Chestertown, Maryland, is a charming little town located on the banks of the Chester River. It’s known for its beautiful historic buildings, friendly atmosphere, and vibrant arts scene. If you’re looking for a great place to spend a weekend or a day trip, Chestertown has plenty to offer. From riverside parks to unique shops, there’s something for everyone to enjoy.
Today, we’ll share some fun things to do in Chestertown. Whether you want to take a leisurely stroll along the waterfront or check out local art, you’ll find activities that make your visit special. Let’s take a look at what Chestertown has in store!
Things To Do In Chestertown Md
1. Stroll through the historic Chestertown waterfront and admire the picturesque views of the Chester River
Take a leisurely stroll along the historic waterfront of Chestertown, where the charm of colonial America meets vibrant modern life. The waterfront is a scenic treasure, providing beautiful views of the Chester River. As you walk, enjoy the fresh air and the serene sounds of water gently lapping at the shore.
Along the way, you will see historic buildings showcasing colonial architecture, which adds to the area’s charm. Many of these buildings house restaurants, shops, and galleries, making it the perfect place to stop for a coffee or a bite to eat. The atmosphere here is inviting and friendly, encouraging visitors to linger.
You can also spot local wildlife, including birds that frequent the riverbanks. Bring your camera to capture the vibrant colors of the sunset as it reflects off the water, creating a picturesque backdrop. It’s a popular spot for photographers and families alike.
The waterfront is not just about beautiful views; it also hosts various events throughout the year. Festivals and cultural events breathe life into the area, offering entertainment for all ages.
A walk along the Chestertown waterfront is an experience that combines nature, history, and community spirit. You will leave feeling refreshed and inspired.
Address: 101-199 High St, Chestertown, MD 21620.
2. Visit the Chestertown Marina to watch sailboats and enjoy the tranquil atmosphere
The Chestertown Marina is a peaceful retreat where you can watch sailboats glide across the Chester River. This tranquil location invites visitors to relax and soak in the stunning views. The sights and sounds of the marina create a calming atmosphere perfect for unwinding.
At the marina, you will often see local boaters preparing for a day on the water. The gentle lapping of waves and the rustle of sails in the wind set a serene backdrop for your visit. Take a seat on one of the benches to enjoy the scenery and perhaps even catch a glimpse of a sailing regatta.
If you’re lucky, you may witness fishermen bringing in their catch and vendors selling fresh seafood nearby. The marina is an ideal place to indulge in fresh local cuisine. Try some of the lobster rolls or fish tacos from the nearby eateries.
The marina is also a hub for water-based activities. Consider renting a kayak or paddleboard for an afternoon adventure on the river. It’s a fun way to explore the area while getting some exercise.
A visit to the Chestertown Marina is a delightful way to spend your day. With its beautiful scenery and peaceful vibes, it offers a refreshing escape from the hustle and bustle.
Address: 240-252 N Water St, Chestertown, MD 21620.
3. Explore the Dickey Park and its playground, perfect for families and kids
Dickey Park is a fantastic family destination in Chestertown. The park features a spacious playground that is perfect for children to climb, slide, and explore. It is a safe and fun environment where kids can make lasting memories while enjoying outdoor activities.
The park also offers plenty of green space for picnics and lounging. Bring your blanket and some snacks to enjoy a relaxing afternoon under the trees. You will often see families gathering here for birthday parties or simply to enjoy some fresh air.
Parents can also take advantage of the walking trails that wind through the park. These trails are excellent for a leisurely stroll or a brisk jog, allowing you to enjoy nature while keeping active. The playground and open spaces make it easy for children to run around freely.
Dickey Park is well-maintained and offers amenities such as restrooms and picnic tables, making visits convenient and pleasant. It’s the perfect spot for a family outing, gatherings with friends, or simply a peaceful day in nature.
