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Found 44 blog entries tagged as Things to Do.

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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Chesapeake Bay Balloon and Wine Festival

August 4-5, 2017

Triple Creek Winery, Cordova Maryland

The festival will feature 19 Hot Air Balloons offering passenger flights, tethered balloon rides and a Junior Balloonist Camp for kids.  There will be vendors for crafts and food and a Roaming Railroad will provide rides for kids and adults.  More information can be found on their website  Chesapeake Bay Balloon & Wine Festival


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Annual RiverArts Holiday Show & Sale
November 17 - December 31, 2016

Chestertown is a unique destination to embark on Christmas shopping and holiday cheer. Walk the tree-lined brick streets and visit gift shops, clothing stores, galleries, bakery, coffee shop and restaurants. Stroll down to the town landing and walk along the Chester River Walk.  The RiverArts studio offers an array of artwork, pottery, textiles and other beautiful finds. Web Link to plan a visit  Chestertown Information.






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Pirates & Wenches Fantasy Weekend
Eastern Shore Event - Rock Hall, Maryland
  August 12-14, 2016

Rock Hall Pirates and Wenches boat

Kids and adults alike will enjoy The 9th Annual Rock Hall Pirates and Wenches Festival! Activities and events include a Decorated Dinghy Contest, Rum Tasting, Treasure Hunt, Wine Tasting, Caribbean style beach party and Pirate, Pets and Kids Costume Contest, and the Buccaneer's Ball.

Live music, street performers, craftspeople and food vendors will be aplenty. For the Event Schedule and more information visit this link  Pirates & Wenches Fantasy Weekend

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Birding Weekend
Chesapeake Bay Environmental Center
Saturday-Sunday June 11 & 12, 2016

Eastern Shore Event!  The Chesapeake Bay Environmental Center in Grasonville, Maryland is home to 230 different species of birds, numerous trails and waterways. Activities include a slow boat excursion of osprey nests, walks with ornithologists, workshops and a photography field trip.  A Schedule of events and more information is available at this link  Birding Weekend Info


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DECEMBER 5-7, 2014

Downtown Chestertown is hosting various holiday themed events throughout Chestertown this weekend.  Children's activities include Santa's Workshop, Ghost Stories of Historic Kent County, Toy Train and Model Railroad Exhibit at Kent County Public Library, and Colonial Crafts for Kids.

Also planned is the Colonial House Tour, Chester River Chorale Holiday Concert, Music at Fountain Park, and wine tastings.  Visit Winterfest Weekend Website for the complete schedule More Info Winterfest 

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Sale of the remodeled 4-bedroom home includes a separate adjacent building lot. The cottage, 2-blocks from Betterton Beach and the Chesapeake Bay, offers glimpses of the Bay during the Winter months. Features include vinyl siding, a new deck and kitchen updates. The historic town of Betterton has a rich history and is 30-min. from Middletown, DE and 20-min. from historic Chestertown, MD.  Link to more information and photos:  More 14 1st Avenue

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Annapolis U.S. Sailboat Show
October 9th through October 13th, 2014

Now in it's 43rd year, the internationally acclaimed sailboat show at Annapolis City Dock is the largest and oldest in-water sailboat show in the world.  Sailboats from major manufacturers include new designs and models make their debut. Explore all designs including the world's largest collection of catamarans and multihulls.

Miles of docks are constructed to display everything from brand new cruising sailboats to kayaks, paddleboards, and canoes. - See more at: https://www.annapolisboatshows.com/united-states-sailboat-show/?q=us-sailboat-show/home#sthash.I3I7SaaN.dpuf

The historic seaport of Annapolis has miles of docks constructed to display everything from kayaks, paddleboards

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War of 1812
Battle of Caulk's Field Re-enactment
Chestertown, MD

Saturday, August 30, 2014 - Activities Throughout Kent County
Sunday, August 31, 2014–The Re-enactment at Caulk's Field Battlefield

The Battle of Caulk’s Field took place in the night of Aug. 30 and early morning hours of Aug. 31, 1814, during the week between the burning of Washington and the attack on Fort McHenry. During that time the British navy had the task of blockading American shipping on the Chesapeake Bay, transporting Royal Marines and sailors to points of attack, and using a fleet of battle-rigged ships of the line to harass and disrupt American military, commerce and regular citizens. Read more Battle of Caulk's Field.

The Battle of Caulk’s Field Bicentennial

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