12 Best Activities Near Chestertown Md

Nestled on the banks of the Chester River, Chestertown MD is a small but charming town that is rich in history and natural beauty. Whether you are a nature enthusiast, a history buff, a foodie or an art lover, there is something for everyone in this delightful town. From kayaking on the water to strolling through quaint streets lined with historic buildings, and from exploring local museums to indulging in fresh seafood, we have curated a list of the 12 best activities to do in and around Chestertown MD that will leave you with a lasting memory of your visit.

Kayaking on the Chester River

Chestertown, a charming town situated on the eastern shore of Maryland, is a perfect destination for outdoor lovers. The town's proximity to the Chester River offers an opportunity for kayakers to explore the river's serene beauty and wildlife. Kayaking on the Chester River is exciting, and there are many things you can do to make your experience even more enjoyable.

The first thing you need to do is find kayak rentals. Chesapeake Bay Outfitters and Chester River Kayak Adventures are two great local places that offer kayak rentals. They offer kayaks, paddles, and safety gear, and give you a brief lesson on paddling a kayak. They can also guide you and show you the best locations to kayak.

One of the best areas to kayak on the Chester River is the Eastern Neck National Wildlife Refuge. This area is home to many species of birds, including bald eagles, ospreys, and great blue herons. You can also see other wildlife, including deer, foxes, river otters, and muskrats. The water is calm, and the scenery is breathtaking.

Another area to explore is the Chestertown Marina. Paddle around the marina, check out the boats, and enjoy the views of the town from the water. You can also paddle up to Wilmer Park, a popular location for events and festivals.

If you're up for a more extended trip, kayak up to Queen Anne's Bridge, which sits on the border between Kent and Queen Anne's counties. The bridge is a famous landmark, and kayaking up to it is an adventure that you won't forget. Along the way, you'll see charming waterfront homes, farms, and beautiful landscapes.

Remember to wear appropriate clothing and check weather conditions before you go. It's also essential to bring water, sunscreen, and snacks to fuel your adventure. Be respectful of nature, do not disturb wildlife, and always leave no trace.

In conclusion, kayaking on the Chester River is a must-do activity near Chestertown, Maryland. It's a perfect way to enjoy nature, relax, and explore the beautiful scenery. There are many locations to kayak, depending on your skill level and preference. Rent a kayak and enjoy a fun and exciting adventure on the Chester River!

Visiting the Chestertown Farmers Market

Are you planning a visit to Chestertown, Maryland and looking for some fun things to do? Look no further than the Chestertown Farmers Market!

Located in the heart of Chestertown, the farmers market is open every Saturday from April to December. Here, you'll find a plethora of fresh and local produce, meats, cheeses, baked goods, and so much more! The market is a great place to stock up on delicious goodies for a picnic or to enjoy a tasty lunch from one of the many food vendors.

In addition to the amazing food offerings, the Chestertown Farmers Market also features artisanal crafts, jewelry, and other handmade items from local artisans and craftsmen. You never know what treasures you might find at the market!

But the Chestertown Farmers Market is more than just a place to shop and eat. It's also a hub of activity and community. The market often hosts live music and other events, making it a fun and engaging atmosphere for visitors and locals alike.

And if you're looking to learn more about the area and its history, the farmers market is just a stone's throw away from Chestertown's historic district. Take a leisurely stroll down High Street, explore the shops, and take a peek at some of the beautiful colonial-era homes and architecture.

So, whether you're a foodie looking for fresh produce and delicious treats or just looking for a fun and engaging way to experience Chestertown's vibrant community, be sure to add the Chestertown Farmers Market to your list of things to do near Chestertown, MD.

Touring the Schooner Sultana

If you're looking to explore the Chesapeake Bay region, one of the top things to do near Chestertown, MD, is to go on a sailing tour of the historic Schooner Sultana. This well-preserved replica of the original ship built in Boston in 1768 is a fantastic way to immerse yourself in history and experience the beauty of the Chesapeake Bay.

Built to be a replica of the original ship, the Schooner Sultana is a truly remarkable vessel. It boasts an impressive 118-feet length overall and a 24-foot beam, and its masts tower at an impressive 84 feet tall. The ship was designed in the tradition of 18th-century schooners used for transporting goods up and down the East Coast, and it is one of only a few remaining examples of these types of ships still in operation.

When you step aboard the Schooner Sultana, you'll be transported back in time to the age of sail. You'll be impressed by the unique craftsmanship of the ship, including the wooden hull, masts, and gunwales. You'll be awed by the evocative sailing experience as you sail the waters of the Chesapeake Bay, while listening to the sound of the sails as they catch the wind.

