Chestertown, Maryland, is a charming town filled with rich history and beautiful scenery. Nestled along the Chester River, this small community has something for everyone, from outdoor activities to cultural experiences. Whether you’re a local or just visiting, you’ll find plenty of fun activities to enjoy in this quaint town.
Today, we will look at some of the best things to do in Chestertown. From visiting unique shops to taking in scenic views, there is no shortage of exciting ways to spend your time. Get ready to uncover all the great experiences Chestertown has to offer!
Things To Do In Chestertown Md
1. Stroll Through the Historic Chestertown Waterfront
The Chestertown waterfront is a picturesque area that reflects the charm of this historic town. As you stroll along the Chester River, you can admire the beauty of the water and the quaint buildings nearby. The walk is refreshing and offers opportunities to take stunning photos along the way.
Enjoy the views of boats gently bobbing in the river. The waterfront is a great place for birdwatching too. You might spot some local wildlife, including ducks and other birds. This scenic landscape creates a calming atmosphere.
Take a moment to sit on a bench and soak in the serenity. The sound of water lapping against the shore is soothing. It’s also a perfect spot to indulge in a good book or simply relax. The surrounding gardens add to the beauty of this area.
Along the waterfront, you’ll find small shops and eateries. Stop by for a delicious snack or a refreshing drink. Enjoying local treats while taking in the view is a wonderful way to enhance your experience.
Whether you’re a local or just visiting, a walk along the Chestertown waterfront is a must. It’s a perfect blend of history, nature, and relaxation.
Address: 100 S Water St, Chestertown, MD 21620.
2. Visit the Chesapeake Bay Maritime Museum
The Chesapeake Bay Maritime Museum is an educational gem highlighting the region’s rich maritime history. Create wonderful memories as you immerse yourself in local culture and heritage. It’s more than a museum; it’s a journey through time.
Exhibits showcase artifacts ranging from historic boats to navigational tools. The hands-on displays engage visitors of all ages. You can learn about the tools of the trade used by local fishermen and boat builders.
Don’t miss the chance to take a guided tour. Knowledgeable staff share fascinating stories about the Bay and its significance. Their passion for history makes the experience highly engaging.
In the outdoor area, you can view restored vessels. This includes skipjacks and other traditional crafts. Witnessing these boats firsthand connects you to the maritime legacy of the area.
Visit the museum gift shop for unique items that celebrate the bay’s culture. It’s an excellent place to find souvenirs that remind you of your visit.
Address: 213 N Talbot St, St Michaels, MD 21663.
3. Explore the Chestertown Farmers Market
The Chestertown Farmers Market is a delightful experience for all ages. Gather fresh produce directly from local farmers. The market is lively and full of energy, making it a great place to visit on Saturday mornings.
You’ll find a wide selection of fruits and vegetables that are in season. The vendors are always happy to share tips on how to prepare their goods. In addition to produce, local artisans offer crafts, flowers, and homemade goods.
Enjoy sampling cheeses, breads, and baked treats from various local vendors. The aromas and flavors create a festive atmosphere that is hard to resist. You may discover your new favorite snack.
Bring the family along and make it a mini outing. Kids can learn about food sources and meet the farmers who grow their food. It’s a fun, educational experience that supports the local community.
The inviting environment, coupled with live music, makes for a wonderful Saturday morning. Enjoy the local vibe and mingle with community members.
Address: 100 N Cross St, Chestertown, MD 21620.
4. Enjoy a Guided Tour of the Historic District of Chestertown
Step back in time with a guided tour of the historic district of Chestertown. This charming area is filled with beautiful colonial architecture and rich history. Knowledgeable guides share wonderful stories about the town’s past.
As you walk through the streets, you’ll see landmarks dating back to the 18th century. Many buildings have interesting architectural details that reflect their historical significance. Keep your camera ready for excellent photo opportunities.
Guided tours typically cover prominent sites, including the waterfront and historic homes. You will learn about important figures in Chestertown’s history. Each step offers a new glimpse into the narrative of this fascinating town.
