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Shop for glass ornaments, jewelry and more during the RiverArts Studio Tour Oct. 19-20 and Oct. 26-27.

Summer’s gone, but the party isn’t over in Kent County, Md.

A getaway to this scenic Chesapeake Bay locality on Maryland’s Upper Eastern Shore — a two-hour drive from Washington, D.C. — offers plenty of options through the end of the year.

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The Chestertown, Md., Farmers and Artisans Market operates year round.

Think the time is past for browsing a farmers market? Not for the popular Chestertown Farmers and Artisans Market, which happens year round on Saturdays at Fountain Park at High and Cross streets.

“It’s a great place to hang out,” said Sabine Harvey, who oversees the market. “It’s right smack downtown.”

Shop for locally produced seasonal fruits and vegetables, seafood, baked goods, cheese, meats, wine and flowers.

“There’s every single produce you can imagine” through October, Harvey said, and cold-weather crops after that.

Artisans sell unique handcrafted items, such as paintings, pottery, jewelry, wooden items, clothing and more. Nonprofit organizations are on hand, and there are kids’ activities and sometimes live music.

Harvey suggests grabbing a coffee, sitting next to the fountain and indulging in some people (and dog) watching.


The Chestertown Jazz Festival is a big hit in the fall in Kent County, Md. This year's festival is Sept. 12-16.

Stroll the brick sidewalks of Chestertown to enjoy boutiques, antique stores, bookstores, art galleries, gift shops, bakeries, locally owned restaurants, wine and cheese shops, and a distillery. Shops stay open later on first Fridays of the month.

The town that once welcomed George Washington and Thomas Jefferson is filled with architecturally interesting 18th- and 19th-century homes, as well as Washington College, founded in 1782.

Fun on the water

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The Sultana Downrigging Festival Nov. 1-3 is one of Kent County's most popular festivals.

For a relaxing time, board the Chester River Packet for two-hour cruises Thursday and Friday evenings; Saturday afternoons; and Sunday brunch through New Year’s Day. The replica 1920s touring yacht operates from the foot of High Street in Chestertown. Sit in the boat’s air-conditioned salon or on open-air decks. Reservations are suggested.

“I’m probably the most handsome riverboat captain in all of Chestertown,” joked Greg Kimmel. “Wait — I’m the only one”!

The personable Kimmel delivers the commentary “with a lot of poetic license” as the boat passes scenic undeveloped land, historical farms and Georgian-style mansions. Cruises go as far as Quaker Neck Landing on the Chester River and sometimes into the Corsica River and Langford Creek.

“It’s a step back in time,” he said.

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The Chester River Packet offers scenic cruises through New Year's Day.

Panoramic views, fall foliage, and deer and waterfowl sightings add to the pleasure, and you can experience the sunset from two different angles. (“Two for the price of one,” Kimmel quips.)

The catered, high-end buffet with a cash bar is a big draw. On Saturdays, bring your own picnic lunch.

Passengers rave about the cruises, with comments like “breathtaking” and “the food is off the charts,” said Kimmel.

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The Chester River Packet offers scenic cruises through New Year's Day.

The River Packet sponsors the spectacular fireworks display during one of the county’s most popular festivals, the Nov. 1-3 Sultana Downrigging Weekend. The Packet drops anchor and becomes a floating restaurant that weekend, though it offers special cruises to see the illuminated ships at night.

The Sultana, a replica of a 1768 schooner, and a fleet of other tall ships, converge at the Chestertown marina for tours and sails. A waterfront village is set up featuring bluegrass music, author lectures, children’s activities, food and drink.

Blue crabs and festivals

Visitors enjoy exploring Kent County’s small towns, picturesque harbors, farms, museums, dining and recreational opportunities and festivals.

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The Harry Potter Festival in Chestertown, Md., will cast a spell Oct. 4-5.

Upcoming events include Chestertown Jazz Festival (Sept. 12-14); Harry Potter Festival (Oct. 4-5); RiverArts Studio Tour (Oct. 19-20 and Oct. 26-27); and Dickens of a Christmas (Dec. 7). Visit for a complete calendar. 

Garfield Center for the Arts in Chestertown and The Mainstay in Rock Hill offer theater productions and concerts.

Chesapeake Bay blue crabs and Maryland crab cakes attract seafood lovers. Favorite spots to dine include Waterman’s Crab House, often rated the “Best of the Bay,” and Ford’s Seafood, both in Rock Hall; The Kitchen at the Imperial in Chestertown and the Fish Whistle in Georgetown. For a bushel of crabs, visit Clark’s Seafood in Chestertown or Chester River Seafood in Rock Hall.


Jerry Brown and his monkey Django perform magic shows and stroll the streets in Chestertown during the Dickens of a Christmas festival on Dec. 7.

The weather is still good for boating, paddling canoes and kayaks, fishing, hiking, bicycling and birding.

And if you just want to sit back and do nothing, there are bed-and-breakfasts, historic inns, rental properties and campgrounds to accommodate you. Many are pet-friendly.

For more information:

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