12 Fun Things To Do In Chestertown, Md

things to do chestertown md

If you're looking for an exciting and unique getaway, look no further than Chestertown, Maryland! Located on the banks of the Chester River, this charming town offers a variety of activities designed to delight and entertain. From outdoor adventures in the nearby parks to culture-filled experiences at the historic sites and museums, there are 12 fun things to do in Chestertown that are sure to keep you coming back for more. From kayaking and strolling down the riverwalk to exploring the colonial-era architecture and enjoying the local cuisine, Chestertown is a destination that is sure to please.

Characteristic Tips
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Transportation Rent a car or use Uber
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Food & Beverage Visit local restaurants

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Take a Tour of Historic Sotterley Plantation

Sotterley Plantation in Chestertown, Maryland, is a National Historic Landmark and offers a unique glimpse into colonial life and the history of plantations in Maryland. Built in 1703 by the Sotterley family, the Plantation is one of the oldest surviving tobacco plantations in the United States and the only one still open to the public.

Visitors to the Plantation can take a guided tour of the manor house, the outbuildings, the grounds, and the gardens, as well as explore the adjacent Maryland Historical Society Museum and the Sotterley Plantation Visitor’s Center. Along the tour, visitors will learn about the Sotterley family, the history of tobacco farming, and the African-American experience in Maryland. The tour also includes a visit to the kitchen, which was the center of activity for the house, as well as the slave quarters, which are a testament to the harsh realities of life on a plantation.

The Plantation also offers a variety of special events throughout the year, including the Sotterley Storytelling Festival, which brings together storytellers from all over the country to tell stories about Maryland’s history and culture. The Festival also features music, living history demonstrations, and a variety of food vendors.

The Plantation also offers educational programs for students of all ages. Visitors can learn how to make soap from lard, or how to make a quilt from scraps of fabric. They can also learn about plantation life and the importance of preserving the Plantation’s history.

The Plantation is open to the public year-round and offers a variety of activities and events. Visitors can take a tour of the manor house and outbuildings, explore the grounds and gardens, or attend one of the many special events. The Plantation is a unique opportunity to explore the history of Maryland and its plantations, and to learn about the hardships faced by its early settlers.

“Sotterley is a remarkable place,” says Plantation Director, David Young. “It’s a living history lesson that allows visitors to explore how early settlers lived, worked, and interacted with the land and its people.”

The Sotterley Plantation is a great place to explore Maryland’s colonial history and to learn about the importance of preserving the past. With its special events and educational programs, the Plantation provides a unique opportunity to explore the history of the Chesapeake region and its people.

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Visit the Chestertown Tea Party Museum

The Chestertown Tea Party Museum is a must-see destination for anyone visiting the historic town of Chestertown, Maryland. Located in the heart of the town, the museum celebrates the town’s rich history and the legacy of the original Tea Party of 1774. The museum offers visitors an opportunity to explore the history of the Tea Party, the Revolutionary War and the town of Chestertown itself.

Visitors to the museum can take a guided tour, which brings the past to life with stories and anecdotes about the people and events that shaped Chestertown. The tour includes demonstrations of the tea-making process, a visit to the Tea Shop, and a chance to sample the famous “Chestertown Tea”. At the end of the tour, visitors can purchase the tea to take home as a souvenir.

The museum also offers a variety of interactive displays and exhibits, including a re-creation of a Revolutionary War-era print shop, an interactive map of Chestertown and a “tea house” where visitors can learn about the various types of tea and how to brew it. In addition, visitors can learn about the history of the Chestertown Tea Party, and hear about the brave men and women who risked their lives to stand up for their beliefs.

For those who want to extend their visit, the museum also offers a variety of special events and programs, including lectures, film screenings, and music performances. In addition, the museum offers educational programs for students, from elementary school to college, featuring hands-on activities and interactive exhibits.

The Chestertown Tea Party Museum is open year-round, but summer months are especially popular for visitors. The museum is located at the intersection of High Street and Queen Anne’s Avenue and is open Tuesday through Sunday from 10 am to 4 pm. Admission is free, and there is plenty of parking nearby.