The tours are designed to be engaging, with plenty of chances to ask questions. The guides are enthusiastic and knowledgeable, making history fun. Their passion for the town is infectious.
By the end of the tour, you will gain a deeper appreciation of Chestertown’s heritage. Don’t miss this chance to connect with the past in such a vibrant area.
Address: 400 High St, Chestertown, MD 21620.
5. Attend a Performance at the Garfield Center for the Arts
The Garfield Center for the Arts is a cultural highlight in Chestertown. It’s a hub for creativity and performance, offering something for everyone. Whether you enjoy theater, music, or art, there’s an event for you.
The center hosts a variety of performances throughout the year. Local actors and musicians showcase their talents in a cozy setting. The intimate environment allows you to connect with the performers and enjoy the art up close.
Check their calendar for upcoming shows. You may find everything from classic plays to modern productions. Special events and community gatherings are often part of the lineup, bringing the community together.
The venue itself is charming and well-maintained. Historic details blend beautifully with modern amenities, creating a perfect atmosphere for an enjoyable evening out. Don’t forget to grab a snack or drink during intermission.
If you love the arts, this is the place to be. Plan a night out at the Garfield Center and experience the local talent firsthand.
Address: 210 High St, Chestertown, MD 21620.
6. Go Kayaking or Paddleboarding on the Chester River
Adventure awaits as you go kayaking or paddleboarding on the Chester River. This calm waterway is perfect for both beginners and experienced paddlers. Enjoy the beauty of nature as you glide along the surface.
Rentals are available at local shops, making it easy to start your journey. Whether you choose a kayak or a paddleboard, you’ll have a blast exploring the scenic routes. Keep an eye out for wildlife, including birds and fish.
Paddling on the Chester River allows you to appreciate the peaceful surroundings. You can soak in the natural beauty of the riverbanks and enjoy the local flora and fauna. It’s a fantastic way to unwind and connect with nature.
The river offers various routes, catering to all skill levels. You can take a leisurely paddle or challenge yourself with longer distances. If you prefer a guided experience, options are available to enhance your adventure.
Kayaking or paddleboarding is a fun activity for families and friends. Make unforgettable memories while enjoying the great outdoors.
Address: 200 N Water St, Chestertown, MD 21620.
7. Check Out the Local Shops and Boutiques on High Street
High Street is the heart of Chestertown’s shopping scene. Explore the diverse array of local shops and boutiques. Each store has its own unique charm and offerings, making it a delightful experience for shoppers.
Stroll from shop to shop, discovering handmade goods, clothing, and local art. You’ll find something special at every turn. The friendly shopkeepers are eager to share their stories and assist you in finding the perfect item.
Take your time browsing through the eclectic mix of stores. From antique shops to specialty food stores, the variety keeps things interesting. You might find treasures that reflect the local culture.
Many boutiques also feature local artisans. This supports the community and allows you to take home a piece of Chestertown with you. Don’t forget to ask about any upcoming events or special sales.
The vibrant atmosphere on High Street makes it a great place to spend an afternoon. Grab a coffee and enjoy the local vibe—there’s always something happening!
Address: 100 High St, Chestertown, MD 21620.
8. Visit the Dickey Park for a Relaxing Picnic
Dickey Park is a community gem in Chestertown, perfect for a relaxing picnic. This beautiful park features expansive green spaces and plenty of shady spots. It’s an ideal location for enjoying a meal outdoors with family and friends.
The park is equipped with picnic tables and benches. Bring your favorite snacks or a homemade lunch and feast amid nature. The peaceful atmosphere enhances the picnic experience, allowing you to unwind and enjoy the scenery.
Children will love the playground area, offering fun for all ages. Let them play while you lounge in the sun or read a book. It’s a perfect balance of activity and relaxation.
Take a stroll along the paved paths within the park. You can enjoy a leisurely walk, admiring the well-kept landscaping. If you’re lucky, you might catch a glimpse of local wildlife like squirrels and birds.
Dickey Park is a space for community gatherings, sporting events, and relaxation. Don’t miss out on the chance to enjoy a beautiful day outdoors!
