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What's Up Magazine

Chestertown Save-the-Date Events

Oct 13, 2017 09:00AM

Quality of life in Chestertown includes vibrant theatre productions, comedy nights, and theatre programs for children at the historic Garfield Center. Photo by Jeff Weber

Plan your trip to Chestertown ahead of time with this annual schedule of their must-attend events.


Weekly Events

Farmer’s Market, Saturdays, 8 am-noon, Fountain Park

River Arts, KidSPOT, Saturdays, 9 am-noon, creative activities, ages 2-12

Annual Events check websites for 2018 event dates

April – Paint the Town: Artists from mid-Atlantic region come together for a fun weekend.

May – Taste of the Town: Chefs, farmers, winery owners celebrate good taste. Fountain Park.

May – Porch Fest: Local musicians provide the sound track for an event unique to Chestertown.

Memorial Day Weekend – Chestertown Tea Party Festival: a rollicking recreation of Chestertown’s resistance to British oversight.

June – National Music Festival brings together mentors and qualified young musicians from around the world for two weeks of rehearsals and concerts.

June – Bay-to-Bay Cycle Ride: choose one of five routes, 27-104 miles long.

July 4 – Independence Day Fireworks Over the Chester River

August – Legacy Day/Music in the Park. Parade, street dancing, multi-cultural displays.

September – Chestertown Jazz

October 6-7– Chestertown Harry Potter Festival: Fourth annual town-wide celebration marks 20th anniversary of first Harry Potter book. Costume contests, Hogwarts classes, parties and more.

October 7 – Historic House Tour: See a dozen exquisite homes.

October 28-31 – Sultana Downrigging Tall Ship & Wooden Boat Festival: Spend the weekend as part of one of the largest annual Tall Ship gatherings on the East Coast.

October 28 – Halloween Parade: Come for the morning; spend the day.

November 24: Santa’s Arrival & Town Lighting: A family tradition that illuminates Chestertown’s Historic District and ushers in the holiday season.

November 25 – Holiday Parade: A Saturday morning of marching bands, floats, and fun.

November 25-27 – Antiques Show & Sale at Washington College to benefit a therapeutic horseback riding program for the disabled.

December 1-3: Winterfest: A Dickens of a Christmas! Chestertown goes all out to provide a memorable holiday weekend for all ages.

NOTE: The River Packet offers sunset cocktail and dinner cruises spring through late fall. It’s a great way to see Chestertown’s historic waterfront estates and the natural landscapes bordering the Chester River.