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Upcoming Events at Great Oak Manor and in Kent County:

First Friday – March 2
Enjoy Chestertown after dark! Visit the gallery exhibits and unique shops, watch special performances, participate in kids’ activities and enjoy a variety of dining options. 

Pizza Night at Crow Vineyards – March 10
Enjoy a variety of handmade artisan pizzas made using fresh ingredients paired with Crow Vineyard wine.

Bourbon and Cigar Weekend – March 9-11
Enjoy a weekend filled with bourbon and cigars! The weekend will include a bourbon pairing dinner on Saturday. More details to come!

Kent Ag Auction – March 17
This annual fundraiser benefits the Kent Ag Center facility and the Kent County Fair. The event includes a silent and live auction with many donated items from local businesses, artists and supporters.

World Music Concert – March 22
Washington College’s Department of Music presents a world music concert, featuring a Japanese Ensemble, an Afro-Cuban Ensemble, and a Pan Pipe Ensemble.

Recycled Runway – March 24
Chestertown RiverArts is sponsoring the first annual Recycled Runway, an upscale fashion show featuring fabulous, one-of-a-kind creations designed by artists and groups of all ages using recycled or re-purposed materials. The evening will also feature a silent auction. Cash bar. 

Resonance (formerly Kent County Chamber Music) – March 25
One of six high-quality chamber music performances in our community!

Easter Weekend – March 30-April 1
Spend your long Easter weekend or spring break at Great Oak Manor, relaxing in a hammock, watching the flowers bloom, or dipping your toes in the Chesapeake Bay!

Chestertown First Friday – April 6
Enjoy Chestertown after dark! Visit the gallery exhibits and unique shops, watch special performances, participate in kids’ activities and enjoy a variety of dining options. 

Art of Stewardship – April 6-28
Each April, Chestertown’s RiverArts celebrates the community’s long tradition of environmental conservation by hosting The Art of Stewardship Exhibition. Artists and poets are invited to submit work that reflects a moment, experience, realization or vision of nature that inspires a new outlook or reflects on the theme of “Convergence at the Edges.” 

Community Day – April 14
A family-friendly event and block-party that features food, art, crafts, musical performances, children’s activities, and more. This event will allow attendees to learn about what both Chestertown and Washington College have to offer.

Taste of Rock Hall – April 21
At the kick-off for Rock Hall Restaurant Week sample a variety of specialties from local restaurants and enjoy live and silent auctions.

Washington College Piano Festival – April 21
The Washington College Piano Festival invites participants of all ages to further develop their talents in an immersive educational experience. Students will have the opportunity to attend workshops, take lessons, and compete and win prizes in the Washington College Piano Competition, including the chance to perform in Hotchkiss Recital Hall. Featured guest artist, Lydia Artymiw, Distinguished McKnight Professor of Piano at the University of Minnesota, will be teaching a master class and presenting a concert as part of the Washington College Premier Artists Series. 

For tickets to Lydia Artymiw’s performance, click here.

Rock Hall Restaurant Week – April 22-28

Sweeny Todd – April 27-May 13
Come see the Barber of Fleet Street!

Draw for Sight Bicycle Ride & Poker Run – April 29
Choose from 36 or 60 mile rides. The ride starts at Betterton Fire Hall, goes through Historic Chestertown, and through the beautiful countryside in Kent County. Participants will draw cards at various stops. Prizes are awarded to the top 10 poker hands. Registration required.

Call now to book your wonderful getaway in Kent County, MD!

Host Your Special Event at Our Manor on the Chesapeake Bay

It’s no doubt that Great Oak Manor is the perfect setting for a panoramic Eastern Shore wedding, but our slice of the Chesapeake is the ideal venue for any event you might be planning. Consider booking a family reunion, hunting party, yoga retreat, murder mystery party, or a dinner party. We even host corporate events as there are plenty of rooms and spaces for meetings. No matter what you’re planning, you’ll want it to be extraordinary, so why not choose a location that will be equally as memorable? Send an email to  for more information.