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.

Come by land or sea wth the kids for some fun.  Rock Hall is sponsoring its 4th annual Pirates and Wenches Weekend, August 12-14, 2011.  There will be kids' games, a pirate encampment, storytelling, artisans, boat races and beach party.  The Inn at Osprey Point is hosting a Rum Tasting and Bay Wolf Restaurant will be having a Sing-A-Long. For more information, visit the website Rock Hall Pirates.

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Chestertown's Crazy Days is being held this week - July 28-30.  The annual event is basically a sidewalk sale with some fun activities thrown in.  A fun day to be out and about.  Somehow I always come away with a few 'finds'.  VB

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When I was growing up, a nice summer Saturday evening held great promise for me and my brothers.  If we were lucky, Mom and Dad might be taking us for our big outing to the Drive-in to see the latest Disney or John Wayne movie.  It was always an adventure.  First you had to find a speaker that worked which meant you got to ride up and down the rows until Dad found a suitable spot at just the right angle.  Then the trip to the Concession Stand - holding your snacks and trying to find your car again was always a challenge. It was great fun - just something about being in your PJs in the back seat in the dark with a speaker squawking in the window and the huge movie screen looming up ahead. 

We don't have a drive-in handy in Kent County, but you can

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Tea Party Boat

Chestertown will be hosting the annual Chestertown Tea Party Festival this weekend, May 27-29.  The festivities include craft vendors and demonstrations, singing, dancing, wine tastings, folks dressed in period costume, and of course plenty of Eastern Shore fare to taste.  The main attraction is the reenactment of the Tea Toss which originally occured in May 1774.  Rowdy Chestertown residents gather at the town center, then make their way down to the Chester River, where they row out to the ships to 'toss the tea'.  Other activities include a colonial parade on Saturday and a Raft Race on Sunday.  Admission is free.  For more information, visit the official website:  Chestertown Tea Party

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The 74th Annual Maryland House & Garden Pilgrimage will include a walking tour of Chestertown in Kent County, Maryland on  Saturday, May 14, from 10am-5pm.  The Maryland House and Garden Pilgrimage (MHGP), a non-profit organization, is dedicated to the preservation and restoration of architecturally significant properties in the State of Maryland. The Pilgrimage has remained constant with this purpose since its formation in 1930.

Chestertown's 4-block walking tour of historic properties and gardens include: Emmanuel Church, c. 1767, The Geddes-Piper House, c. 1784, The Houston House & Garden, N. Queen St, C. 1771, The Nicholson House and Garden, N. Queen St., C. 1788, The Wallis-Wikes House and Garden, High St., c. 1780, The Sarvis House and

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The 4th Annual Taste of the Town will be held this Sunday, May 1, 2011 from 12:00 - 3:00 PM.  The new venue is in Fountain Park in downtown Historic Chestertown.  Enjoy sample signature dishes from a wide variety of Chestertown restaurants, as well as local wines and beers.  Some of the cooking participants include:  Against the Grain, Brooks Tavern, Fish Whistle, Imperial hotel, Inn at Osprey Point, Lemon Leaf Cafe, Lusia’s Cafe, New York Kosher Style Deli, Procolino’s Italian Eatery, Play it Again Sam, and Two Tree Restaurant.  Wines will be available from St. Michaels Winery and beers from 16 Mile Brewery.  For more information visit Taste of Chestertown

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It is great to have the new bakery in downtown Chestertown.  Against the Grain recently opened its doors in downtown Chestertown.  Douglas Rae, Head Baker, specializes in artisan breads and pastries crafted in the European tradition. They are now also open for lunch with sandwiches and soup on the menu.  For hours and more information, visit their website Against the Grain Bread Co..

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The Chestertown Farmers' Market is an important part of welcoming Spring! The Market is famous for its Saturday Market but is also open on Wednesdays.  Located in Fountain Park in the middle of Historic Chestertown, you can visit Saturday  8:00 am - 1:00 PM and Wednesday 12:00 PM- 5:00 PM.

It was started about 30 years ago and offers a wide variety of products. Fresh fruits, vegetables and fresh cut flowers are staples, but you can also get organic beef, herbs, plants, soap, cheeses, breads and dog treats, and handmade crafts.

Number One Farmers' Market in Maryland
Kudos...Last year the Chestertown Farmers' Market in Kent County was voted the Numer One Farmers' Market in Maryland in the small market category for 2010.  The market finished seventh

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We know they will come back... but it is always a sigh of relief when Barbara and Kevin return from their annual 'Spring Break".  They returned a couple of weeks ago and have some new menu items to try out, and are introducing official "Burger Night" on Thursdays with a yummy Special Burger.  Their regular menu is also available.  Always fun to check out what's going on with their Website and Blog! Brooks Tavern.

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The creek has been frozen for awhile and we have enjoyed seeing the ducks and geese romping around.  But, it was a little more interesting this morning.  We looked out and there was a magnificent Eagle out there alone in the middle. He was quite content for awhile, just sitting there, checking things out.  Then he casually started walking over to the edge and disappeared into the marsh.  Guess it was time to get the day rolling.

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