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Kent County Events in September

September 1, 2018 @ 8:00 am - September 29, 2018 @ 5:00 pm

History Happy Hour

September 7 • 4 p.m.

Bordley History Center, 301 High Street, Chestertown

Historical Society of Kent County hosts an informative history lecture while attendees enjoy a glass of wine. For details, call 410-778-3499.

Chestertown First Friday

September 7 • 5-8 p.m.

Chestertown Historic District

Each month on First Friday, the Downtown Chestertown Association hosts this progressive open house. Businesses keep their doors open later so everyone can enjoy gallery exhibits, unique shopping, special performances, kids’ activities and a variety of dining options. This is one of Chestertown’s most beloved social events. For more information, email downtownchestertown@gmail.com.

Chestertown Farmers’ Market

September 1, 8, 15, 22, 29 • 8 a.m.-Noon

Fountain Park, High and Cross Streets, Chestertown

Find fresh home grown produce, herbs, breads, soaps, plants and cut flowers, as well as the hand-crafted works of local artisans. For details, visit chestertownfarmersmarket.net.

Sultana Public Sail

September 8, 22 • 11 a.m., 2 p.m. September 15 • 2 p.m.

Sultana Education Foundation, 200 South Cross Street, Chestertown

Sultana’s two-hour public sails are a great way to sail the Chester River onboard a traditional schooner. This evening’s sail includes live music by a local artist. Passengers are encouraged to help raise the sails, steer using Sultana’s seven-foot long tiller, and explore the authentically reproduced crew’s quarters below-decks. Call 410-778-6954 to make a reservation.

Young Eagles Day

September 9 • 10 a.m.-2 p.m.

Massey Aerodrome & Air Museum, 33541 Maryland Line Road, Massey

Free airplane rides for young youth from ages 8 to 17. Free hot dogs and hamburgers. The flight is free and flown by a FAA licensed volunteer pilots to introduce youth to the world of flight. For more information, visit masseyaero.org.

“Animal Crackers”

September 14-15, 21-22, 28-29 • 8 p.m. September 16, 23, 30 • 3 p.m.

Garfield Center for the Arts, 210 High Street, Chestertown

Jennifer Kafka Smith makes her directing debut at the Garfield. For details, call 410-810-2060 or email boxoffice@garfieldcenter.org.

Sultana’s Annual Gala

September 15 • 6 p.m.

The Reward, Chestertown

Join the hottest event in town and enjoy great food and entertainment featuring an all illusion show with talented magicians, illusionists and mentalists as well as a DJ and dancing. The annual gala raises money for the Sultana Education Foundation’s award-winning programs in environmental science and American history that serve more than 12,000 students each year. Call 410-778-5954 or email lbrocker@sultanaeducation.org.

Rock Hall Firemen’s Festival

September 15

5K Run/Walk • 9 a.m.

Parade • 10:30 a.m.

Main Street, Rock Hall

Join the fun in Rock Hall for the inaugural Firemen’s Festival 5K Run/Walk starting at 9 a.m. at 21203 Sharp Street. The event benefits the Rock Hall Volunteer Fire Company. Proceeds will create an endowment for the company to help defray the cost of the fire hall. The parade travels along Main Street from Rock Hall Lagoon to Civic Center Drive. For more information, call 410-739-1095.

Block Party

September 15 • Noon-4 p.m.

Cross Street between High and Cannon streets, Chestertown

This fun, new event will happen in the heart of Downtown Chestertown. Enjoy good food, craft vendors, and live music with The Dirty Grass Players. For details, call 443-282-0220.

Cars on High

September 20 • 6-8 p.m.

300 block of High Street by Fountain Park, Chestertown

Classic, exotic, antique and customized cars are on display in the 300 block of High Street. Come admire the rides and chat with the proud owners. Call 410-778-2991 or email CarsOnHighChestertown@gmail.com for all the details. Cars on High will continue on the third Thursday of the month, weather permitting, through October.

Cardboard Boat Race and Waterfront Festival

September 22 • 1-4 p.m.

Wilmer Park, Chestertown

The 12th annual Cardboard Boat Race and Waterfront Festival will follow Washington College’s dedication to the new Hodson Boathouse. The festival, hosted by the college’s Center for Environment and Society, features prizes, food, beer, and live music. Get a ride aboard the college’s research vessel, The Callinectes. Kayaks, canoes, and paddleboards will be available for use through the boathouse. The cardboard boat race will be held at 3 p.m. For more information, call 410-810-7162.

Osprey Triathlon and Fall Festival

September 29 • 9 a.m.-4 p.m.

Kent School, 6788 Wilkins Lane, Chestertown

This family-friendly event welcomes athletes of all skill and experience, ages nine and up. The event will include a One Mile Fun Run for all ages and fun activities for the whole family. The triathlon consists of a seven-mile bike race, a two-miles kayak course and a three-mile run. Call 410-778-4100 x350.


September 1, 2018 @ 8:00 am
September 29, 2018 @ 5:00 pm


Kent County, Maryland
Chestertown, MD 21620 United States + Google Map
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