Things to do & places to visit in Chestertown, Maryland, United States

With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.

Chestertown city in Maryland, United States. Timezone: America/New_York, current date and time: Saturday, May 11, 2024, 22:01.

Top things to do (27)

Top places to visit (30 attractions) view more »

5.0 Chester River Wine & Cheese Co. (27 reviews)
- Sophisticated choices and the most helpful manager ever!
Saturday: 10:00 AM - 5:00 PM Wine Bars

Located in historic Chestertown on the Maryland Eastern Shore, Chester River Wine & Cheese Co. is a specialty food market offering international and domestic wine, cut-to-order cheese, charcuterie and cured meats, as well as gourmet foods such as handmade jam, mustard, salts and sweets, pasta and specialty sauces, local beef, specialty sausage, olive oils and vinegars. Case discounts are available. See more..
5.0 Sultana Education Foundation (24 reviews)
- Sultana Public Paddles: A "must-do" when visiting the upper Chesapeake Bay area!
Nature & Wildlife Tours • Kayaking & Canoeing

Yesterday was another great day of kayaking in the upper Chesapeake Bay area with our fearless leaders, John and Chris, who are a wealth of information about the bay, John Smith and the Indian tribes he encountered in this area, and the plants, animals, and birds that call the Chesapeake Bay their home. Sultana's Public Paddles are leisurely 2.5 hour trips in some of the most beautiful and best kept secret areas of the bay. We have done all of their paddles time and again and always enjoy kayaking with them. What a great way to get some exercise and enjoy nature while meeting some of the nicest people you will ever meet! Don't forget your camera and binoculars if you have them! See more..
5.0 Twigs & Teacups (15 reviews)
- Twigs and Teacups has expanded!! Locals rejoice!!
Saturday: 10:00 AM - 5:00 PM Spent 1-2 hours Speciality & Gift Shops

Gifts and more On the Eastern Shore. See more..
5.0 Garfield Center for the Arts at the Prince Theatre (7 reviews)
- Sylvia by A.R.Gurney was excellent
Saturday: 11:00 AM - 2:00 PM Theaters

Since its inception in 2002, the Prince Theatre Foundation has enjoyed success in various community endeavors: - Producing top of the line theatrical and musical productions - Providing quality educational, enriching experiences in the arts for children and adults - Partnering with over a dozen community organizations Recognized and valued as a unique community center for the arts. See more..
5.0 Reflections Salon, Spa & Tanning Studio (4 reviews)
- Reflections is a truly relaxing spa!
Spent 1-2 hours Spas

Reflections is located just south of the Chester River Bridge on Route #213 in Chestertown, MD. We are a full service salon offering Hair Services, Manicure, Pedicures,Waxing, Award Winning Facials, Exquisite Massage,Sugar Body Scrubs, Sauna, Red Light Therapy and Tanning. See more..
5.0 Art on High (3 reviews)
- Talent is extraordinary
Saturday: 12:00 PM - 6:00 PM Spent < 1 hour Art Galleries

The Gallery at Rock Hall is a Contemporary and Modern collection of artists from near and far. We have a small collector's corner for those who search for the obscure yet valuable. Our eclectic collection is hand picked and curated with passion and a love for color and individuality. We welcome you to pay us a visit and enjoy paintings, photography, jewelry and sculpture. See more..
5.0 Create (2 reviews)
- Beautiful Art in a Small Town
Spent < 1 hour Speciality & Gift Shops • Art Galleries
Create.art.craft.design is a gallery of hand-made American Craft, representing some of the top Art/Craftspeople in their fields, including the partners. In addition to it's outstanding collection of pottery, glass, fiber, metal and wood, Create has one of the finest and most unique jewelry collections in the region. The partners are also knowledgeable and helpful about the area. See more..
5.0 Elbe Body (1 review)
- Relax Those Muscles
Spent 1-2 hours Spas
Linda Moyer, massage therapist and owner of Elbe Body, provides a soothing atmosphere to enhance the massage experience. My tired muscles are gently massaged and kneaded until I am totally relaxed. She is attentive to every detail, from calming oil to the comfortable massage table, to her experienced, gifted hands with which she massages you. If you are looking to rejuvenate your aching body or to completely relax, Elbe Body comes highly recommended by this seasoned (12 years) massage client. See more..
5.0 The Back 50 (1 review)
- Best Bar in Chestertown
Saturday: 3:00 PM - 1:00 AM Spent More than 3 hours Bars & Clubs

