Experience Water Sports Around Chestertown MD

An array of different bodies of water practically surrounds Brampton Inn. From the Eastern Shore of the Chesapeake Bay to the Atlantic Ocean, the Chester River, state parks, and more, it can take time to know where to begin your outdoor water adventure. Broken down into several categories, take time to check out the water sports around Chestertown, MD, to find the perfect summer adventure for you!

Kayaking & Paddleboarding

Enjoy the summer sun with the leisurely water sports of kayaking or paddleboarding. As summer sweeps through the Eastern Shore, kayaking and paddleboarding are two of the best ways to take in the stunning flora and fauna around Brampton Inn from the water.

Canoeing & Birding

Speaking of the fauna you can see from the water, let’s talk about birds! Birding is in full swing this summer as folks begin taking to the water to enjoy the sunny riparian ecosystems. Great Blue Heron, Bald Eagle, Bank Swallow, Yellow Warbler, Mute Swans, and more! Canoeing is a great — and super romantic — way to leisurely coast through the water and peek at these birds in their natural habitat.

Sailing Adventure

Sailing is one of the most popular summer pastimes on Maryland’s Eastern Shore. On the famous Chester River or the bay beyond, a public or private sailing adventure is (in our opinion) a bucket list experience. There is just something so special about being on the water with the wind blowing through your hair.

For a sailing adventure that is pre-planned, stress-free, and incredibly romantic, we put together the ultimate Sailing Package just for the two of you. Check it out!

Gone Fishin’

Indulge in the ultimate summer water sport with a day of fishing. Fish for local specimens such as red drum, largemouth and striped bass, white perch, and an array of catfish. Whether you opt for a leisurely stand-up paddleboard (SUP) experience, a rented boat, or a guided tour, we know that you will find some of our area’s best “hidden gem” locations on the lakes, the Chester River, and other local wetlands.

Local Water Adventure

  • Sultana Public Paddles — Explore lakes and wetlands at varying locations along the Eastern Shore with a public paddling adventure! This unique guided kayaking experience is the perfect way to get outside and take in all the sights this summer.
  • Barefoot Adventures — Looking for the place that does it all? Check out Barefoot Adventures with Capt. Mike Dunlap to explore outdoor excursion options such as fishing charters, SCUBA instruction, sailing, surfing, and more! Plus, this company allows you to experience no motor and just the sounds of nature with a guided SUP fishing adventure.
  • Chestertown River Packet Company — enjoy public cruises along the scenic and historic Chester River. This particular company offers an array of relaxing dinner cruises for occasions big and small, or just because, all summer long!
  • Sultana Public Sails — These two-hour, hands-on sailing experiences are an affordable and fun way to create memories you will never forget! Experience helping raise the sails, steer the sailboat, and even take a peek at authentic crew quarters below deck.

Whether it be by river, sea, or other, we hope that you found the summer water adventure that best suits you. After experiencing water sports around Chestertown, MD, end the night at our boutique hotel. You can step into a refreshing shower or soak in a spa tub, sip on a glass of wine by the fire, and then rest in a cozy bed. Let the relaxing ambiance of one of our private cottages be the cherry on top of your day under the Maryland sun.

Explore more of our Eastern Shore with a day trip to St. Michaels, MD!

Published July 2023

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