Visiting Dickey Park is a delightful way to spend quality time with loved ones. The combination of play and relaxation makes it a must-visit destination for families in Chestertown.
Address: 125-199 S Maple Ave, Chestertown, MD 21620.
4. Take a guided tour of the historic district to learn about Chestertown’s colonial history
Experience the rich history of Chestertown by taking a guided tour of its historic district. This area is filled with fascinating stories and well-preserved buildings that date back to the colonial era. A knowledgeable guide will lead you through charming streets, sharing anecdotes and historical insights along the way.
You will visit significant landmarks, including the courthouse and various colonial homes, each with its unique story. The architecture is captivating, revealing the craftsmanship of the past. The tour provides an intimate look into the lives of residents during the 18th century, including how they contributed to the town’s development.
As you walk, pay attention to the beautiful gardens that adorn many properties. These gardens are a testament to the community’s commitment to preserving its historical roots. Photography opportunities abound as you explore the picturesque scenery.
The tour guides are typically enthusiastic and passionate about Chestertown’s history. Their stories bring the past to life, making history engaging for visitors of all ages. After the tour, you may feel inspired to explore more of the town on your own.
Taking a guided tour is a memorable and educational experience. It’s an excellent way for families and history buffs to connect with Chestertown’s vibrant heritage.
Address: 101 S Water St, Chestertown, MD 21620.
5. Visit the Chester River Packet Company for a scenic boat tour of the river
The Chester River Packet Company offers delightful boat tours that showcase the beauty of the Chester River. These scenic excursions allow you to experience the area’s natural wonders while enjoying the fresh breeze and stunning vistas. It’s a perfect way to unwind and connect with nature.
Onboard, knowledgeable guides share fascinating stories about local history and wildlife. You may spot various birds and marine life during your journey, as the river is home to many species. The guides enrich the experience with insights about the river’s ecosystem and its importance to the region.
The boat tours usually run during warm months, providing a perfect way to spend a sunny afternoon. You’ll be surrounded by lush greenery and picturesque scenery that make for fantastic photo opportunities. Whether you’re an avid photographer or just love nature, the views are sure to impress.
The Chester River Packet Company often offers special themed tours, such as sunset cruises. These outings provide a romantic and magical atmosphere as the sky transforms into a canvas of colors.
A boat tour with the Chester River Packet Company is an unforgettable experience that brings you closer to the stunning landscape of Chestertown. It’s a must-try for anyone visiting the area.
Address: 1669 Landing Rd, Chestertown, MD 21620.
6. Check out the artwork at the Chestertown Arts League galleries
Immerse yourself in the local art scene by visiting the Chestertown Arts League galleries. This vibrant organization showcases the talents of local artists through a rotating collection of exhibitions. Each visit offers something new, so you’ll always find fresh inspiration.
The galleries feature various art forms, including paintings, sculptures, and photography. You can engage with the artists and learn about their creative processes during exhibits or special events. Many artworks celebrate the beauty and culture of the Eastern Shore, providing a unique reflection of the region.
Visitors are welcome to purchase art pieces, making it a great opportunity to take home a piece of Chestertown. The galleries also offer art classes and workshops for those looking to unleash their creativity. It’s an excellent way to connect with the community and engage with your artistic side.
With changing exhibits and events, the Chestertown Arts League is a dynamic part of the town. It frequently hosts art openings, lectures, and other activities that emphasize the local arts culture. Be on the lookout for exciting events you can attend during your visit.
Whether you’re an art enthusiast or just curious, the Chestertown Arts League galleries are well worth a visit. You’ll leave inspired and with a deeper appreciation for the local arts community.
Address: 200 S Cross St, Chestertown, MD 21620.
7. Attend a performance at the Garfield Center for the Arts at the Prince Theatre
The Garfield Center for the Arts at the Prince Theatre is a hub of cultural activity in Chestertown. This historic venue hosts a variety of performances, including plays, concerts, and dance shows. Attending an event here is a fantastic way to experience the local arts scene.