The Chestertown Tea Party Museum is a great way to learn more about the history of Chestertown and the Revolutionary War. Visitors can take a guided tour, explore interactive exhibits and enjoy a variety of special events and programs. Whether you’re a history buff or just looking for a fun day out, the Chestertown Tea Party Museum is the perfect place to visit.

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Explore Washington College

Washington College, located in Chestertown, Maryland, is a private liberal arts college with a long and storied history. Founded in 1782, it is the tenth oldest college in the United States and the first chartered college in America. It is also the only college in the country that is named after George Washington, who was its first benefactor.

The college is situated in the beautiful town of Chestertown, which is located on the Eastern Shore of Maryland. The town is steeped in history and its streets are lined with historic buildings. The college itself is home to numerous historic buildings including the William Smith Hall and the Hodson Hall, both of which are National Historic Landmarks.

Washington College offers a variety of activities for visitors to enjoy. The college has a Museum of Fine Arts, which showcases a variety of artworks from local, regional, and international artists. There are also several galleries featuring artwork from students and faculty. Visitors can also enjoy the college’s outdoor amphitheatre, which offers a variety of performances throughout the year.

For those looking for outdoor activities, there are plenty of options. Chestertown is home to several parks and trails, including the Gunpowder River Trail and the Chesapeake Bay Maritime Museum. Visitors can also enjoy boat tours, fishing, kayaking, and other water activities at the nearby Chester River.

The college also hosts a number of events throughout the year. These include a summer music festival, a harvest festival, and a variety of other arts and cultural events. Visitors can also take part in the college’s weekly lectures, which are open to the public.

Washington College is also home to a number of shops, restaurants, and other attractions. Visitors can find a wide range of merchandise at the college’s bookstore, and can dine at any of the local restaurants. The college also hosts a farmers’ market on the weekends, where visitors can purchase locally grown produce and other goods.

Visiting Washington College is a great way to explore the history and culture of Chestertown and the Eastern Shore. Whether you’re looking for outdoor activities, cultural events, or shopping, Washington College has it all. So come and explore all that the college has to offer, and don’t forget to bring your camera!

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Enjoy the Great Outdoors at Wilmer Park

Wilmer Park in Chestertown, Maryland is the perfect place for anyone looking to enjoy the great outdoors. With over 450 acres of land, visitors can explore the miles of wooded trails, enjoy the scenic vistas of the Chester River, and even cast a line in the park's many fishing spots. From bird-watching to kayaking, Wilmer Park has something for everyone.

For those who want to take in the park's natural beauty, Wilmer Park is filled with a variety of wildlife, including deer, foxes, and turtles. Bird-watchers will love the variety of species that make their home in the park, including cardinals, blue jays, and even bald eagles. For a more adventurous experience, visitors can explore the park's many trails, which range from easy to challenging. Whether you're looking for a leisurely stroll or a more strenuous hike, Wilmer Park has something for everyone.

If you're looking for a more active experience, Wilmer Park also offers plenty of activities to keep you busy. Kayaking is one of the most popular activities in the park, as the Chester River provides the perfect backdrop for a leisurely paddle. Fishing is also a popular activity, with plenty of spots for anglers to cast their lines. And for those who want to relax, the park also offers picnic areas and pavilions, perfect for a family outing or just a day of relaxation.

But Wilmer Park isn't just about outdoor activities. The park also offers cultural experiences, such as the Wilmer Park Music Series, which features a variety of musical acts throughout the summer. The park also hosts a variety of events throughout the year, including the Chestertown Arts and Crafts Festival, the Chestertown Farmers' Market, and the Annual Chestertown Festival.

No matter what time of year you visit Wilmer Park, there's always something to do. From outdoor activities to cultural events, Wilmer Park has something for everyone. So come explore the great outdoors and enjoy the beauty of Wilmer Park. It's the perfect place to relax, explore, and enjoy the great outdoors.