Address: 400 N Water St, Chestertown, MD 21620.
9. Discover the History of Washington College with a Campus Tour
Washington College offers a fascinating glimpse into educational history. Founded in 1782, it is one of the oldest colleges in the United States. A campus tour allows you to explore both the stunning architecture and the institution’s storied past.
The college features beautiful historic buildings. Stroll through the well-maintained grounds and soak in the vibrant college atmosphere. You’ll see students engaged in various activities, amplifying the sense of community.
Your tour guide will share interesting facts about the college’s heritage. Learn about notable alumni and their contributions to history. Each story adds a rich layer to the experience, connecting you with the college’s legacy.
Visit the Brown Advisory Admissions House during your tour. This facility offers insights into the admissions process, making it a helpful stop for prospective students. Discover what makes Washington College unique among institutions of higher learning.
Taking a campus tour at Washington College is enlightening and enjoyable. It’s a wonderful way to appreciate both history and education within Chestertown.
Address: 300 Washington Ave, Chestertown, MD 21620.
10. Explore the Beautiful Landscapes at the Eastern Shore Land Conservancy
The Eastern Shore Land Conservancy provides access to pristine landscapes. Committed to preservation, the conservancy protects the natural beauty of the area. This is a wonderful spot for nature lovers and outdoor enthusiasts alike.
Take advantage of the hiking trails that wind through scenic woodlands and fields. Each trail offers unique views of the coastal landscape. Enjoy the tranquility of nature as you hike at your own pace.
Wildlife enthusiasts will be delighted by the variety of species in the area. Bring your binoculars for birdwatching or try to spot local flora and fauna. There’s always something new to discover.
The conservancy also offers educational programs and events. Participate to learn more about local ecology and conservation efforts. Engaging with these activities enriches your appreciation of the environment.
Visiting the Eastern Shore Land Conservancy is a delightful way to spend the day outside. Immerse yourself in nature, take deep breaths, and rejuvenate your spirit.
Address: 210 S Talbot St, Chestertown, MD 21620.
11. Enjoy a Scenic Bike Ride on the Chestertown Rail Trail
The Chestertown Rail Trail offers a fantastic opportunity for biking enthusiasts. This scenic trail, stretching several miles, follows a former railway route. It provides easy access to beautiful views and peaceful surroundings.
As you ride, you’ll pass through picturesque landscapes, including wooded areas and open fields. The trail is well-maintained, making it suitable for riders of all ages and abilities. Enjoy the fresh air and the sounds of nature along the way.
Take breaks at various points to appreciate the scenery. There are also benches for resting if you need to catch your breath. Pack a picnic and make a day out of it with family or friends.
The rail trail is perfect for solo adventures too. Whether you’re looking for exercise or a leisurely ride, it caters to all preferences. Bring your camera to capture the stunning views along the way.
Each ride on the Chestertown Rail Trail leaves you feeling rejuvenated. It’s a great way to explore the outdoors and enjoy local nature.
Address: 100 Washington Ave, Chestertown, MD 21620.
12. Attend the Chestertown Tea Party Festival During the Annual Event
The Chestertown Tea Party Festival is a lively and unique event celebrating local heritage. This annual festival attracts visitors from all around. It’s a fun-filled way to learn about the town’s connection to the American Revolution.
Participate in various activities during the weekend-long celebration. Enjoy live music, craft demonstrations, and delicious food vendors. This event is perfect for families looking for entertainment and education.
The highlight of the festival is the reenactment of the historical tea party. Local actors bring the past to life in an exciting performance. It engages spectators, making history relevant and fun for everyone.
Browse local artisans selling handcrafted goods. You might find unique souvenirs to take home that encapsulate the spirit of Chestertown. Support local businesses while enjoying the festive atmosphere.
Attending the Chestertown Tea Party Festival creates lasting memories. It’s an event not to miss—it encapsulates the town’s history and vibrancy.
Address: 100 S Water St, Chestertown, MD 21620.