The theater has a charming ambiance, providing an intimate setting for performances. The acoustics are remarkable, ensuring that you enjoy every word and note. Each performance brings together local talent and occasionally visiting artists, offering diverse entertainment for all audiences.
Check the schedule for upcoming shows, as there’s always something exciting happening. Whether you enjoy classic plays or contemporary productions, there’s likely to be an event that piques your interest. This theater is a great way to connect with the local community and the arts.
The Garfield Center also engages in educational programs for youth, inspiring the next generation of artists and performers. This involvement highlights the theater’s commitment to enriching the cultural landscape of Chestertown.
Experiencing a performance at the Garfield Center is an enjoyable outing. It’s a great way to support local arts and immerse yourself in the vibrant culture of this charming town.
Address: 210 High St, Chestertown, MD 21620.
8. Visit the Museum of Rural Life to understand the agricultural history of Kent County
The Museum of Rural Life offers a fascinating look into the agricultural history of Kent County. This quaint museum highlights the area’s farming heritage and the way of life for its residents over the centuries. Visitors can learn through exhibits, artifacts, and interactive displays.
As you explore, you will find displays on topics such as crop production, livestock management, and the evolution of farming equipment. The museum provides a unique perspective on how agriculture shaped the local community, economy, and environment.
The knowledgeable staff is eager to share their insights and stories about farming traditions in the area. They often host educational events and workshops related to agriculture, making the museum a lively hub for learning.
The museum’s location is scenic and serene, enhancing your visit as you stroll through its grounds. It’s an excellent spot for families and anyone interested in history and rural life. Kids can especially enjoy hands-on activities and demonstrations that bring farming to life.
Visiting the Museum of Rural Life is both informative and entertaining. It allows you to appreciate the rich agricultural legacy of Kent County and understand its significance to the community.
Address: 117-199 MD-213, Chestertown, MD 21620.
9. Walk through the Chestertown Farmers Market to support local vendors and enjoy fresh produce
The Chestertown Farmers Market is a lively community gathering held weekly. It features local vendors offering fresh produce, handmade goods, and unique crafts. The market is a fantastic place to support local farmers and artisans while enjoying the vibrant atmosphere.
As you wander through the stalls, you can find an array of seasonal fruits and vegetables, fresh flowers, and baked goods. Taste samples from vendors and discover unique items that you might not find elsewhere. Local honey, cheese, and preserves are popular favorites.
The market is not only a shopping destination but also a social event. You’ll see families, friends, and neighbors catching up and enjoying the lively environment. Live music often fills the air, creating a festive ambiance that enhances your shopping experience.
Visiting the farmers market is an excellent way to connect with the local community. It allows you to learn about the origins of your food and the hardworking individuals who cultivate it. You can also find unique handmade crafts and products that make great gifts.
Enjoying a morning at the Chestertown Farmers Market is a rewarding way to spend your day. It combines fresh food, community spirit, and a delightful atmosphere.
Address: 100 N Cross St, Chestertown, MD 21620.
10. Explore the Cannonball Mansion, an iconic historic home offering tours
The Cannonball Mansion is a stunning historical home located in Chestertown. This iconic structure has rich stories to tell and architectural beauty to admire. A visit here allows you to step back in time and learn about the lives of its past residents.
During guided tours, you can explore the beautifully preserved rooms, each filled with period furnishings and artwork. The guides share the mansion’s history, including fascinating tales of its construction and those who lived there. The mansion itself is a remarkable representation of the architectural styles of its time.
Visitors can also stroll through the manicured grounds, which offer lovely views of the surrounding area. This adds to the charm of the experience and creates a peaceful setting for reflection. The gardens are a great spot for photos, especially in bloom.
Cannonball Mansion often hosts special events, including art shows and educational programs. These activities enhance the understanding of the home’s significance in local history and culture.
