Explore the Eastern Shore - Events and Things to Do RSS Icon

The Eastern Shore offers many diverse areas to discover and activities to enjoy. The Chesapeake Bay, Chester River and other waterways provide natural settings to enjoy the ever-changing landscapes and wildlife. The Eastern Shore is popular for hunting, biking, fishing, oysters, crabs and boating activities.

Historic Chestertown is a great destination for a day trip or weekend getaway at a local B&B or Inn. Enjoy the Chester River Walk, shops, cafes and the many parks and walking trails. The historic fishing village of Rock Hall offers canoe rentals and boat charters. Annual Eastern Shore events include the Chestertown Tea Party, Sultana Downrigging Festival and the Easton Wildlife Festival.

Visit our site for local information about the area and communities. 

Found 102 entries about Explore the Eastern Shore - Events and Things to Do.

SIGNIFICANTLY REDUCED! Waterfront Eastern Shore cottageis nestled on Phillips Creek. A perfect vacation home, it is privately sited with serene waterviews and is in perfect harmony with its naturally beautiful setting. Cathedral ceiling, fireplace, wood floor and trim add to the charm; while the screened porch and deck are quiet spots for outdoor entertaining. Chestertown is about 1-hour from Annapolis and Wilmington.  REDUCED TO:  $499,000.  Link to more Photos and Info: 24249 Walnut Point Road

Eastern Shore Cottage

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EASTERN SHORE - CHESTERTOWN

WINTERFEST WEEKEND

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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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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Fall Open House
Adkins Arboretum Native Plant Nursery
September 13th and 14th, 2014

The Arboretum offers the largest selection of native plants for the Chesapeake Gardener. In addition to the native plant sale, visitors can tour the Nursery. There will be music performances, informative programs and discount coupon toward the purchase of native trees.  Adkins Arboretum is located at:  12610 Eveland Road, Ridgely, Maryland.  For more information call 410-634-2847 or visit www.adkinsarboretum.org

 

 

 

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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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The 3rd Annual Great Chesapeake Balloon Festival will be held:

Friday & Saturday, August 1 & 2, 2014

The Easton festival will feature many events including at least 15 balloons and a giant walk-thru balloon for children and adults.  Two hot air balloons, tethered to the ground will offer rides up to 60 feet in the air.  After Sunset there will be a balloon 'glow'.  Premiering this year is a special shape balloon, “Eddie &  Rickenbacker” balloon featuring the history of Army aviation.  Visit this link for additional info More Balloon Festival

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War of 1812 Battle of Caulk's Field
Bicentennial 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 Bicentennial Re-Enactment is scheduled to take place on the original battlefield site located in Kent County, Maryland.  Read more Battle of Caulk's Field.  This is a 2-day event with plenty of things to do around Kent County.  Besides the actual re-enactment other planned activities include:  Tall Ship public sails and tours, parades, re-enactments, and dedications.

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

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CHESTERTOWN CRAZY DAYS

Thursday July 24 - Saturday, July 26

Chestertown’s annual Crazy Days event is this week!  The main focus is on the downtown shops having their sidewalk sales.  In Fountain Park kids can enjoy free face painting, story telling with local Playmaker's group, and watch a Pie Eating Contest.

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