13. Try Your Luck Fishing Off the Chestertown Pier
The Chestertown Pier is a delightful spot for fishing enthusiasts. Located along the Chester River, it offers a relaxing atmosphere to cast your line. Enjoy the peace of the water as you await the catch of the day.
Bring your fishing gear and settle into a comfortable spot on the pier. The scenery is beautiful, with birds flying overhead and boats drifting by. It’s a perfect way to unwind and connect with nature.
The pier is accessible and welcoming for all skill levels. Whether you’re a seasoned angler or trying fishing for the first time, you’ll have fun. Locals often share tips and advice, making it a friendly environment.
Catch and release is encouraged, adding to the sustainability of the area. You might reel in a variety of fish, contributing to an enjoyable experience. Fishing is also a great chance for bonding with family or friends.
Visiting the Chestertown Pier for fishing is about more than just the catch; it’s about enjoying the outdoors and memorable moments.
Address: 300 S Water St, Chestertown, MD 21620.
14. Visit the Old Chestertown Court House, a Local Historic Landmark
The Old Chestertown Court House is a local historic landmark filled with rich history. Built in 1796, this building holds stories from the town’s past. A visit allows you to connect with the heritage of Chestertown.
As you approach the courthouse, admire its elegant architecture. The structure reflects the colonial style and is a landmark in the community. You can imagine the historical events that have taken place within its walls.
Guided tours are available, providing fascinating details about its history and function. Knowledgeable guides will share stories about notable cases and figures associated with the courthouse. Each tale adds depth to your visit.
Surrounding the courthouse, you’ll find beautiful gardens. It’s a lovely spot to relax after your tour. Take in the atmosphere, where history meets modern life.
Visiting the Old Chestertown Court House is an educational experience. It enhances your appreciation of the town and its historical significance.
Address: 101 N Cross St, Chestertown, MD 21620.
15. Participate in Workshops at the Kent County Arts Council
The Kent County Arts Council offers a range of workshops promoting creativity. Whether you’re a beginner or an experienced artist, there’s something for everyone. Join a class and explore your artistic talents in a supportive environment.
Workshops cover various mediums, such as painting, pottery, and photography. Each session provides hands-on experience with guidance from talented instructors. It’s an engaging way to learn and create.
Participating in these workshops allows you to express your creativity. You might make new friends while gaining skills in the arts. The atmosphere is welcoming, encouraging you to experiment and grow.
Throughout the year, the arts council also hosts special events. This includes exhibitions showcasing local artists. Attending these events further enriches your understanding of the local art scene.
Joining a workshop at the Kent County Arts Council is an excellent way to immerse yourself in creativity. Discover the joy of making art in a nurturing space.
Address: 205 Nomberie St, Chestertown, MD 21620.
16. Relax at Wilmer Park with its Waterfront Views and Walking Trails
Wilmer Park is a serene escape in Chestertown, perfect for relaxation. With its waterfront views and well-maintained walking trails, it invites visitors to spend time in nature. This park is a great place for families and individuals alike.
The scenic trails wind along the riverbank, providing beautiful vistas of the Chester River. Stroll at your own pace, taking in the surroundings. You might spot ducks and other wildlife along the way!
Parks often host community events, bringing people together to enjoy the outdoors. Check the calendar for live music, festivals, and seasonal celebrations. These events create a lively atmosphere full of energy.
Packs a picnic to enjoy on the grassy areas of the park. There are plenty of benches if you prefer a more comfortable spot. The peaceful environment is perfect for reflection or reading.
Relaxing at Wilmer Park is a wonderful way to unwind. Embrace the natural beauty and enjoy quality time with loved ones.
Address: 500 S Water St, Chestertown, MD 21620.
17. Visit the Historical Society of Kent County for Insights into Local History
The Historical Society of Kent County offers a deep dive into local history. This small museum houses a wealth of information and artifacts. Explore the exhibits showcasing Kent County’s rich heritage.
Guided tours are available, providing personal insights into the displays. Friendly staff members are passionate about sharing the stories behind the artifacts. Their knowledge enriches your understanding of the area.
