5 Top Things to Do in Summer in Chestertown MD

A Chestertown summer is right around the corner! As nature awakens and we start to spend more time in the sun, we can’t help but want to share our little slice of paradise with you.


With so much to do and see, planning the perfect summer itinerary can be overwhelming and difficult. That is why we have compiled a comprehensive list of some of the top things to do in summer in Chestertown, MD. Everything from outdoor recreation, food and drinks, arts and culture, shopping, and places to stay is listed to give you some starting points for your sweet summertime getaway. Enjoy!

1. Enjoy Outdoor Recreation

It is time to get outside and enjoy the blue skies and warm weather of Maryland’s eastern shore. Here are some of our favorite activities to get you started planning your Chestertown, MD itinerary!

  • Blue Crab Sailing — Let the wind do the work as you skim along the deep blue waters off Sharp St. Pier in Rock Hall, MD. This is one of the most popular summer activities in the area, so make sure you book your reservation soon! Experience Chesapeake Bay from the water while enjoying a relaxing and visually stunning sail.
  • Eastern Neck National Wildlife Refuge — Looking to stay on land but still see the natural sights of the eastern shore? This wildlife refuge hosts over 240 bird species and is designated an Important Bird Area by the Audubon Society. Located on its very own 2,285-acre island, it offers the best views of the land and sea. With beautiful hiking trails and lookout areas, this is one of the best outdoor recreation sites around, and we are lucky to have it right in our backyard.

2. Experience Arts & Culture

Art and culture are a huge deal here in the Eastern United States. Did you know we have some famous museums and art centers surrounding us? There are so many good ones, but we recommend these to you for your next summer getaway.

  • Massoni Art Center — This renowned art center is a beautiful collection of pieces from around the world. They feature unique pieces honored and used by the US State Department’s Art in Embassies Program. With two locations in Chestertown, this open gallery is a must-see.
  • Garfield Center for the Arts — Open mic nights, live theatre, comedies, musicals, and more. The Garfield Center is the perfect place for a night on the town or even just a lovely cultural experience to explore on a warm summer day. 
  • The Mainstay — Nicknamed the “Home of Musical Magic,” The Mainstay’s non-profit live music venue is sure to be an experience you will remember forever. Their summer shows are beginning now — don’t miss out!
  • Raimond Cultural Center — Say hello to the newest art and culture experience in Chestertown! After a four-year renovation, it is finally time to open the doors of this historic and culturally significant center. The main gallery and space for live events is open to the public, where they will be hosting poetry readings, seminars, and more all summer long.

3. Explore our Shops

On vacation, shopping around the area like a local is always fun. Who knows what treasure you will find to take home as a token of a beautiful getaway? We have provided some must-shop-stops that are perfect for your next visit. 


  • Twigs & Teacups — One of the most charming, small-town stores we can imagine! This whimsical store is a hidden gem. Check out Twigs & Teacups for a wide range of locally produced products, gifts, and more.
  • The Hickory Stick — A unique boutique that carries a little bit of everything! This cute little store has a nautical feel and offers some big-name brands mixed with local crafts. These hand-picked items rotate in and out of the store, so you can really pick up a one-of-a-kind gift. 
  • Houston’s Dockside Emporium — This emporium is THE place to go for men’s and women’s apparel in downtown Chestertown, MD. Clothing, jewelry, towels, and other treasures are just waiting to be picked up!

4. Indulge in Some Delicacies

Summertime, delicious food, and a good drink in hand are everything we could ask for! Take time to relax and catch up with a loved one over a tasty dinner. Here are some of our favorite summer-season restaurants you can’t miss on your next trip. 

  • The Kitchen at the Imperial — This spot offers exceptional food. So exceptional, in fact, that we partner with them for our wine-pairing dinners for guests! It is hard to beat their fresh seafood and exquisite ambiance. Definitely worth visiting!
  • Blue Heron Oyster House — After you return from your Blue Crab Sailing adventure in Rock Hall, stop by this restaurant. They offer fresh, seasonally caught seafood dishes that are absolutely divine. Our mouths are watering just thinking about it.
  • The Retriever Bar & Oysters — This is not your usual fare. They offer some of the finest Atlantic oysters you can find in the area! Plus, check out the adjacent Decoy Bottle Shop for a fantastic beer, wine, and spirits selection. Life is short — try something new! 

5. Relax at the Best Place to Stay

The Brampton Bed & Breakfast Inn — Of course! Comfortable, luxurious, and oh so charming…we are so proud to welcome you to our Inn. The rooms are enchanting, the grounds are captivating and in full bloom, and the freshly cooked food is delicious! We may be biased, but we firmly believe that a unique and personalized stay at our Inn is something you will remember for years to come.


There you have it! We hope you enjoyed reading through our list of top things to do in summer in Chestertown, MD, as much as we enjoyed making it. These Eastern Maryland treasures are full of places and people with a very special place in our hearts. Of course, we would love to host your stay at Brampton as you take time to get away this summer and experience something new.


Published May 2023

Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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