Chestertown, Maryland, is a charming small town filled with history, creativity, and outdoor fun. Located on the beautiful Chester River, it offers something for everyone, from art lovers to nature enthusiasts. Whether you want to learn about the town’s rich past or enjoy a day by the water, Chestertown has plenty to offer.
Let us explore some of the best activities and sites to enjoy in this delightful town. From local art galleries to picturesque parks, you’ll find plenty of ways to make lasting memories in Chestertown. Get ready to experience the unique charm and culture that make this town special.
Things to Do in Chestertown MD
1. Visit MassoniArt Gallery
MassoniArt Gallery is a vibrant hub in Chestertown, showcasing contemporary art. It features both local and regional artists. You can explore rotating exhibitions that change frequently, giving each visit a fresh experience.
Upon entering, you will find a dynamic range of artwork, from paintings to sculptures. The gallery aims to highlight unique artistic expressions. The friendly staff is always ready to share insights about the pieces on display.
Visiting MassoniArt is not just about viewing art; it’s about engaging with the community. The gallery often hosts events and openings. These events provide an excellent opportunity to meet artists and fellow art lovers.
After enjoying the art, take a moment to appreciate the gallery’s location. It’s set in the heart of Chestertown, making it easily accessible. You can stroll around the historic streets or enjoy a coffee in a nearby café afterward.
A visit to MassoniArt Gallery is truly enriching. It promises to inspire and leave you with a sense of connection to the local art scene.
Address: 203 High St, Chestertown, MD 21620.
2. Catch a Show at the Garfield Center for the Arts
The Garfield Center for the Arts is a true gem for theater lovers. Located in a beautifully restored historic building, it offers a range of live performances. You can find everything from plays to concerts that cater to various tastes.
Each show promises to deliver high-quality entertainment. The theater’s intimate setting enhances the experience, making you feel connected to the performance. Check their schedule for upcoming events and book your tickets in advance.
The theater also runs community programs. These include workshops and classes that encourage local talent. It’s a great way to engage with the arts if you have a passion for performance.
Enjoy a night out after the show by exploring nearby dining options. There are several charming restaurants where you can grab dinner. Many offer a cozy atmosphere, perfect for discussing the show you just attended.
A visit to the Garfield Center makes for a delightful night. Art and community come together here, creating lasting memories.
Address: 210 High St, Chestertown, MD 21620.
3. Explore the Historical Society of Kent County
The Historical Society of Kent County offers a fascinating look into the past. This museum hosts exhibits and archives that tell the story of Kent County. You’ll find artifacts that reflect the local culture and history.
Walking through the exhibits, you will discover the significant events that shaped the region. The knowledgeable staff can provide insights and answer any questions you might have. They are passionate about sharing Kent County’s story with visitors.
In addition to the exhibits, the society offers programs and events. These often focus on local history and encourage community engagement. Their events provide a great opportunity to learn more about the rich heritage of the area.
The museum’s location is also a plus. It’s situated in a quaint part of Chestertown, perfect for a leisurely visit. After exploring the museum, take a stroll through the charming streets nearby.
Visiting the Historical Society is both educational and enjoyable. It’s a great way to connect with the history of Kent County.
Address: 210 High St, Chestertown, MD 21620.
4. Relax at Safe Harbor Great Oak Landing
Safe Harbor Great Oak Landing is a perfect escape for nature lovers. This marina resort offers stunning waterfront views and various outdoor activities. You can relax by the water, go boating, or indulge in fishing.
The on-site restaurant serves delicious meals that are hard to resist. Enjoy dining while overlooking the beautiful waters of the Chester River. It’s a lovely spot for a meal after a day of fun in the sun.
The resort atmosphere is friendly and inviting. Families and friends gather here to enjoy the natural surroundings. You can also participate in community events that take place throughout the year.
For those looking to stay longer, they offer comfortable lodging options. It’s a great way to immerse yourself in the beauty of the area. Wake up to serene views and the sounds of nature.
