Chestertown Fountain Park
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Top 10 Things to See and Do in Chestertown

Founded in 1706,  Chestertown is a historic college town along the banks of the Chester River on Maryland's Eastern Shore. The brick sidewalks lined with shops, restaurants and inns welcome visitors to meander and browse. A visit to Chestertown's Historic District to admire the fine colonial residences is a must!.

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Chestertown A&E District

1 Arts

Explore Chestertown's Main Street and Arts & Entertainment District and discover a town in which arts and cultural thrive.
Check out this map of galleries, restaurants and shops.

reenactors on ship Photo By: Chestertown Tea Party Festival

2 Annual Festivals and Events

Experience Chestertown like a local by attending one of the many unique annual events. During Memorial Day weekend there is the annual Chestertown Tea Party Festival and don't miss the Pirates and Wenches Fantasy Weekend in August - but no matter what time of year you visit, you can count on an entertaining event or festival.
More info....

Garfield Center Marquis in Chestertown Photo By: Clark Vandergrift

3 The Garfield Center for the Arts at the Prince Theatre

The Garfield shakes up the cultural life of Chestertown with great programming that nurtures and celebrates arts and artists - essential elements of life in Chestertown.
More info...

dog at Crow Vinyard Photo By: Clark Vandergrift

4 Dog Friendly

With its very own dog park, Chestertown is the perfect place for your furry friend to wag his tail and enjoy the refreshing breeze of this waterside retreat. The Kent County area has plenty of pet-friendly businesses for pets to explore as well.
More info....

Antique books

5 History

Serving as Kent County's seat of government since 1706, Chestertown has been a Royal Point of Entry, the scene of its own Revolutionary Tea Party in 1774, and the hub of a bustling agricultural and seafood region. The Historical Society of Kent County is a treasure trove of history and offers a great self-guided walking tour you can access via your smartphone.


More about Historical Society of Kent County
Visit Website


Type:
Attraction


Location:
301 High St
Chestertown, MD 21620
410-778-3499


Washington College Photo By: Washington College

6 Washington College

Founded in 1782, Washington College was the first college chartered in the sovereign United States of America. General George Washington lent his name, donated 50 guineas to the founding and served on its first Board. The mission back then was to cultivate responsible citizen-leaders. Nowadays, the focus is on giving students the chance to succeed on their own terms.
More info...

Tall Ships Photo By: Town of Chestertown

7 Schooner Sultana

On board the Sultana,  people connect to the Chesapeake Bay’s history, ecology, and culture, and become inspired to be a part of  preserving and restoring America’s largest estuary.

Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast. 


More about Sultana Education Foundation
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Type:
Attraction


Location:
200 S. Cross St
Chestertown, MD 21620
410-778-5954


vintage finds Photo By: Crumpton's Auction

8 Crumpton Auction

Crumpton's is a third-generation auction company established in 1961 by Norman Dixon where everythng moves at a fast pace. With seven auctioneers on staff  it is not unusual for Crumpton's to conduct three to four auctions simultaneously resulting an average of 200 items sold per hour or 3,000 to 6,000 lots a week. You  never know what you may discover at Crumpton's whirlwind of vintage treasures.

  


More about Dixion's Crumpton Auction
Visit Website


Type:
Attraction


Location:
2017 Dudley Corners Rd
Crumpton, MD 21628
410-928-3006


Maryland crabs and corn

9 Eat & Drink

Chestertown  is a magnet for traveling foodies. Known for its wealth of Chesapeake Bay cusine, Chestertown is located on the Upper Eastern Shore Section of the Maryland Crab & Oyster Trail .Visiting the Chestertown Farmers and Artisans Market (opens at 8am every Saturday, year-round) is a great way to aquaint yourself with the local farmers and artisans. One of the newer additions to Chestertown's food repertoire is Figg's Ordinary, an entirely gluten-free cafe. For something a little stronger head to  Bad Alfred’s, a brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas.
Check out all of the fantastic dining options in and around Chestertown here.

Red brick Inn Photo By: The White Swan Tavern, Colonial Inn

10 Charming Inns and B&Bs

When you visit Chestertown you'll want to relax and slow the pace by staying the night at one of Chestertown's charming B&B's or Inns. More info...

Chestertown Photos & Videos

Chestertown_Historic_District_Marker-CV-1800px.jpg
Chestertown Historic District Marker
Photo By: Clark Vandergrift
Chestertown_Garfield_Center_Marquis-CV-750px.jpg
Garfield Center Marquis in Chestertown
Photo By: Clark Vandergrift
Chestertown_Selfie_Couple-CV-1800px.jpg
couple taking selfie
Photo By: Clark Vandergrift
Kent-Dog_Crow_Vineyard-CV-1800px.jpg
dog at Crow Vinyard
Photo By: Clark Vandergrift
Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival
Tall Ships
Photo By: Town of Chestertown
Historic_Home_Chestertown-ClarkV-1800px.jpg
Historic Home
Photo By: Clark Vandergrift

Chestertown

Trip Ideas

Chestertown Fountain Park
Top 10 Things to See and Do in Chestertown

Stroll historic tree-lined streets, and explore the natural beauty of the Chester River

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Antique Car
Places to Stay and Things to do in Chestertown

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Places to Stay and Things to do in Chestertown

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