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Kayak the Chester River

Chester River, located in Chestertown, Maryland, is a beautiful destination for kayaking and other outdoor activities. Whether you’re an experienced kayaker looking for a great adventure, or a beginner looking to learn the basics of the sport, this unique and scenic river is worth a visit.

The Chester River is a great kayaking spot for all levels of experience. Beginners will appreciate the calm, wide waters and lack of strong currents, while more experienced kayakers will find plenty of opportunities to explore the river’s many coves and inlets. Wildlife is plentiful in the area, making it an ideal destination for photographers, birdwatchers, and nature lovers.

The best time to kayak the Chester River is during the summer months, when the water is warm and the current is mild. The river is also accessible in the fall, but the water can be too cold for some kayakers. Spring is a great time to kayak the river, as the days are longer and the wildlife is more active.

When kayaking the Chester River, it’s important to be aware of the wildlife in the area. Bald eagles, ospreys, and great blue herons are just a few of the birds that make their home in the river. Keep an eye out for seals, as well, which are often spotted in the area.

It’s also important to be aware of the river’s changing tides. The tide in the Chester River can be unpredictable, and can change drastically in a very short period of time. Be sure to plan your kayaking trip around the tide schedule to avoid any surprises.

If you’re looking for a unique and unforgettable experience, kayaking the Chester River is a great option. With its tranquil waters and abundance of wildlife, this beautiful river is sure to provide a memorable kayaking adventure. Whether you’re a beginner or a seasoned kayaker, the Chester River has something to offer everyone.

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Relax at Rock Hall Beach

Rock Hall Beach in Chestertown, Maryland is a hidden gem on the Eastern Shore. With its white sand, crystal clear waters and breathtaking views of the Chesapeake Bay, it is the perfect destination for a relaxing getaway.

This secluded beach is located on the north end of Kent Island and is only accessible by boat. For those who don’t have access to a boat, there are boat rentals available in nearby towns. Once you arrive at the beach, you will be greeted with a beautiful view of the bay as well as plenty of opportunities for swimming, fishing and sunbathing.

The waters at Rock Hall Beach are shallow and warm, making them ideal for swimming and wading. If you plan on fishing, the beach is a great spot to cast your line and catch some bluefish, flounder, and rockfish. For those who just want to take in the scenery, the beach offers stunning views of the bay and plenty of spots to relax and soak up the sun.

For those looking to explore more of the area, there are plenty of options. There are several marinas in the area where you can rent a boat or go on a fishing charter. In addition, you can take a scenic drive down the Eastern Shore and explore small towns like St. Michaels and Cambridge.

No matter what you’re looking for in a beach getaway, Rock Hall Beach in Chestertown, Maryland is sure to provide a relaxing, memorable experience. From swimming and fishing to simply taking in the views, this beach is the perfect spot to get away from it all. So if you’re looking for a tranquil spot to kick back and relax, look no further than Rock Hall Beach.

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Dine at the Schooner's Wharf

The Schooner’s Wharf of Things to Do in Chestertown, Maryland, is a must-visit destination when exploring the town. This waterfront restaurant offers some of the best seafood in the area, along with stunning views of the bay. Whether you’re looking for a romantic evening out or a family-friendly meal, Schooner’s Wharf is the place to go.

Dining at Schooner’s Wharf is an experience unlike any other. The menu includes classics like crab cakes and oysters, but also more unique items like mussels, fried green tomatoes, and even a vegan black bean burger. With outdoor seating and an indoor dining room with floor to ceiling windows, guests can take in the stunning views of the bay while they eat.

The atmosphere at Schooner’s Wharf is relaxed and friendly. The restaurant is family-owned and operated, and the staff are always ready to answer questions and help with orders. The restaurant has been in business since the late 1800s, and the walls are adorned with vintage photos and artifacts, giving the restaurant a unique, old-fashioned charm.

The Schooner’s Wharf is also a great spot to grab a drink. The bar serves a variety of craft beers, wines, and cocktails. The signature drink, the Schooner’s Wharf Margarita, is a must-try.

