Plan your trip early and stay in Chestertown! Click here for local lodging.

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Recurring

Utilities Commission Meeting

Town of Chesterotwn 118 N. Cross Street, Chestertown, MD

3/28/2022 - Town Council meetings will now start at 6pm CLICK FOR TOWN AGENDAS & MINUTES

8th Annual Backyard Bash

Recovery In Motion 300 Scheeler Road, Chestertown, MD

Free family fun event! There will be plenty of great resources, door prizes, giveaways, free food and more! Our goal is to support the Community and YOU! Parties

Recurring

Planning Commission Meeting

Town of Chestertown 118 N. Cross Street, Chestertown, MD

Any member of the public wanting to join the Zoom meeting should contact Kees de Mooy at 410-778-0500 or kees@chestertown.com CLICK FOR TOWN AGENDAS & MINUTES

Cars on High

Main Street Chestertown - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Father's Day Cruise on the River Packet

River Packet - High Street Town Dock

Gather your family and friends for a Father's Day brunch cruise aboard the River Packet! Reservations are required - click the link for more information and to reserve your tickets.

Carnival On High

Downtown Chestertown

Main Street Chestertown’s newest event… Carnival On High! Balloon animals, face painting, cotton candy, train rides, games & prizes! Mark your calendar, more updates to come! Food, drinks, beer &… Continue Reading Carnival On High

Kent County Waterman's Day

Rock Hall Bulkhead

We are back in action!Join us on Sunday, July 3rd for our annual family fun day of food, contests, vendors and the beloved boat docking!

Recurring

Kent County Fair

Kent County Fairgrounds - 21349 Tolchester Beach Rd, Chestertown, MD 21620 - Kent County Fairgrounds - 21349 Tolchester Beach Rd, Chestertown, MD 21620

The Kent County Fair is a county fair featuring great food, 4-H and community exhibits, animals, tractors, games and entertainment. The focus of the fair is agricultural education and providing… Continue Reading Kent County Fair

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Recurring

Crazy Days

Downtown Chestertown

Downtown Chestertown’s annual sidewalk sale, Crazy Days, begins on Thursday, July 28 and runs through Saturday, July 30, with many stores carrying the specials into Sunday. This summer tradition is… Continue Reading Crazy Days

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Chestertown Art Walk

Chestertown A&E District - Downtown Chestertown

Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants and around town. Live music will also… Continue Reading Chestertown Art Walk

Chestertown Car Show

Downtown Chestertown - High Street, Chestertown - Downtown Chestertown - High Street, Chestertown

Register your own pride and joy to compete for trophies, or just stroll the street to admire what other auto enthusiasts have brought to display, from custom hotrods to classic… Continue Reading Chestertown Car Show

Touch A Truck Ag Fest

Kent County Ag Center - 21349 Tolchester Beach Rd, Chestertown, MD 21620

Come out to the Ag Center and explore emergency vehicles, construction and farm equipment, trucks and more! Fun Family Event!

Recurring

HP Fest

Downtown Chestertown-Various - 200 Block of High Street

A Weekend of Magic: Grab your wand, hop on your broom, and come for a weekend of magic at the fifth annual Chestertown HP Festival. Explore our colonial river town… Continue Reading HP Fest

Cars on High

300 High Street - Fountain Park

Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October.

Festival Grand Opening

Raimond Cultural Center - 101 Spring Avenue - Raimond Cultural Center - 101 Spring Avenue - Raimond Cultural Center - 101 Spring Avenue - Raimond Cultural Center - 101 Spring Avenue

A Festival Grand Opening of the Kent Cultural Alliance's new home, the Vincent and Leslie Prince Raimond Cultural Center. Music, art, food trucks, and celebration More INFO soon. Times shown… Continue Reading Festival Grand Opening

Recurring

Dickens of a Christmas 2022

Chestertown Historic District - 200 block High Street

Chestertown's Dickens-inspired holiday festival returns with more street performers, live music, food and drink, carriage rides, and more! For a full schedule, ticket sales, and more information, visit https://mainstreetchestertown.org/dickens/

Chestertown Art Walk

Chestertown A&E District - Downtown Chestertown

Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants and around town. Live music will also… Continue Reading Chestertown Art Walk

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