Of course, sailing on the Schooner Sultana is more than just a typical boat ride. On the ship, you'll also learn about the history of the region. The knowledgeable crew provides insight into the Chesapeake Bay's historic maritime traditions and the role the ship played in that history. The ship is also frequently used as a classroom, with educational programs for students of all ages, making it a great destination for families.

Another notable aspect of the Schooner Sultana is its eco-friendly design. The ship is powered by wind and solar energy, and its wastewater treatment system ensures that the Chesapeake Bay's delicate ecosystem remains preserved.

Overall, a tour of the Schooner Sultana is an essential part of any visit to Chestertown, MD. Whether you're a history buff, nature lover, or just looking for an exciting sailing experience, this impressive vessel has something for everyone. You can book tours of the Schooner Sultana online or in person at the Sultana Education Foundation, which is located on the Chestertown waterfront.

Hiking at Eastern Neck Wildlife Refuge

Are you looking for a fun outdoor activity near Chestertown, MD? Look no further than the Eastern Neck Wildlife Refuge where you can enjoy hiking and exploring the beautiful natural world around you.

Located just 15 minutes away from Chestertown, the Eastern Neck Wildlife Refuge is a haven for bird watchers, nature enthusiasts, and outdoor enthusiasts. Covering over 2,200 acres, this picturesque refuge is the perfect place to go for a scenic hike, bike ride, or picnic with family or friends.

One of the top activities to do at this refuge is hiking. There are a variety of different trails to choose from that range in length and difficulty, so you can find one that suits your needs and fitness level. Some of the popular trails include the Marsh Trail, Wildlife Trail, and the Bay View Trail. Each of these offers unique views and opportunities to explore the local flora and fauna.

Hiking the Marsh Trail allows you to get up close and personal with the tidal marshes and see a variety of bird species along the way. The trail is a little over a mile long and takes about 45 minutes to complete. It is a flat, well-maintained trail that is perfect for all skill levels.

If you're looking for a longer hike, consider the Wildlife Trail. This 1.5-mile loop trail is a bit more challenging, but offers stunning views of the meadows, woods, and tidal creeks. It is a great trail for spotting wildlife, including deer, red foxes, and various bird species.

For panoramic views of the Chesapeake Bay, take the Bay View Trail. This 1.2-mile trail is relatively easy and takes you to a scenic overlook where you can see the Bay and enjoy stunning vistas of the surrounding countryside.

Before setting off on a hike, be sure to grab a trail map and plenty of water. Additionally, be respectful of the wildlife and vegetation, travel on designated trails, and follow leave no trace principles.

In summary, the Eastern Neck Wildlife Refuge is a fantastic place to go hiking and enjoy the great outdoors. With a variety of trails to choose from, you're sure to find one that fits your needs and abilities. So, if you're looking for something fun to do near Chestertown, make sure to add this beautiful refuge to your list!

Biking the Chester River Trail

Chesertown, Maryland is a picturesque town nestled on the banks of the Chester River, offering a plethora of attractions to visitors and locals alike. One of the best ways to explore the town’s beauty is by taking a scenic bike ride on the Chester River Trail.

Stretching for 1.6 miles, the trail cuts across the heart of Chestertown, meandering through lush greenery, historic sites, and waterside scenery. The trail is paved, level, and offers a smooth ride for bikers of all levels.

The trail starts at the Wilmer Park and takes riders on a journey through the town’s historic district, where they can catch a glimpse of stunning architecture from the 1700s and 1800s. Along the way, bikers can stop by the Chestertown Marina, pick up a snack at one of the many cafes or restaurants, or admire the picturesque Church Hill Theatre.

As riders continue on the trail, they will cross over the scenic Chester River and get a glimpse of nature at its finest. The trail takes riders through the waterfront area, providing stunning views of the river, boats, and wildlife.

The Chestertown River Trail is not only a great choice for bikers but for walkers, joggers, and nature enthusiasts as well. There is plenty of space for everyone to enjoy the beautiful surroundings and watch the world go by.

Whether you are visiting Chestertown for the first time or a long-time resident, biking the Chester River Trail is a must-do activity. It is an excellent way to explore the town’s beauty, soak up the sun, and immerse yourself in nature. So rent a bike, grab a friend, and get ready for a scenic ride through the charming town of Chestertown.

Visiting the RiverArts Gallery

When you're in Chestertown, Maryland, there are plenty of activities to keep you busy and entertained! One of the must-visit places in this charming town is the RiverArts Gallery. Located in the heart of Chestertown, the gallery is a perfect spot to admire artwork and support local artists.