A visit to the Cannonball Mansion is both enjoyable and enriching. It’s a wonderful way to appreciate the heritage of Chestertown while experiencing the beauty of a historic home.
Address: 330 High St, Chestertown, MD 21620.
11. Enjoy a picnic at Wilmer Park, overlooking the Chester River
Wilmer Park is an ideal spot for a relaxing picnic, offering stunning views of the Chester River. This beautiful park features plenty of grassy areas, picnic tables, and shady trees, creating a perfect setting for outdoor dining. Bring your favorite snacks or a packed lunch and enjoy the fresh air.
While picnicking, you can watch boats sail by on the river, creating a picturesque backdrop to your meal. The calming sound of the water and the sight of the passing boats make for a peaceful atmosphere. It’s a great place to unwind and enjoy quality time with family or friends.
The park also offers walking paths, allowing you to enjoy a leisurely stroll after your meal. The scenic trails wind through the park, providing opportunities for exploration and birdwatching. Children can play freely in the open spaces, making it a family-friendly destination.
Wilmer Park frequently hosts community events, including concerts and festivals. Participating in these events can enhance your picnic experience, adding excitement to your day.
Visiting Wilmer Park for a picnic is a delightful way to connect with nature and offer a break from your busy routine. You will leave feeling refreshed and invigorated.
Address: 538-698 Wilmer Park Rd, Chestertown, MD 21620.
12. Take a pottery or art class at the Kent County Arts Council
Engage your creativity by taking a pottery or art class at the Kent County Arts Council. The council offers various classes designed for all skill levels, making it a welcoming place for beginners and experienced artists alike. Explore different mediums and discover your artistic talents.
Classes are typically taught by talented local artists who provide hands-on instruction and guidance. You’ll learn new techniques and approaches, whether you’re interested in pottery, painting, or sculpture. The supportive atmosphere encourages exploration and personal expression.
Taking a class at the arts council is not just about creating art; it’s also an opportunity to meet like-minded individuals. Form lasting connections with fellow artists and foster a sense of community while enjoying creative pursuits.
The council often showcases the work of its members in exhibitions, allowing you to see the talent within the community. Participating in these classes can also help you develop your skills for future projects.
Whether you are a seasoned artist or just looking to try something new, attending an art class at the Kent County Arts Council is a fulfilling way to spend your time. You’ll leave feeling inspired and accomplished.
Address: 400 High St, Chestertown, MD 21620.
13. Discover local history at the Historical Society of Kent County
The Historical Society of Kent County is a treasure trove of local history. Visiting this site allows you to delve into the past and gain a deeper understanding of the region’s heritage. The society offers exhibits, archives, and resources that showcase Kent County’s fascinating stories.
As you explore, you will find documents, photographs, and artifacts that illustrate the lives of past residents. The exhibits often feature themes such as agriculture, industry, and social history, providing a well-rounded view of the community’s evolution.
The staff at the Historical Society is friendly and knowledgeable, eager to share insights and answer questions. They often organize events such as talks and workshops that further explore the county’s history, making learning interactive and enjoyable.
Whether you are a history buff or simply curious about the local area, this society offers a wealth of information. The archives are also open to researchers looking to uncover specific historical details.
Visiting the Historical Society of Kent County is an enriching experience that connects you to the area’s rich past. It’s a must-visit for anyone interested in understanding the community’s roots.
Address: 101 Church St, Chestertown, MD 21620.
14. Attend the Chestertown Jazz Festival for live music and cultural events
The Chestertown Jazz Festival is an annual event that celebrates jazz music and local culture. Held in September, this lively festival features diverse performances by talented musicians and bands. It’s a wonderful opportunity to immerse yourself in the rhythm and spirit of jazz.
Throughout the festival, several stages are set up in various venues, showcasing both local and national artists. Enjoy a range of performances from smooth jazz to energetic big band sounds, ensuring there’s something for every jazz aficionado.