In addition to dining and drinks, Schooner’s Wharf also offers live music. The restaurant hosts a variety of music acts from Thursday to Sunday, including jazz, blues, and more.

If you’re looking for a unique experience in Chestertown, you won’t want to miss out on Schooner’s Wharf. Known as the “Pearl of the Eastern Shore,” this waterfront restaurant is the perfect spot for a romantic date night or a fun evening out with family and friends. So grab a seat and get ready to enjoy the best seafood in town, with some of the best views around.

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Check Out the Chestertown Farmer's Market

Chestertown Farmer's Market is a vibrant gathering of local farmers and vendors from around the area. Located in the heart of Chestertown, Maryland, the market offers a variety of fresh fruits and vegetables, meats, seafood, baked goods, and artisanal crafts. Open from April through November, the market is a great place to find fresh, locally grown produce, as well as unique handmade items.

The Chestertown Farmer's Market is a great way to experience the local culture and meet the people who grow and craft the items. Every Saturday morning, the market is filled with cheerful vendors, excited shoppers, and a wide variety of products. The atmosphere of the market is friendly and welcoming, and it's a great way to get to know the community.

When it comes to shopping at the Chestertown Farmer's Market, there are a few tips to keep in mind. First, bring reusable bags and a cooler to keep your produce and other items fresh. Second, bring cash, as many vendors do not accept credit cards. Finally, be sure to arrive early, as some of the best items sell quickly.

In addition to the market, Chestertown offers a variety of activities, from outdoor recreation to arts and culture. From hiking, biking, and kayaking, to visiting the historic downtown area, there is something for everyone. The town also boasts a variety of restaurants, ranging from casual to upscale, as well as charming shops and galleries.

For those looking for a unique experience, the Chestertown Farmer's Market offers a variety of cooking classes and tasting events. From pickling and canning to salsa making, these classes are a great way to learn about local cuisine and the art of preserving. Visitors can also participate in a number of workshops, seminars, and lectures on topics such as sustainable farming and gardening, food preservation, and sustainable living.

The Chestertown Farmer's Market is a great way to experience the local culture and meet the people who grow and craft the items. Whether you're looking for fresh produce, unique handmade items, or a unique experience, the Chestertown Farmer's Market has something for everyone. Open from April through November, the market is located at the intersection of South Cross Street and High Street in Chestertown, Maryland.

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Take a Walk Along the Waterfront

Chestertown, Maryland is a charming waterfront town located on the Eastern Shore of the Chesapeake Bay. With its beautiful scenery, bustling downtown, and plenty of activities and attractions, Chestertown is the perfect place to spend the day. If you’re looking for a unique and enjoyable way to explore this quaint town, then a walk along the waterfront may be just the ticket.

A waterfront walk in Chestertown is a delightful experience. Start your journey at the Chester River Bridge, where you’ll find a spectacular view of the river and the surrounding area. From here, you can stroll along the boardwalk, taking in the sights and sounds of the waterfront. You’ll pass by the historic Wilmer Park, where you can take a break and enjoy the lush greenery.

Continue your journey along the waterfront and you’ll come across a variety of attractions. Stop at the Chestertown Marina, where you can rent kayaks and paddleboards or take a scenic boat tour. Make sure to take a break at Wilmer Park Beach, where you can soak up some sun and relax on the sandy shore.

When exploring the waterfront in Chestertown, don’t forget to stop at the Chestertown Tea Party Museum. This museum is dedicated to the history of the famous Tea Party, which was held in Chestertown in 1774. Here, you’ll learn about the event that helped spark the Revolutionary War.

After taking a walk along the waterfront, be sure to check out some of Chestertown’s other attractions. There are plenty of historical sites to explore, such as the Kent County Courthouse, the oldest courthouse in Maryland. Or, if you’re in the mood for some shopping, make your way to the Washington College campus, where you’ll find a variety of unique stores and boutiques.

No matter what your interests, a walk along the waterfront of Chestertown is sure to be an enjoyable experience. With its picturesque views, historic sites, and plenty of activities to choose from, Chestertown is the perfect place to spend the day. So grab your walking shoes and get ready to explore the Chesapeake Bay’s most charming waterfront town.

