘s Quaint Quest

Tour of the Tanks

ITCH Career Club - Chestertown

Noises Off!

March Madness WarmUp!

Chestertown Office Open House

A Talk about ADHD & Anxiety with Dr. David Palmiter - Community Event