This is the best bar I've ever been to. People know you. Come on Sundays during football season--heck, come any time of year--it's like a tailgate. Remember the show Cheers? You want to go where everybody knows your name. Hidden gem. Awesome place. Awesome times. See more..
5.0 Emmanuel Chester Parish (1 review)
- The Holy Grail
Religious Sites
Chestertown, Maryland (along with Rock Hall) are two special places in Kent County (on Marylands Eastern Shore....along the Chesapeake Bay. Chestertown was originally designated by the British as the "Port of Call" for all goods being shipped to England (and return) from the Eastern Shore. The little town on the Chester River (RT#213) saw itsself prosper and grow in the late 16 and 1700's. With this growth came the English system of government and religion (Church of England) which controlled the Parish. Emmanuel Church was the center of the Parish...The Parish dominated all schools, governmental activitties and the way of life under the English. To be someone in the Parish was to be a member of Emmanuel Church and others in the County. This system lasted until the end of the Revolutionary War when the English were removed, and we became the USA. It was at Emmanuel, before the war ended, that Dr Wm Smith created a seperate Anglican branch of the Church of England: The Protestant Episcopal Church. One could go on, but to visit Chestertown is not only Emmanuel, but The Histotric Pier, The Customs Houses, and the amazing "Philadelphia Plan" created by Benjamin Franklin. You need to see Chestertown and Rock Hall to really get a view of The Eastern Shore...well worth the visit: History, Crabs, Oysters, Architecture, and more. See more..
4.5 Chester River Packet Company (72 reviews)
- Great way to spend a Sunday afternoon
Boat Tours • Sightseeing Tours

Excellent way to spend a Sunday afternoon! Boat is very clean and staff and crew couldn’t have been nicer. Includes a nice narrative by a well-informed Captain. (I had NO idea the Chestertown area had such an interesting history.) Lunch was excellent as well! Worth every Penny of the $45 p/couple charge. Definitely looking forward to a repeat visit! See more..
4.5 Book Plate (32 reviews)
- A Must Visit for All Book Lovers
Saturday: 10:00 AM - 5:00 PM Speciality & Gift Shops

Book lovers can spend hours in this wonderful used bookstore. Very well curated with a wealth of books in all categories. Friendly and helpful staff, including Tom the owner. Don't miss this gem if you are in Chestertown. See more..
4.5 MassoniArt Gallery (28 reviews)
- Get your coffe downstairs at Evergrain and go upstairs to see Carla
Saturday: 11:00 AM - 3:00 PM Art Galleries • Points of Interest & Landmarks

Respected by artists & collectors throughout the Mid-Atlantic region for over 30 years. For over 30 years, the Carla Massoni Gallery has worked in collaboration with architects, developers, interior design firms, art consultants, and non-profit organizations to bring art to the workplace. We have been honored to work with the US State Department’s Art in Embassies Program placing our artists work in American embassies throughout the world. We have placed works of art in SoHo lofts, New Jersey pharmaceutical companies, Delaware corporations, Baltimore non-profits, and Washington, DC law firms and associations. We provide a conduit for artists to interact with the business community by arranging opportunities for their work to appear in journals, newsletters and national publications. See more..
4.5 Historical Society of Kent County (18 reviews)
- I live here & LOVE this place
Saturday: 10:00 AM - 3:00 PM Spent < 1 hour Speciality Museums

The Historical Society of Kent County, Maryland, is a non-profit organization dedicated to the collection and preservation of artifacts, documents, and information that aid in the interpretation of all aspects of Kent County’s history. The Society shares this information through its research library, museum space, programs, publications and website in order to foster a knowledge and understanding of the shared heritage of the community. The Society supports and encourages the preservation of historic buildings and sites throughout Kent County. See more..
4.5 Bee Crafty Antiques & Collectibles (3 reviews)
- Super cute store
Spent < 1 hour Speciality & Gift Shops • Antique Shops