Safe Harbor is more than just a marina; it’s an experience. You’ll leave feeling rejuvenated and connected to the picturesque outdoors.
Address: 24350 Great Oak Landing Rd, Betterton, MD 21610.
5. Stop by the Kent County Visitors Center
The Kent County Visitors Center is your gateway to discovering Chestertown. Friendly staff are ready to provide maps, guides, and local insights. Here, you can learn about all the attractions available to you.
The center also features local art and crafts that encapsulate Kent County’s spirit. It’s a good spot to pick up souvenirs to remember your visit. You may even find some unique items to take home.
In addition to information, the center often hosts community events. Check their calendar for upcoming workshops and festivals. Engaging with local events enhances your understanding of the area.
Accessible and welcoming, the Visitors Center is a must-see at the start of your trip. Get recommendations for dining and attractions tailored to your interests.
Stopping by here will enrich your visit. You’ll gain valuable insights to make the most of your time in Chestertown.
Address: 400 High St, Chestertown, MD 21620.
6. Stroll along the Chestertown Sketch Club
The Chestertown Sketch Club is a delightful gathering spot for art enthusiasts. This community-based organization allows artists to come together and create. Visitors are encouraged to join, whether you’re a beginner or an experienced artist.
Participating in sketching sessions is a wonderful way to enjoy the scenery. The club often meets in picturesque locations around Chestertown. You’ll get inspired by the historic architecture and natural beauty.
Even if you don’t want to draw, observing the artists at work is enjoyable. The atmosphere is always friendly and encouraging. You may also meet fellow art lovers who can share tips and techniques.
The club’s events are open to the public, so feel free to drop by. It’s a fantastic way to connect with creativity while exploring the town.
Strolling through the Sketch Club makes for a memorable afternoon. You may leave with new skills and improved appreciation for art.
Address: 510 Washington Ave, Chestertown, MD 21620.
7. Explore Betterton Beach
Just a short drive from Chestertown, Betterton Beach is a hidden gem. Its sandy shores are perfect for a relaxing day by the water. You can swim, sunbathe, or enjoy a picnic with your loved ones.
The beach is family-friendly and offers facilities such as restrooms and picnic spots. You can bring your beach gear and make a day of it. The gentle waves make it a safe spot for children to play.
As you walk along the shore, you can collect shells or simply enjoy the sunrise. The views are stunning, providing a serene escape from daily life.
Nearby, you’ll find small shops and cafes where you can grab a bite after your beach time. These local spots add to the charm of visiting Betterton Beach.
Betterton Beach is a perfect location for a fun and relaxing day. Its peaceful atmosphere and lovely scenery are bound to lift your spirits.
Address: Betterton Rd, Betterton, MD 21610.
8. Tour the Historical Chestertown Courthouse
The Historical Chestertown Courthouse is a must-visit for history enthusiasts. This stunning building dates back to the 18th century and is an architectural gem. It stands as a witness to many important events in the region’s history.
As you tour the courthouse, you’ll learn about its role in the local justice system. The Courthouse often features exhibits that delve into Kent County’s judicial history. You can also explore interesting artifacts from the past.
The guided tours are informative and engaging. Knowledgeable guides share fascinating stories that bring the courthouse to life. It’s an excellent way to immerse yourself in the local culture.
The courthouse is located in the vibrant heart of Chestertown, making it easier to explore nearby shops and restaurants after your visit. The area is enriched with historical significance.
Visiting the courthouse offers a glimpse into the past. It’s a powerful reminder of the town’s heritage and its commitment to preserving history.
Address: 100 N Cross St, Chestertown, MD 21620.
9. Visit the Chester River Seafood
Chester River Seafood is a fantastic spot for seafood lovers. This local eatery serves fresh catches from the water. With delicious offerings, it is known for its casual dining environment.
Order up their famous crab cakes or enjoy a seafood platter. Each bite reflects the quality and freshness of the ingredients used. The riverside location adds a delightful touch to your dining experience.