The festival creates a festive atmosphere with food vendors, art displays, and activities for all ages. It’s a fantastic way to enjoy great food while listening to live music. Many families attend, making it a joyful community celebration.
Additionally, the festival often includes workshops and jam sessions, allowing attendees to interact with musicians and learn more about the art of jazz. These educational opportunities make the festival even more enriching.
Attending the Chestertown Jazz Festival is an unforgettable experience that promotes community spirit and appreciation for the arts. Mark your calendar and enjoy a fun-filled weekend of music and culture!
Address: Various locations in Chestertown, MD 21620.
15. Go kayaking or paddleboarding on the Chester River for an adventurous outing
For adventure seekers, kayaking or paddleboarding on the Chester River is an absolute must. The river’s calm waters provide an excellent setting for both beginners and experienced paddlers alike. Renting equipment is easy, and several local outfitters offer rentals and guided tours.
As you paddle along the river, you’ll enjoy stunning views of the surrounding nature. Keep an eye out for local wildlife, including birds and fish that inhabit the area. The experience of being on the water allows you to connect with nature in a unique way.
Kayaking and paddleboarding are fantastic ways to get some exercise while exploring the beauty of Kent County. You can choose to take your time and enjoy the scenery or challenge yourself with more vigorous paddling.
Whether you go solo or join a group, the experience promises fun and adventure. For those looking for a more relaxed outing, consider taking a guided tour that combines education and scenic exploration.
Paddling on the Chester River offers a thrilling way to spend a day outdoors. Embrace the adventure and make lasting memories on the water!
Address: 2000 Garrison Rd, Chestertown, MD 21620.
16. Indulge in local cuisine at popular restaurants like The Fish Whistle
When in Chestertown, dining at local restaurants is a highlight of the visit. The Fish Whistle is a popular spot known for its delicious seafood and seasonal dishes. Located right on the waterfront, it offers a picturesque setting to enjoy a meal while watching the boats pass.
The menu features a variety of seafood options, including fresh catches of the day, crab cakes, and lobster rolls. All dishes are prepared with locally sourced ingredients to ensure quality and flavor. You can also find salads, pastas, and vegetarian options, catering to all tastes.
Aside from the food, The Fish Whistle boasts a friendly and laid-back atmosphere. The staff is welcoming and eager to share the best menu choices, making it a great place for families, couples, and groups of friends.
Don’t forget to try their craft cocktails or local beers to complement your meal. Enjoy your dining experience outdoors on the patio for an added pleasure of the scenic views.
Dining at The Fish Whistle allows you to savor the flavors of Chestertown. It’s a delightful way to indulge in local cuisine and create lasting memories over a great meal.
Address: 143 N Water St, Chestertown, MD 21620.
17. Explore the campus of Washington College, a beautiful liberal arts college
Washington College is a picturesque liberal arts college located in Chestertown. Taking a stroll through its beautiful campus is a delightful experience. The historic buildings and well-kept gardens create a charming environment that reflects the college’s rich heritage.
As you walk around, you can appreciate the architecture of the various buildings, many of which date back to the founding of the college in 1782. The campus features peaceful green spaces, ideal for relaxing under a tree or taking in the scenery.
Washington College often hosts events open to the public, including lectures, concerts, and art exhibitions. Attending these events allows you to engage with students and faculty while experiencing the vibrant intellectual community.
Consider visiting the college’s library, a valuable resource filled with historical documents and archives. It’s a great spot for those interested in research or simply enjoying a quiet place to read.
Exploring Washington College is an enriching experience that highlights the importance of education and culture in Chestertown. You’ll leave feeling inspired by the beautiful surroundings and academic spirit.
Address: 300 Washington Ave, Chestertown, MD 21620.
18. Participate in the annual Chestertown Tea Party Festival, celebrating local history
The annual Chestertown Tea Party Festival is a unique and lively event that celebrates the town’s historical significance. Held in May, this festival commemorates the 1774 tea party protest against British taxation. Attending this event allows you to step back in time and immerse yourself in local history.