The museum often hosts special events and lectures. These gatherings bring the community together to discuss historical topics and celebrate local culture. It’s a wonderful way to engage with others who share your interests.
While visiting, be sure to ask about their archives. The society preserves many historical records, making it a valuable resource for researchers and genealogy enthusiasts.
Discovering history at the Historical Society of Kent County is an enlightening experience. It connects you to the community’s past in meaningful ways.
Address: 301 High St, Chestertown, MD 21620.
18. Take a Boat Tour to Experience the Beautiful Scenery of the Chester River
Taking a boat tour on the Chester River is a fantastic way to absorb the natural beauty of the area. As you glide through the water, you’ll be treated to stunning views of both the landscape and local wildlife. It’s a relaxing experience that brings you closer to nature.
Local companies offer various tour options, including sunset cruises and wildlife spotting adventures. Guides share interesting insights about the area’s ecology and history, enhancing your knowledge while you enjoy the sights.
Bring your camera to capture the scenic moments along the way. The riverbanks are lined with picturesque homes, lush greenery, and charming wildlife. Keep an eye out for eagles and ospreys soaring above!
Boat tours typically cater to individuals, families, and groups. It’s an excellent way to celebrate special occasions, like birthdays or family reunions, on the water. You may even have the chance to jump in and swim during summer months!
A boat tour on the Chester River is a perfect way to experience tranquility and beauty. Don’t miss the chance to see the area from a fresh perspective.
Address: 100 S Water St, Chestertown, MD 21620.
19. Join a Winery Tour at a Local Vineyard for Wine Tastings
A winery tour in the Chestertown area offers a delightful experience for wine enthusiasts. Local vineyards produce high-quality wines that reflect the unique terroir of Maryland. Eagerly participate in tastings, and discover your new favorite varieties!
During the tour, knowledgeable staff provide insights into the winemaking process. You’ll learn about the different grape varieties grown in the region. This educational aspect enriches your appreciation of the wines.
Many vineyards have beautiful grounds for walking or relaxing. Enjoy the scenic views as you sip your wine, creating a serene atmosphere. It’s an ideal setting for a romantic outing or a fun day with friends.
Some wineries also offer special events throughout the year. This includes themed dinners, festivals, and live music. Engaging with the local community enhances the experience and creates lasting memories.
Visiting a local vineyard for a wine tour is not only enjoyable but educational. It’s an opportunity to sip, savor, and enjoy the enchanting landscapes of the region.
Address: 1234 Old St, Chestertown, MD 21620.
20. Enjoy Live Music at One of the Downtown Bars or Restaurants Featuring Local Bands
Dive into the vibrant nightlife of Chestertown by enjoying live music at local bars and restaurants. The downtown area is full of venues hosting talented musicians. Experience the joy of listening to live performances while sipping on your favorite drink.
Many establishments feature local bands, adding a unique touch to the atmosphere. You’ll find a variety of music styles, from jazz to folk, making it easy to find something you love. The intimate settings offer a great opportunity to connect with the performers.
Dance the night away or simply sit back and enjoy the show. The lively energy of the audience adds to the fun. It’s a perfect way to bond with friends or make new ones.
Don’t forget to check the event schedule for special performances and themes. There’s often something happening in the evenings, turning the downtown area into an entertainment hub.
Experiencing live music in Chestertown is an engaging way to unwind after a day of exploring. Soak in the local culture while enjoying fantastic tunes!
Address: 300 High St, Chestertown, MD 21620.
Final Thoughts
Chestertown is a charming destination rich in history and natural beauty. From the picturesque waterfront to local eateries and thriving arts, there’s something for everyone. Each activity offers a unique opportunity to connect with the community and explore the area’s heritage. If you’re interested in exploring other charming places, check out things to do in Cambridge MD or things to do in Aberdeen MD for more awesome experiences!
Whether you are enjoying a peaceful day in the park, participating in local events, or learning about the fascinating history at museums, Chestertown invites you to create lasting memories. Embrace the charm and warmth of this beautiful town, and you’ll find it irresistible.