In addition to dine-in options, they offer seafood market services. This allows you to take home fresh seafood to prepare at your own convenience. You’ll find various fish and shellfish ready for you to savor.
The staff is friendly and knowledgeable. They can recommend the best dishes depending on your taste preferences. Dining here is a delicious and relaxing experience.
A visit to Chester River Seafood is more than just a meal; it’s a taste of the local flavors. It’s a must for anyone exploring the Chesapeake region.
Address: 537 Quaker Neck Rd, Chestertown, MD 21620.
10. Take a guided kayak tour of the Chester River
Experience the beauty of the Chester River with guided kayak tours. These tours offer a unique way to explore local ecology and appreciate nature. Paddling through serene waters allows you to connect with the environment.
Guides are knowledgeable about the area and will share interesting facts and stories. You learn about the wildlife and plants that make the river special. It’s an educational and enjoyable adventure.
No prior kayaking experience is necessary. All equipment is provided, making it easy for anyone to join. The tours cater to all skill levels, ensuring everyone feels comfortable.
The peacefulness of gliding through the water enhances the experience. You may even spot birds or other wildlife along the banks. Bring your camera to capture the beautiful vistas.
Kayaking the Chester River is a memorable outing. It’s a fun, healthy, and engaging way to appreciate the outdoors.
Address: 5 Maryland Ave, Chestertown, MD 21620.
11. Check out the annual Chestertown Tea Party Festival
The Chestertown Tea Party Festival is a lively celebration of local history. Held annually, it commemorates the town’s role in the American Revolution. The festival features various events, food stalls, and entertainment for all ages.
Guests can enjoy live music performances and theatrical reenactments. These performances bring history to life and engage attendees in a fun way. Children can participate in games and activities designed just for them.
The festival is also an excellent opportunity to sample local cuisines. Many local vendors set up booths, offering everything from delicious treats to artisanal crafts. You can find unique souvenirs to take home, supporting local artisans.
Bring your family and friends for a day of fun and learning. The atmosphere is friendly and festive, ensuring a delightful experience for everyone involved.
Attending the Chestertown Tea Party Festival is not just about history; it’s about community and celebration. Join in the festivities and feel the town’s vibrant spirit.
Address: Chestertown, MD 21620.
12. Discover the ‘Custom House’ on High Street
The ‘Custom House’ on High Street is a charming maritime museum. It showcases the rich history of shipping trade in Chestertown. Visiting offers a unique insight into the maritime culture that shaped the region.
Inside, you will find various exhibits detailing the local shipping industry. You’ll learn about the significance of the waterways and the impact on the local economy. The displays are informative and help visitors understand the stern, yet engaging past.
Guided tours are available, making the experience even more enriching. Knowledgeable staff members passionately share stories and facts. They ensure that you leave with a deeper appreciation of the town’s maritime heritage.
The location is conveniently nestled in the heart of Chestertown. Visitors can easily combine a trip to the museum with other nearby attractions. Afterward, explore the area’s waterfront for picturesque views.
The Custom House allows you to step back in time. It’s a delightful experience that enriches your visit to Chestertown.
Address: 207 High St, Chestertown, MD 21620.
13. Wander through Wilmer Park
Wilmer Park is a scenic oasis in Chestertown. It offers beautiful views of the Chester River and is perfect for a peaceful day outdoors. You can enjoy a leisurely walk along the waterfront paths while taking in nature’s beauty.
The park features well-maintained gardens and picnic areas. Bring a blanket for a picnic with family and friends. The atmosphere is calm and relaxing, making it an ideal spot to unwind.
Children can play in the designated playground area, adding to the park’s family-friendly ambiance. Look for special events hosted in the park, like musical performances or community gatherings.
Wilmer Park is a great place for photography too. Capture lovely moments against the backdrop of the river. The colors of the sunset provide breathtaking views and perfect photo opportunities.