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Catch a Show at the Garfield Center for the Arts

The Garfield Center for the Arts in Chestertown, MD is one of the premier venues for entertainment in the area. Located on the banks of the Chester River, the Garfield Center is a state-of-the-art facility with a focus on performing arts. It is home to theatrical productions, music concerts, dance performances, and more. With a variety of programming and events throughout the year, the Garfield Center is an ideal destination for those looking for an exciting and memorable experience.

The Garfield Center has a wide array of performances to choose from, ranging from local and regional talent to international acts. There are shows for all different ages, from family-friendly to more adult-oriented productions. Whether you’re looking for a comedy show, a musical, or a dance performance, the Garfield Center has something to offer.

A great feature of the Garfield Center is its accessibility. The facility is conveniently located in downtown Chestertown and is easily accessible by car or public transport. Additionally, there are plenty of parking options available, making it easy to get to the theater.

Visitors to the Garfield Center can also take advantage of the many amenities offered. The theater has a full-service bar and concession stand, as well as pre-show dining options. Additionally, the facility has a gift shop, where visitors can pick up souvenirs and memorabilia.

If you’re looking for a unique and exciting experience, then catching a show at the Garfield Center is a must. Whether you’re a local or a visitor to Chestertown, MD, the Garfield Center is sure to provide an unforgettable experience. With its convenient location and wide variety of programming, the Garfield Center is the perfect place to catch a show.

For those looking for a more intimate experience, the Garfield Center also offers smaller, more intimate shows. These include cabaret performances, musicals, and other theatrical events. These shows provide a more intimate atmosphere, allowing for a more personal connection with the performers.

Whether you’re looking for a night out with friends or a romantic evening for two, the Garfield Center is sure to provide an unforgettable experience. With its convenient location and wide variety of programming, the Garfield Center is the perfect destination for those looking for a unique and memorable experience.

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Shop the Boutiques of High Street

High Street of Chestertown, Maryland is a great place to shop for unique finds. Whether you're looking for a special gift or just browsing, the diverse array of boutiques and shops is sure to have something for everyone.

The High Street area is known for its quaint and charming atmosphere, making it an ideal spot for a leisurely shopping experience. Located in the historic downtown area, the street is lined with charming brick buildings, cobblestone sidewalks and colorful awnings.

If you're looking for unique jewelry, home décor, clothing and more, you'll find plenty of options on High Street. From vintage clothing stores to trendy boutiques, there's something for everyone. You'll also find plenty of specialty shops, such as a guitar store, a gourmet popcorn shop, and a toy store.

And if you're looking for a bite to eat, High Street has plenty of restaurants to choose from. Whether you're in the mood for a casual lunch or a romantic dinner, you'll find something to suit your tastes.

But it's not just boutiques and restaurants that make High Street so special. During the summer months, the street is home to a number of festivals and events, such as the Chestertown Tea Party Festival and the Chestertown Jazz Festival. These events draw large crowds and provide a great opportunity to explore the area's culture and history.

High Street is also home to a number of popular attractions, including the Chester River Museum and the Chester River Maritime Museum. Both museums offer visitors a chance to learn more about the area's rich history and culture.

If you're looking for a unique shopping experience, the boutiques and shops of High Street of Chestertown, Maryland are sure to have something for you. Whether you're looking for a one-of-a-kind piece of jewelry or a special gift, you're sure to find it here. From boutique shopping to dining and attractions, High Street has something for everyone.

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Enjoy a Scenic Drive Along the Eastern Neck National Wildlife Refuge

The Eastern Neck National Wildlife Refuge is an amazing destination located in Chestertown, Maryland. Here, you can experience some of the most beautiful and stunning views of the Chesapeake Bay. This refuge is home to various species of wildlife and vegetation, making it the perfect spot for a scenic drive.

