34 Must Visit Places In Chestertown

Chestertown, Maryland, is a hidden gem waiting to be explored. This charming town, located on the Chester River, offers a mix of history, culture, and natural beauty. Whether you're a history buff, nature lover, or foodie, Chestertown has something for everyone. Wander through its historic district, where colonial architecture tells stories of the past. Enjoy a peaceful stroll along the riverfront or take a boat tour to see the town from a different perspective. Don't miss the local farmers' market, where you can sample fresh produce and homemade goodies. Ready to discover the best spots in Chestertown? Let's dive in!

Historical Landmarks

Chestertown, Maryland, is a treasure trove of historical landmarks. This charming town offers a glimpse into America's past with its well-preserved sites.

1. Washington College
   Founded in 1782, Washington College is one of the oldest colleges in the United States. Its picturesque campus and historic buildings make it a must-visit.

2. Chestertown Historic District
   Walk through the Chestertown Historic District to see beautifully preserved 18th-century homes and buildings. The district is a testament to the town's rich history.

3. White Swan Tavern
   Built in 1733, the White Swan Tavern offers a peek into colonial life. Today, it serves as a bed and breakfast, allowing visitors to experience history firsthand.

4. Custom House
   This 1746 building once served as a customs office. Now, it houses the Starr Center for the Study of the American Experience, offering educational exhibits.

Natural Attractions

Nature lovers will find plenty to admire in Chestertown. The town's natural attractions provide a peaceful escape from the hustle and bustle.

5. Eastern Neck National Wildlife Refuge
   This 2,285-acre refuge is a haven for birdwatchers and nature enthusiasts. It offers hiking trails, observation decks, and stunning views of the Chesapeake Bay.

6. Wilmer Park
   Located along the Chester River, Wilmer Park is perfect for picnics, walking, and enjoying waterfront views. The park also hosts various events throughout the year.

7. Turner's Creek Park
   Turner's Creek Park features scenic trails, a historic granary, and a beautiful waterfront. It's an ideal spot for hiking, fishing, or simply relaxing.

8. Betterton Beach
   A short drive from Chestertown, Betterton Beach offers sandy shores and calm waters. It's a great place for swimming, sunbathing, and beachcombing.

Cultural Experiences

Chestertown's vibrant cultural scene includes art galleries, theaters, and festivals that celebrate the town's creative spirit.

9. Garfield Center for the Arts
   Housed in a historic theater, the Garfield Center for the Arts hosts plays, concerts, and other performances. It's a cultural hub for the community.

10. Chestertown RiverArts
    This community arts center features rotating exhibits, workshops, and classes. It's a great place to explore local art and meet talented artists.

11. Chestertown Tea Party Festival
    Held annually, the Chestertown Tea Party Festival commemorates the town's colonial history with reenactments, parades, and family-friendly activities.

12. National Music Festival
    Every June, the National Music Festival brings world-class musicians to Chestertown. Enjoy concerts, masterclasses, and open rehearsals.

Unique Shops and Eateries

Chestertown's unique shops and eateries offer a delightful mix of local flavors and one-of-a-kind finds.

13. Evergrain Bread Company
    This bakery is famous for its freshly baked bread, pastries, and coffee. It's a perfect spot for breakfast or a midday treat.

14. Twigs & Teacups
    A charming gift shop, Twigs & Teacups offers a variety of unique items, from home decor to jewelry. It's a great place to find a special souvenir.

15. The Lemon Leaf Cafe
    Known for its delicious comfort food, The Lemon Leaf Cafe is a local favorite. Try their famous crab cakes or a hearty bowl of soup.

16. The Bookplate
    This independent bookstore offers a curated selection of new and used books. It's a cozy spot to browse and find your next great read.

Outdoor Activities

For those who love outdoor adventures, Chestertown offers plenty of options to get active and enjoy the great outdoors.

17. Chester River Kayak Adventures
    Explore the Chester River by kayak or paddleboard. Chester River Kayak Adventures offers rentals and guided tours for all skill levels.

