Take a Quick Trip to Chestertown, Maryland

Chestertown is a short daytrip away from our beautiful Nauti or Knot getaway in Rock Hall

When you think of a vacation on the beautiful Chesapeake Bay, it’s hard to beat historic Rock Hall, Maryland, on the Eastern Shore. They call Rock Hall the “Pearl of the Chesapeake” for a reason.

The town sits at the crossroads of historical maritime shipping routes, adding rich character and unique flair to the marina and local shops. Anything Rock Hall lacks in amenities is made up for in its proximity to other prominent Chesapeake Bay towns.

Chestertown, Maryland is a short drive – or boat ride – from Rock Hall and offers the perfect day-trip opportunity. Established in 1706 as a colonial port city, Chestertown is a historic destination for art, shopping, dining, and history. A short 20-minute drive by land (or 14 nautical miles by boat), the best of the Eastern Shore is closer than you think.

The Historic Chester River

Boaters can explore the Historic Chester River with a trip from Rock Hall to Chestertown. The roughly 14 nautical mile route showcases the beauty of the Eastern Shore and retraces historical shipping routes. Chestertown was one of Maryland’s six Royal Ports of Entry for the English colony. Visiting boaters can dock their vessel at the Chestertown Marina for a small fee. The Marina also sells fuel and ice and has on-site bathrooms.

Boatless visitors can reserve a charter with the Chester River Packet Company. The company uses restored packet boats, originally used to transport mail, passengers, and freight down smaller rivers in the 19th century, to treat guests to a river tour and optional meal. Visit their website to learn more about the tour options, and reserve your tickets in advance, as these tours sell out quickly.

Chestertown Arts and Entertainment

Visitors can enjoy more than 200 years of history on display in Chestertown, Maryland. In their Arts & Entertainment district, shoppers and art lovers enjoy strolling along brick sidewalks in search of acclaimed RiverArts galleries, performing arts studios, and historical landmarks. The RiverArt district focuses on promoting regional artists and Chesapeake-centric artwork. 

If period art is more your style, take a step back in time with The Historical Society of Kent County. Their museum in Chestertown is known as the Bordley History Center. The building, formerly a family-operated men’s clothing store in the 19th and 20th centuries, was donated in 2014. Those interested in a tour can find it in the middle of the Chestertown Historic District, alongside other beautiful restored and maintained homes, businesses, and landscapes.

Flavors of the Chesapeake

A mainstay of Chestertown, though not quite as old as some traditions, is the Chestertown Farmers and Artisans’ Market. While the history of the market’s origin is the topic of much debate among residents–some believe there was a market established as early as 1762–many locals share stories of buying fresh seafood and produce off of wooden wagons in the 1940s and 50s. More recently, the market has been twice voted “Best in Maryland” by the American Farmland Trust.

In the heart of downtown Chestertown, the market is open Saturday mornings from 8 am until noon. Shoppers can find fresh from the farm produce, cheeses, and eggs alongside fresh-baked bread, pastries, and snacks. No Eastern Shore market is complete without fresh seafood–buy fresh to make later or indulge in a prepared meal from one of the many artisan vendors.

Rock Hall, Maryland offers the perfect launch point (pun intended) for your Eastern Shore vacation. Right on the Chesapeake Bay and a short drive from historic towns like Chestertown, the Nauti or Knot vacation home is the ideal setting for your next vacation. Whether you like to soak in the sun, explore historic towns, dine on fresh seafood, or shop until you drop, you can please everyone in Rock Hall.

When you’re ready to book your next family vacation in Rock Hall, look no further than our newly renovated ‘Nauti or Knot’ vacation home. ‘Nauti or Knot’ is a beautiful, elegant waterfront property with a private dock, small boat launch, 2nd-floor sundeck, game room, and much more – with space for 16 guests!

There’s still time to book ‘Nauti or Knot’ for 2022. Book now to reserve your Rock Hall family vacation today. And don’t forget to…

Stay Nauti!

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