Chestertown Tea Party Festival | Friday-Sunday May 26-28, 2023

The Annual Chestertown Tea Party Festival will be underway this Memorial Weekend, beginning Friday. The Festival commemorates events that took place in 1774. According to local lore, on May 23rd, 1774, the citizens’ of Chestertown gathered at the town center, marched down High Street to the brigantine Geddes, and tossed her cargo of tea into the Chester River. 

On Saturday the main events are the Colonial Parade at 10:00 and at 2:00 the reenactment of the 'Tossing of the Tea Overboard' on the Chester River begins.  On Sunday, the zany Annual Raft Race is at 2:00 where home-made rafts provide plenty of entertainment trying to win the trophy "Tea Cup". 

During the day Saturday,

The Chestertown area has many outdoor activities to enjoy and places to explore. One of the most important resources for individuals and families is the Sultana Education Foundation (SEF),  offering a virtual classroom, programs and outdoor experiences for the public. 

CHESTERTOWN, MARYLAND EVENT

PAINT THE TOWN - APRIL 26-29, 2018

Artists from all over the Mid-Atlantic region will paint the local scene during RiverArts annual plein air event, Paint the Town.  Paintings will be available for sale at the RiverArts Gallery. There is a two-hour Quick Draw on Sunday in Fountain Park. More information about the event.  

CHESTERTOWN DOWNRIGGING WEEKEND

October 27-29, 2017

Visit Chestertown, one of America’s best preserved historic seaports, for Downrigging Weekend - one of the largest annual Tall Ship and Wooden Boat Festivals on the East Coast. In it's 17th year, the festival is organized by Sultana Education Foundation, a non-profit that first formed around the construction of the Sultana. Today, Sultana is a school ship, carrying thousands of children and other passengers on educational trips throughout the year. 

One of the main events is the Fireworks and Ship Illumination on Friday night when all the visiting ships are illuminated. Over the weekend, enjoy performances by world-class musicians; lectures by nationally recognized authors and filmmaker or

Eastern Shore
Artists Studio Tour
Chestertown, Maryland

October 22-23 and October 29-30, 2016

The Chestertown Annual Artists Studio Tour offers the works of over 45 artists and will be running for two weekends, Oct 22-23 & Oct 29-30.A sampling of the artists work is available for viewing at the RiverArts Gallery at 315 High Street, Suite 106, Chestertown.  One of the studios not be missed is the artist Jennifer Deskins.  More info on the Studio Tour at  Chestertown RiverArts Studio Tour

Chestertown Harry Potter Festival
September 30 – October 2, 2016

The weekend festival celebrates the spirit and theme of Harry Potter, while promoting the town’s local community and its arts. Theme-decorated downtown shops will host an all day scavenger hunt and other activities include a Potions Class, costume contest and “Hogwarts Experience” at The Garfield Center for the Arts. The DC Quidditch Club will host a two-day tournament with teams competing for the cup. For more information and tickets visit these links: Harry Potter Festival Info    Garfield Center for the Arts

Chestertown Jazz Festival 2016
Thursday, Sept 8 through Sunday, Sept 11, 2016

The Chestertown Jazz Festival for 2016 will be in full swing from Thursday, September 8 through Sunday September 11, 2016.  The artists Lineup includes: Gregor Huebner jazz quarter- El Violin Latino; Lena Seikaly from Washington, D.C., The Greg Hatza Organization; Giacomo Gates, and Chuck Redd & La Lucha.  Enjoy concerts, local food vendors and wine tastings!