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CHESTERTOWN DOWNRIGGING FESTIVAL - October 29 - 31, 2021

Visit Historic Chestertown, one of America's best preserved historic seaports, for Sultana Education Foundation's Downrigging Weekend Festival. Today, Sultana is a school ship, carrying thousands of children and other passengers on educational trips throughout the year. 

Chestertown's Downrigging Weekend is one of the largest annual Tall Ship and wooden boat festivals on the East Coast. Enjoy performances by world-class musicians; lectures by nationally recognized authors and filmmakers. Go sailing as part of a fleet of historic ships", representing over 400 years of maritime history. For a Schedule of Events and more info visit Chestertown Downrigging Festival

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Perched on the river bank, this beautiful home enjoys broad views of the Chester River and vistas of expansive marshlands. Designed by local architect Peter Newlin, FAIA, the home offers architectural elements such as a curved stair with skylight and free-standing fireplace. The open floor plan and expansive windows exude warmth and comfort accentuated by captivating river views. Set in Queen Anne’s County Maryland, the home is a 4-mile drive or quick boat ride to historic Chestertown. Founded in 1706, and home to Washington College, Chestertown is a lovely waterfront town with brick sidewalks, shops, restaurants, parks, marina, oyster bar and cafes. It is about 90 minutes from Washington, D.C. and Philadelphia.  Offered at $887,000. 

 

          

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Just outside of Rock Hall is Eastern Neck National Wildlife Refuge. The 2,285-acre island refuge is a major feeding and resting place for migrating and wintering waterfowl.  Walk along seven different trails and boardwalks for great wildlife viewing and expansive views of the Chester River and Chesapeake Bay. The Visitor Contact Station is staffed daily by volunteers. Link for more information Eastern Neck National Wildlife Refuge.  
More trip ideas can be found at  https://www.findyourchesapeake.com  

For those wandering around and feeling like some fresh oysters... you may want to checkout Scott's website Orchard Point Oysters 

 

 

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Eastern Shore 45-acre Certified Organic Farm is just 5-minutes from the Chesapeake Bay in a peaceful, private rural landscape. The farm has a pond, livestock, alfalfa and corn, and offers 35 acres of pasture, 7-acres of woods, two barns and a shed. Convenient features include two separate first floor living areas. The main living space offers a recently updated kitchen, great room, master suite, office, bedroom and family room.  Located in Kent County, Maryland, just 10-minutes from Historic Chestertown set on the banks of the Chester River. Located about 90 minutes from Philadelphia and Washington, D.C. Link to more information and photos.  Listing offered at $895,000.  

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Dickens of a Christmas in Chestertown, December 6-8, 2019

The third annual Dickens of a Christmas is a fun weekend of Christmas events, folks in period dress and live music. House tours, carriage rides and High Tea are among the festivities, as well as a London Row of vendors selling handcrafted goods. Hot beverages and shops with refreshments add to the holiday merriment. 

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215 N. Kent Street Chestertown

Charming Eastern Shore Home - Built in 2011

New Listing - Richard Budden, Realtor

Eastern Shore cottage style home was built in 2011 and is nestled in the Chestertown Historic District. The home offers off-street parking and a finished basement. Convenient location is a walk away from Washington College, the Chester River Walk and downtown Chestertown shops, galleries, restaurants and cafes. Well cared-for home has an open floor plan invoking a casual ambiance. The bright, spacious kitchen has countertop seating and a dining area that opens to the deck and a peaceful view of woods and plantings. Link to more information and large photos.  Offered at $342,000.  

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Crow Vineyard & Winery

Wine & Oyster Pairing Event

Saturday, March 9, 2019

1:00 pm - 4:00 pm

Crow Vineyard is hosting a local pairing of award-winning Crow wines and oysters from Orchard Point Oysters *  The pairing includes a tasting of 3 wines and 3 oysters as well as samples of local Eve’s Cheese and Crow grass-fed Angus beef. Additional wine and oysters, raw or grilled, will be available for purchase. Link to more information: Crow Vineyard Wine Pairing Event

Award Winning Crow Vineyard & Winery is also a lovely Farmstay B&B.  Guests can enjoy wine tastings, farm-to-table experiences and other events. The winery is located in Kennedyville on the Eastern Shore of Maryland, just north of Chestertown.

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 Eastern Shore B&B for sale

Savor the rich history of Brampton Inn. Set on 20 acres, the beautifully restored 1860 Eastern Shore manor house offers gracious hospitality and 13 ensuite refined lodgings in both the Inn and other cottages on the property. The Inn, a Select Registry property and rated #1 on Trip Advisor, is conveniently located just 2-miles from historic Chestertown. Brampton is a strong, viable business and is offered by its owner of over 30 years as a turnkey operation. Also for sale is an adjacent home built in 2003 set on 10-acres and an additional 5-acre parcel. The property is being offered for $2,495,000.  Link to photos and information  Brampton Info 

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Chestertown Tea Party Festival | Friday-Sunday May 25-27, 2018

The Annual Chestertown Tea Party Festival will be underway this Memorial Weekend, beginning Friday. 

NEW THIS YEAR!  Thanks to the efforts of Kelly Distributors, the famous Budweiser Clydesdales will be present. They will make their first appearance at the Friday evening Street Party at the foot of High Street.

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 Colonial Parade starts at 10:00 and at 2:00 the reenactment of the 'Tossing of the Tea

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