Wandering through Wilmer Park is a lovely way to spend your day. It connects you to the serenity and natural beauty of Chestertown.
Address: 885 High St, Chestertown, MD 21620.
14. Experience the RiverArts organization
RiverArts is a vibrant community organization that promotes the visual arts in Chestertown. Whether you are an artist or an admirer, RiverArts provides various opportunities to engage. You can join workshops, events, and exhibitions throughout the year.
Art classes range in level, catering to beginners and seasoned artists alike. You will learn new techniques while meeting fellow art enthusiasts. The atmosphere is collaborative and supportive, making it a friendly place to hone your skills.
Additionally, RiverArts hosts gallery exhibitions showcasing local artwork. The exhibits change regularly, so there’s always something fresh to see. Art lovers are encouraged to attend opening receptions to meet artists and share in the creative spirit.
The organization also participates in community events. These events connect artists with the public, fostering appreciation for the arts. You can experience the creativity that enriches the Chestertown community.
Engaging with RiverArts is an opportunity to connect with local talent. It’s a wonderful way to enrich your visit and appreciate the artistic culture of the area.
Address: 200 High St, Chestertown, MD 21620.
15. Visit the C & D Canal Museum
The C & D Canal Museum is located a bit further away but is worth the trip. This museum showcases the fascinating history of the Chesapeake and Delaware Canal. It’s an interactive space that highlights the importance of the canal for trade and transportation.
Inside, you will find a variety of exhibits and artifacts. These exhibits detail the construction and evolution of the canal over the years. You can learn about the challenges faced during its development and the impact on the community.
Guided tours are available, and the knowledgeable staff is eager to share insights. They bring the history of the canal to life through engaging storytelling. Visitors of all ages will find something to enjoy.
The museum is situated close to the water, providing beautiful views. After your visit, take a moment to appreciate the surrounding scenery. It’s a great photo opportunity too.
A trip to the C & D Canal Museum enriches your understanding of local history. It’s a memorable experience that showcases the region’s maritime heritage.
Address: 101 W Main St, Chesapeake City, MD 21915.
16. Attend a concert at the Church of the Brethren
The Church of the Brethren hosts a variety of musical performances throughout the year. This serene church provides a unique and tranquil atmosphere for concerts. You can enjoy everything from classical music to local bands, making it a diverse experience.
The acoustics within the church enhance the sound quality, making each performance special. Attendees often remark on the warmth and intimacy of the setting. It’s a lovely way to enjoy music in a peaceful environment.
Check their schedule for upcoming concerts, as they feature local talent and renowned artists alike. These events often draw crowds, so it’s wise to arrive early for good seating.
The church’s community-focused approach encourages everyone to attend. It’s a chance to meet fellow music lovers and connect with the local community.
Attending a concert at the Church of the Brethren is a delightful experience. Music in such a beautiful setting creates lasting memories.
Address: 550 N 4th St, Chestertown, MD 21620.
17. Check out local shops on Washington Avenue
Washington Avenue is lined with unique boutiques and quirky shops. It’s the perfect place to explore while discovering local crafts and products. Each shop has its own charm and personality, making it an enjoyable stroll.
From handcrafted jewelry to handmade artisan goods, you’ll find wonderful treasures. Take your time browsing and chatting with the shop owners. They are often very knowledgeable about their products and the local area.
Look out for seasonal sales and special events, as many shops host these throughout the year. Local artisans often showcase their work during these events, enhancing the shopping experience.
You may also find delightful cafes and eateries along Washington Avenue. Stop for a coffee or a snack to refuel during your shop-hopping adventure. It’s an excellent way to experience Chestertown’s local culture.
Exploring shops on Washington Avenue is a fun activity. You’ll leave with unique finds and memories of your visit.
Address: Washington Ave, Chestertown, MD 21620.
18. Visit the Kent County Fair
The Kent County Fair is a fantastic way to experience local culture and fun. Held annually, it gathers families and friends for a week of entertainment. The fair includes rides, games, and various attractions suitable for all ages.
