THE BEST OF CHESTERTOWN

Make the Most of Your Visit

YOUR GUIDES TO CHESTERTOWN & KENT COUNTY

Start at the Visitor’s Center!

Chestertown Visitor's Center Exterior a Brick Building

THE GATEWAY TO CHESTERTOWN

Welcome to the Chestertown Visitor’s Center, your gateway to all that our charming town has to offer. Stop by to pick up maps, brochures, and insider tips from our friendly staff. Discover the best places to dine, shop, and explore, and learn about upcoming events and attractions. Whether you’re a first-time visitor or a seasoned traveler, the Chestertown Visitor’s Center is here to help you make the most of your visit.

Things to Do

Child looking outside the shop in downtown Chestertown

SHOPPING

Discover unique treasures, household goods, and much more with our locally owned downtown shops.

Customers dining outside in front of the Kitchen in Chestertown, Maryland under an umbrella table

DINING

From artisan pizza, award winning Maryland crab cakes, and so much more, Chestertown's downtown dining always hits the spot.

EXPERIENCES

Experience everything Chestertown and Kent County has to offfer from lectures at Washington College to kayaking the Chester River.

Front of The White Swan Tavern Downtown Chestertown

ACCOMMODATIONS

Downtown Chestertown offers many choices for our out of town visitors, including a newly renovated downton inn, classic Bed and Breakfasts, and many Air BnB's. .

SERVICES

Explore the many services Chestertown and Kent County have to offer.

EVENTS

From our Signature Events like the Chestertown Tea Party and Dickens Festival to recurring events like First Friday, Chestertown is a great weekend getaway.

Upcoming Events

Chestertown is known for some long standing popular events that draw visitors from around the world! Enjoy Chestertown's year-round festivities from the weekly Farmers' Market to our Dickens of a Christmas in December! Join us for our next event, we promise good entertainment, good refreshments and great people!