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

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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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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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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CHESTERTOWN, MARYLAND EVENT

PAINT THE TOWN - APRIL 26-29, 2018

Artists from all over the Mid-Atlantic region will paint the local scene during RiverArts annual plein air event, Paint the Town.  Paintings will be available for sale at the RiverArts Gallery. There is a two-hour Quick Draw on Sunday in Fountain Park. More information about the event.  

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Waterfowl Festival | Easton, Maryland
November 10, 11, 12, 2017

An annual event since November, 1971, the wildlife art show, sportsman’s expo celebrates all things “Eastern Shore”. Nationally recognized wildlife artists: painters, sculptors, carvers and photographers will be exhibiting their work in the galleries in historic downtown Easton. Some of the highlights of the festival include the kids fishing derby, art activities, calling contests, retriever demonstrations and DockDogs Competition. For more info visit:  Waterfowl Festival Info

There are plenty of food vendors serving local eastern shore cuisine and a wine & beer tasting pavilion.

And on a special note, Scott Budden will be serving up his Orchard Point Oysters at The Waterfowl

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Date(s):

November 4, 2017 (10:00 am - 4:00 pm)

Overview:

Adkins Arboretum in Talbot County will have five native gardens on the tour, “Celebrating Natives” - highlighting the beauty of native gardens and their importance in creating a biodiverse landscape. The gardens featured in this Talbot County tour display a range of beautiful and creative native plantings. Tickets are $25 in advance and $30 on the day of the tour. Register in advance and save! Link to more information:  Celebrating Fall Gardens

Location:

Adkins Arboretum
Adkins Arboretum
12610 Eveland Rd
Ridgely, MD 21660
(410) 634-2847

 

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CHESTERTOWN DOWNRIGGING WEEKEND

October 27-29, 2017

Visit Chestertown, one of America’s best preserved historic seaports, for Downrigging Weekend - one of the largest annual Tall Ship and Wooden Boat Festivals on the East Coast. In it's 17th year, the festival is organized by Sultana Education Foundation, a non-profit that first formed around the construction of the Sultana. Today, Sultana is a school ship, carrying thousands of children and other passengers on educational trips throughout the year. 

One of the main events is the Fireworks and Ship Illumination on Friday night when all the visiting ships are illuminated. Over the weekend, enjoy performances by world-class musicians; lectures by nationally recognized authors and filmmaker or

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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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Plein Air Easton Art Festival
Easton, Maryland

July 17-23, 2017

The Plein Air Easton Art Festival is the largest and most prestigious juried plein air painting competition in the United States. The week of July 17-23, 2017 there will be 58 competing artists painting throughout Talbot County, Maryland and approximately 6,000-8,000 people participating in the festival throughout the week. 

Contact Info: Plein Air Easton Festival Link   Telephone: 410-822-7297 

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Chestertown's free outdoor concerts will run every other Saturday evening beginning June 24, 2017, from 7-8:30 pm. Chestertown’s “Music in the Park” concert series presents the best in local & regional music – including big band, bluegrass, folk, jazz, rock, and more!

Bring a chair and join the fun in Fountain Park, located in the heart of Historic Downtown Chestertown. The rain location will be Emmanuel Episcopal Church, located directly across the street from the park.  Music in the Park info

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