Local vendors set up booths to showcase crafts, food, and agricultural products. You can taste delicious fair food while enjoying the lively atmosphere. There’s something for everyone, including livestock shows and carnival games.
Many families have traditions that involve attending the fair every year. It fosters a sense of community and celebration, bringing people from all walks of life together.
Check the fair’s schedule for live entertainment and activities. There are often contests and talent shows that highlight local talent.
Visiting the Kent County Fair is an enjoyable experience. You’ll create lasting memories while connecting with the heart of the community.
Address: 1030 Lathim Rd, Chestertown, MD 21620.
19. Take a bike ride along the Eastern Shore
Biking along the Eastern Shore is a great way to explore the beauty of the area. Scenic trails offer breathtaking views of the towns and waterways. Grab your bike and set off on a leisurely ride to soak in the fresh air and scenery.
The routes are suitable for both novice and experienced cyclists. You’ll find well-maintained paths that guide you through picturesque landscapes. Enjoy spotting local wildlife and the diverse flora along the way.
Make sure to stop at various lookout points for photos. The rolling hills and river views are stunning and perfect for memorable snapshots. It’s a wonderful way to experience the unique charm of the Eastern Shore.
Packing a picnic is a great idea, too—enjoy lunch in one of the many picturesque spots you find on your ride. Friendly cyclists often populate the trails, ensuring a welcoming atmosphere.
Cycling the Eastern Shore is more than just exercise; it’s an adventure that connects you to nature. It’s an enjoyable way to experience the local charm of the area.
Address: Eastern Shore, Chestertown, MD 21620.
20. Enjoy a meal at The Fish Whistle
The Fish Whistle is a popular spot for seafood lovers in Chestertown. This waterfront restaurant offers a cozy atmosphere along with stunning views of the Chester River. Dining here provides an inviting experience, perfect for a leisurely meal.
The menu features fresh, locally-sourced seafood, prepared with care. You can enjoy dishes such as fish tacos, crab cakes, and hearty chowders. The chefs take pride in offering quality meals that highlight local ingredients.
Besides seafood, The Fish Whistle also offers meat and vegetarian options, making it a versatile dining destination. Pair your meal with a glass of wine or a local craft beer for a complete experience.
While you’re waiting for your meal, take in the views from the outdoor seating area. The setting sun over the river creates a beautiful backdrop for your dining experience.
Dining at The Fish Whistle is not just a meal; it’s a delightful experience. You’ll leave satisfied and eager to return for more.
Address: 113 N. Water St, Chestertown, MD 21620.
21. Visit the Unity Lodge and Museum
The Unity Lodge and Museum is an intriguing stop for those interested in Masonic history. This lodge, steeped in tradition, showcases the rich background of Freemasonry. Visitors can learn about the symbols and values associated with the organization.
The museum hosts a collection of artifacts, documents, and displays detailing the evolution of Freemasonry in the area. Knowledgeable staff can provide guided tours, enriching your visit with fascinating facts.
Attending an event or open house at the lodge is a great opportunity to experience the community spirit. These events often welcome guests to learn more about the lodge’s role in society.
Exploring the Unity Lodge and Museum opens doors to understanding the values and history of local organizations. The historical significance of the Masonic Lodge resonates in its architecture and traditions.
Visiting here is a unique experience that adds depth to your understanding of the region’s history. It’s a memorable part of your Chestertown adventure.
Address: 6426 Rt 213, Chestertown, MD 21620.
22. Participate in First Friday Art Strolls
The First Friday Art Strolls are a delightful way to experience Chestertown’s vibrant art scene. Held on the first Friday of each month, the event showcases local artists, galleries, and studios. It’s an excellent opportunity to meet creators and discover unique artwork.
As you stroll through town, enjoy the lively atmosphere created by local music and entertainment. Many galleries host openings during the event, which means there’s always something new to see and experience.