18. Hiking at Sassafras Natural Resource Management Area
    This area features miles of trails through forests and wetlands. It's a great place for hiking, birdwatching, and enjoying nature.

19. Fishing at Millington Wildlife Management Area
    Anglers will love fishing at Millington Wildlife Management Area. The area offers freshwater fishing opportunities in a serene setting.

20. Cycling the Kent County Scenic Byway
    Take a bike ride along the Kent County Scenic Byway. The route offers beautiful views of the countryside and historic sites.

Family-Friendly Fun

Chestertown is a great destination for families, with plenty of activities to keep kids entertained.

21. Kent County Public Library
    The Kent County Public Library offers a variety of programs and activities for children. It's a great place to spend a rainy afternoon.

22. Playground at Wilmer Park
    Wilmer Park features a playground that's perfect for kids. They can burn off energy while parents enjoy the scenic views.

23. Chestertown Farmers Market
    Held every Saturday, the Chestertown Farmers Market offers fresh produce, baked goods, and crafts. It's a fun outing for the whole family.

24. Rock Hall Beach
    Just a short drive from Chestertown, Rock Hall Beach offers calm waters and sandy shores. It's a great spot for a family beach day.

Seasonal Events

Chestertown hosts a variety of seasonal events that draw visitors from near and far. These events showcase the town's community spirit and offer fun for all ages.

25. Chestertown Harry Potter Festival
    Fans of the wizarding world will love the Chestertown Harry Potter Festival. The event features themed activities, costume contests, and more.

26. Downrigging Weekend
    This annual event celebrates maritime heritage with tall ship tours, sails, and waterfront activities. It's a unique experience for all ages.

27. Chestertown Jazz Festival
    Held every September, the Chestertown Jazz Festival brings talented musicians to town for a weekend of great music and good times.

28. Dickens of a Christmas
    Celebrate the holiday season with Dickens of a Christmas. The event features carolers, horse-drawn carriage rides, and festive decorations.

Educational Experiences

Chestertown offers several educational experiences that are both fun and informative. These attractions provide a deeper understanding of the area's history and culture.

29. Kent County Historical Society
    Visit the Kent County Historical Society to learn about the region's past. The society offers exhibits, lectures, and walking tours.

30. Sumner Hall
    Sumner Hall is one of the last remaining African American Grand Army of the Republic halls in the country. It offers exhibits and programs on African American history.

31. Sultana Education Foundation
    The Sultana Education Foundation offers hands-on educational programs focused on the Chesapeake Bay. Take a sail on the historic schooner Sultana.

32. Historical Society of Kent County Museum
    This museum features exhibits on local history, including artifacts, photographs, and documents. It's a great place to learn about Chestertown's past.

Relaxing Retreats

Sometimes, you just need to relax and unwind. Chestertown offers several spots where you can do just that.

33. Inn at Huntingfield Creek
    This charming inn offers comfortable accommodations and beautiful grounds. It's a perfect place for a relaxing getaway.

34. Bridges Land Yoga
    Take a yoga class at Bridges Land Yoga to relax and rejuvenate. The studio offers a variety of classes for all skill levels.

Chestertown Awaits Your Adventure

Chestertown offers a mix of history, nature, and culture. Stroll through historic downtown with its charming shops and eateries. Visit the Chestertown Farmers Market for local produce and crafts. The Chester River is perfect for kayaking or a scenic boat ride. Don’t miss the Chestertown Tea Party Festival, a lively event celebrating colonial history.

For nature lovers, Eastern Neck National Wildlife Refuge provides trails and bird-watching opportunities. Washington College adds a youthful vibe with its events and performances. The Garfield Center for the Arts hosts plays and concerts, enriching the local culture.

Chestertown’s blend of activities ensures something for everyone. Whether you’re a history buff, outdoor enthusiast, or art lover, this town has it all. Pack your bags and get ready to explore all that Chestertown has to offer. Your adventure awaits!