You will find items for every occasion. Painted furniture is my specialty along with custom made signs. This store has various hand made local and made in the USA items. If you are looking for that different and unique gift you will find it here. I also carry Infused Honey Products for sale. Please stop in you will be amazed!! See more..
4.5 Poor Richards of Chestertown (3 reviews)
- Great variety!
Spent < 1 hour Speciality & Gift Shops • Antique Shops
Nothing Over A Million Dollars! An eclectic mix of fun and games, fashion accessories and jewelry, children's toys and activity kits, and great things for kitchen, home and entertaining. A great collection of coffee table books by Assouline Publishing House. See more..
4.0 River Arts Chestertown (19 reviews)
- Replaced by Chester River Artworks
Lessons & Workshops

RiverArts Mission: To engage our community in the creation, appreciation, and support of the arts through education, events, and exhibitions. RiverArts Vision: To inspire and foster creativity as a positive and sustainable force that enriches our community and establishes the region as a premier arts destination. See more..
4.0 Kent County Visitors Center (13 reviews)
- A Worthwhile First Stop for Visitors
Spent < 1 hour Visitor Centers
This was our first stop, as we were first-time visitors to Chestertown, as we explore potential places to retire. The Welcome center has plenty of parking, it is clean and welcoming. The attendant was very knowledgeable, friendly, and helpful. There are many free brochures, all very helpful. Just what we needed. Noticed bathrooms on the way out, but did not check them out. See more..
4.0 jellyfish joel's (12 reviews)
- Great climax to my day
Bars & Clubs

Jellyfish Joel's Review Great place to spend the day. Picnic tables galore. Food Truck right on the beach for tasty food. Exciting up close view of yachts passing through the Fairlee Creek inlet. Free golf cart transportation. HC Jones See more..
4.0 Fountain Park (2 reviews)
- Center of Town
Parks

Close to the must see points within town. Not to busy. Good antique shopping opportunity in the neighborhood. See more..
4.0 Chesapeake Farms (1 review)
- A Natural Setting
Nature & Wildlife Areas
Chesapeake Farms is a 3300 acre agricultural and wildlife management research and demonstration and education area. It was originally a hunting preserve for employees of the Du Pont Company. There is a self guided driving tour only with 14 stops thru out the property and is very informative. You can pick up a leaflet at the beginning and read as you go. We saw waterfowl, turtles, snakes and even muskrat along our journey. Due to the road conditions, I would avoid visiting after a heavy rainfall. See more..
Mike Dunlap (0 review)
Multi-day Tours • Sports Camps & Clinics • Adrenaline & Extreme Tours • Fishing Charters & Tours • Hiking & Camping Tours • Private Tours • Nature & Wildlife Tours • Day Trips

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Body Mechanics Massage Studio (0 review)
Spas

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Sultana Education Foundation (0 review)
Saturday: Historical & Heritage Tours • Boat Tours • Nature & Wildlife Tours • Kayaking & Canoeing

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Jelly Fish Joels (0 review)
Bars & Clubs

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Fit Flock, LLC (0 review)
Spent < 1 hour Lessons & Workshops

Fit Flock is a fitness studio offering personal training and health coaching sessions, in person and virtually. It is by appointment only. See more..
Safe Harbor Great Oak Landing (0 review)
Marinas
Safe Harbor Great oak Landing is an adult and kid friendly resort that you can come to by boat or car Here at the marina you can either stay on your boat or in out hotel! We have a pool, restaurant, volley ball court and even a beach bar! Boat reservations are a seperate fee and are made through DOCKWA. See more..
The Finishing Touch (0 review)
Spent < 1 hour Speciality & Gift Shops
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The Seed House (0 review)
Sports Camps & Clinics

The Seed House is a Yoga Studio, Cafe, Coffee Bar, and Wellness Center offering personalized holistic and complementary services such as massage, acupuncture, physical therapy, reiki, reflexology and nutrition support. Our cafe features local, organic ingredients cooked from scratch with offerings to please omnivores to vegans. Stumptown coffee. House made Kombucha and cold pressed juices. See more..
Chestertown Electric (0 review)
Spent < 1 hour Antique Shops
Early electricity in the home - lamps, telephones, ceiling & desk phones, wall outlets/plugs/switches, heaters, motors, and other curios. Touch and use the items and learn how they work, Most items are for sale. Restoration services and lamp rewiring available. Specializing in antique fans. See more..