A great way to enjoy a scenic drive along the Eastern Neck National Wildlife Refuge is to head out early in the morning. The sun will be just rising over the horizon, illuminating the landscape with its warm, golden hue. The tranquil atmosphere of this refuge will be sure to mesmerize you. As you drive along, you'll be able to see many different types of birds and other wildlife, up close. This is a great opportunity to observe the natural beauty of the area.

When you decide to take a scenic drive along the Eastern Neck National Wildlife Refuge, make sure to bring a camera with you. This is a great chance to capture some amazing photographs of the different species of wildlife and scenery. You can also bring a pair of binoculars, so you can get a better view of the birds, animals, and plants in the area.

Another great option while you're here is to take a boat tour of the refuge. This will give you a chance to get a truly up-close and personal view of the wildlife and vegetation that make this refuge so special. There are several companies that offer boat tours of the refuge, so you should be able to find one that fits your budget and interests.

The Eastern Neck National Wildlife Refuge is a great place to spend the day. Whether you're just taking a scenic drive or going on a boat tour, there are plenty of things to do in Chestertown, Maryland. This refuge is the perfect spot to get away from the hustle and bustle of everyday life and to reconnect with nature.

For a truly unique experience, why not take a kayaking tour of the refuge? This is a great way to explore the area from a different perspective. You'll get to paddle through the different areas of the refuge, taking in the sights and sounds of nature.

Finally, if you'd like to learn more about the Eastern Neck National Wildlife Refuge, be sure to check out the visitor center. Here, you can find information about the history of the refuge, as well as the different species of wildlife that call the refuge home. You can also pick up some souvenirs to remember your visit.

The Eastern Neck National Wildlife Refuge is a great place to spend an afternoon or weekend. Whether you're looking for a scenic drive or a chance to get up close and personal with nature, you'll be sure to find something to love in Chestertown, Maryland.

Frequently asked questions

Popular attractions in Chestertown include the historic district, the Chester River, the Washington College campus, the Garfield Center for the Arts, and the Chestertown Tea Party Museum.

Yes, Chestertown hosts several events throughout the year, including the Chestertown Tea Party Festival, the River Arts Festival, and the Chestertown Jazz Festival.

There are several restaurants in Chestertown, including the Imperial Hotel, the Fish Whistle, the Brick Salt, and the Taproom at the Imperial.

Chestertown offers a variety of outdoor activities, such as fishing, kayaking, boating, and hiking. There are also several parks and trails in the area.

Chestertown has several cultural activities, including the Garfield Center for the Arts, which offers theater, dance, and music performances. There are also several galleries and museums in the area.

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3 Comments

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Rahul Green

Last weekend, my family decided to take a day trip to Chestertown, MD and we were pleasantly surprised by the variety of things to do in this small town. We started our day by exploring the historic district and marveling at the well-preserved Georgian, Federal, and Victorian architecture. Next, we visited Washington College, the country's 10th oldest liberal arts college, and took a leisurely walk through the beautiful campus. For lunch, we opted for a picnic by the river and enjoyed the peaceful ambiance. To end our visit, we stopped by some of the local boutiques and shops, where we found unique souvenirs to take home. Chestertown is definitely a hidden gem worth exploring!
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May Hart

I recently visited Chestertown, MD and had an amazing time exploring all the things to do in this charming town. One of my favorite activities was taking a stroll along the waterfront and admiring the beautiful views of the Chester River. I also loved checking out the local art scene, with galleries showcasing the works of talented artists from the area. And of course, I couldn't miss out on tasting some delicious Maryland seafood at one of the waterfront restaurants. Chestertown truly has something for everyone, and I can't wait to go back and discover more!
Thank you so much for sharing your experience in Chestertown, MD. I'm thrilled to hear that you had such a wonderful time exploring this charming town. The waterfront sounds absolutely stunning, and I can imagine how peaceful and picturesque it must be to take a stroll along the river. Discovering the local art scene sounds like such a treat, and I'm glad you got to see the works of talented artists from the area. And of course, indulging in some delicious Maryland seafood is always a must! It sounds like you truly had an amazing time, and I hope you have the opportunity to go back and discover even more of what Chestertown has to offer.

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