The festival features reenactments, live music, arts and crafts vendors, and delicious food stalls. Visitors of all ages can enjoy activities such as games, face painting, and historic demonstrations. The atmosphere buzzes with excitement as the community comes together to celebrate.
Throughout the weekend, you can enjoy an array of performances, from local musicians to theatrical presentations that bring history to life. The reenactment of the tea party itself is a highlight, allowing participants to witness this important event in action.
This festival is not just about celebrating history; it also fosters community spirit and pride. You’ll meet friendly locals and enjoy the charm of Chestertown.
Participating in the Chestertown Tea Party Festival is an unforgettable experience that combines fun, learning, and local culture. It’s a must-visit event for anyone in the area.
Address: 300 N Cross St, Chestertown, MD 21620.
19. Visit the nearby Eastern Shore Wine Trail for wine tasting and tours
For wine enthusiasts, the Eastern Shore Wine Trail offers a delightful experience of exploration and tasting. Located just a short drive from Chestertown, this wine trail features several local vineyards and wineries, each with its unique offerings. Gather friends for a fun day of wine tasting and scenic views.
The wineries provide guided tours that take you through the vineyards and cellar, showcasing the wine-making process from grape to bottle. Many vineyards offer tastings of their wines, providing an opportunity to sample a variety of blends and styles.
The beautiful landscapes surrounding the wineries make for an ideal day out in nature. You can enjoy picnicking on the grounds or relaxing with a glass of wine while taking in the picturesque surroundings.
Events such as wine festivals and seasonal celebrations are often held along the trail, making visits even more special. These events provide a festive atmosphere and a chance to meet fellow wine lovers.
Exploring the Eastern Shore Wine Trail is a fun and enjoyable experience, whether you are a seasoned wine connoisseur or just looking for a pleasant day trip. Cheers to great wines and new memories!
Address: Various wineries along the Eastern Shore, MD 21620.
20. Walk the scenic trails at the nearby Sultana Education Foundation’s interim headquarters and explore local ecology
The Sultana Education Foundation is an excellent place to explore local ecology through its scenic trails. Located near Chestertown, the foundation offers educational programs about the environment, history, and culture of the Chesapeake Bay area. Walking the trails is a fantastic way to connect with nature.
The trails wind through beautiful woodlands and along the river, providing opportunities to see various plants and wildlife. The peaceful surroundings make it an ideal spot for hiking, birdwatching, or simply enjoying the tranquility of nature.
The Sultana Foundation often hosts events and programs that focus on environmental education, including guided nature walks and family activities. These programs allow visitors to learn about the local ecosystem while having fun outdoors.
Whether you choose to hike, learn, or participate in events, you’ll leave with a greater appreciation for the environment and its importance. The foundation provides a welcoming atmosphere for individuals and families.
Walking the scenic trails at the Sultana Education Foundation is a refreshing experience. It’s a wonderful way to engage with nature and the community.
Address: 200-298 Water St, Chestertown, MD 21620.
Final Thoughts
Chestertown, Maryland, is a gem filled with history, creativity, and adventure. Whether you’re strolling along the waterfront, attending local festivals, or exploring its vibrant art scene, there’s something for everyone to enjoy. The community spirit shines through in its events, markets, and dining options, making every visit memorable.
As you experience the charm of this beautiful town, you’ll create lasting memories that draw you back time and time again. Chestertown is a place to relax, explore, and connect with nature and history. The beauty of the Chesapeake Bay and the warmth of its people ensure that your stay is fulfilling and enriching.
For further exploration beyond Chestertown, consider checking out exciting things to do in Cambridge, Maryland, or visit the vibrant attractions in Aberdeen, Maryland. These locations offer their unique blend of experiences that are sure to enrich your travels.