The art stroll encourages community interaction and supports local talent. Chat with artists about their work and gain insights into their creative processes. The friendly ambiance makes everyone feel welcome.
Nearby shops and cafes often participate by offering specials during the event. Take a break to enjoy some refreshments as you explore the art scene.
Participating in the First Friday Art Stroll is an enjoyable evening for art enthusiasts and casual browsers alike. You’ll leave inspired and connected to the local arts community.
Address: High St, Chestertown, MD 21620.
23. Rent a bicycle and explore the area
Renting a bicycle is a fantastic way to discover Chestertown and its surrounding beauty. There are several local rental shops that provide quality bikes for all skill levels. Whether you’re a leisurely rider or an experienced cyclist, biking offers a unique perspective of the area.
There are beautiful trails and scenic roads leading to picturesque spots. Explore quaint neighborhoods, vibrant parks, and stunning waterfront views at your own pace. Feel the fresh air as you pedal through the charming streets.
Don’t forget to stop at various attractions along the way. You can take breaks to enjoy scenic spots or grab a bite at local restaurants. Interacting with the friendly locals can also enhance your experience.
Biking is not just an adventure; it’s also a great way to stay active while enjoying the landscape. The flexibility of a bike allows you to explore hidden gems that may not be accessible by car.
Renting a bicycle opens the door to an enriching journey through Chestertown. You’ll leave with fond memories of the beautiful surroundings.
Address: Bicycles shops located in various locations in Chestertown.
24. Experience the Shore Shakespeare Festival
The Shore Shakespeare Festival brings classic plays to life in a beautiful outdoor setting. Held annually, this festival allows you to enjoy the works of Shakespeare performed by talented actors. The festival’s mission is to make these timeless plays accessible to everyone.
Attendees are encouraged to bring picnic blankets and snacks. It creates a relaxed atmosphere where you can enjoy a beautiful evening under the stars. The production quality is high, with professional performances and vibrant costumes.
The festival often includes workshops and events, enhancing your understanding and appreciation of the material. It’s a wonderful way to engage with the arts in a friendly environment.
Viewers of all ages will find something to enjoy. The performances are entertaining, meaningful, and thought-provoking. They invite you to reflect on themes that resonate today.
Attending the Shore Shakespeare Festival is not just a show; it’s an experience that connects you to literature and community. Don’t miss the chance to be part of this unique cultural event.
Address: Chestertown, MD 21620.
25. Take a sunset cruise on the Chester River
A sunset cruise on the Chester River offers a breathtaking experience. As the day winds down, you can witness the changing colors of the sky reflected in the water. This picturesque setting is ideal for relaxation and connection with nature.
During the cruise, you may spot local wildlife, such as birds and fish. The peaceful sounds of the water create a calming atmosphere, perfect for unwinding after a busy day. Bring a camera to capture stunning views and create lasting memories.
Various local companies offer sunset cruises, complete with knowledgeable guides. They share interesting facts about the river and its history during your journey. This enhances the experience, making it both enjoyable and educational.
Don’t forget to bring snacks or drinks to savor during the cruise. Sharing this time with family or friends makes it even more special.
A sunset cruise on the Chester River is a delightful way to end your day. It leaves you with a deep sense of appreciation for the area’s natural beauty.
Address: Chester River, Chestertown, MD 21620.
Final Thoughts
Chestertown, Maryland, is a charming town bursting with culture, history, and outdoor activities. Whether you’re exploring local art, enjoying a live performance, or participating in community events, there’s always something to discover. The beauty of the Chester River and the surrounding landscapes enhances your experience, offering endless opportunities for relaxation and adventure.
With its rich heritage and vibrant local scene, Chestertown invites you to create lasting memories. If you’re looking for more inspiring places, check out our guide on places to visit in Maryland. This town’s warm community spirit will draw you back time and time again, making it a must-visit destination. Embrace the charm and consider exploring nearby areas like things to do in Solomons, MD to expand your adventures even further.