Upon visiting the gallery, you'll be greeted with a bright and welcoming space filled with stunning pieces of art. The gallery displays various types of artwork, including paintings, sculptures, jewelry, and more. There's something for everyone's taste and preference. You can spend hours walking through the gallery, admiring the art, and reading about the artists' inspirations.

Not only is the RiverArts Gallery an excellent spot for art enthusiasts, but it also offers various workshops and classes. Many artists teach classes at the gallery, covering a range of mediums, including painting, jewelry making, and pottery. You can take a class with an experienced artist and learn new techniques while creating your masterpiece.

Aside from the exhibitions and workshops, the RiverArts Gallery also hosts special events throughout the year. The gallery participates in the town's First Friday events, where visitors can enjoy live music, refreshments, and art exhibitions. RiverArts also often holds opening receptions for its monthly exhibitions.

The art at the RiverArts Gallery is constantly changing, meaning you can visit multiple times a year and still see something different each time. The gallery also offers pieces for sale, making it an excellent spot to purchase unique and one-of-a-kind artwork to bring back home.

In conclusion, visiting the RiverArts Gallery in Chestertown, Maryland, is an excellent way to experience and appreciate artwork while supporting local artists. The gallery's diverse exhibitions, workshops, and events make it a perfect destination for anyone, whether you're an art enthusiast or just looking for something fun to do in town.

Exploring downtown Chestertown

Chestertown, Maryland is a quaint town located in the heart of the eastern shore, offering visitors a charming array of historic buildings, boutique shops, and diverse dining options. If you're planning a visit to Chestertown, Maryland, exploring downtown should be at the top of your to-do list. Here are some of the must-do things when exploring downtown Chestertown:

Visit the Chestertown Farmers' Market

One of the best ways to immerse yourself in the town's community vibe is by visiting the Chestertown Farmers' Market, which runs every Saturday from April through December, from 9 am until noon. The market offers visitors fresh produce, meats, honey, and locally sourced crafts.

Tour the Historical Society of Kent County

The Historical Society of Kent County offers visitors a glimpse into the town's past. The society manages two museums, the Bordley History Center, and the Geddes Piper House. Both museums are located in the heart of Chestertown and feature relics from the 18th and 19th centuries.

Stroll Along the Chester River Walk

The Chester River Walk is a two-mile scenic path that winds along the Chester River. Visitors can enjoy a leisurely stroll, take in the natural beauty of the river, and even spot some wildlife. The river walk is an excellent place to take a break, relax, and take in the views.

Shop at Local Boutiques

Downtown Chestertown offers a myriad of local boutiques and shops. From jewelry to clothing to artisanal goods, you're bound to find something unique and special. Be sure to visit Twigs and Teacups, a charming boutique known for its handmade pottery, or Sultana Downrigging, which features nautical-inspired goods.

Grab a Bite to Eat

Downtown Chestertown offers an array of dining options ranging from cozy cafes to upscale restaurants. If you're looking for a quick bite, visit Evergrain Bread Company, which has fantastic sandwiches and freshly baked bread. For an upscale dining experience, visit Procolino's Italian Restaurant, known for its homemade pasta and seafood dishes.

In conclusion, exploring downtown Chestertown is a perfect way to spend a day or even a weekend exploring the eastern shore. With its rich history, unique shopping destinations, and diverse dining options, Chestertown offers a little something for everyone. So, be sure to add this charming town to your list of must-see destinations.

Wine tasting at Crow Vineyard & Winery

If you're looking for a fun and memorable activity to do near Chestertown, Maryland, why not consider a wine tasting at Crow Vineyard & Winery? This beautiful winery and farm is located just 10 minutes away from downtown Chestertown and offers a unique wine tasting experience that's perfect for groups or individuals.

Crow Vineyard & Winery is a family-owned and operated business that has been producing high-quality wines since 2012. They have a wide variety of wines to choose from including reds, whites, roses, and sparkling wines. Some of their most popular wines include the Barbera, Chardonnay, and the sparkling Albarino.

One of the best things about visiting Crow Vineyard & Winery is the beautiful scenery. The winery is located on a 365-acre farm that has been in the Crow family for several generations. The farm is a picturesque setting with rolling hills, lush green fields, and a beautiful vineyard where the grapes are grown. You can take a stroll around the vineyard and enjoy the beautiful surroundings while sipping on your favorite wine.

In addition to their delicious wines and stunning scenery, Crow Vineyard & Winery also offers a variety of experiences and events. They frequently host live music events, vineyard tours, and private tastings for groups. If you're looking for a fun and unique bachelorette or birthday party idea, they also offer private party packages.

If you're new to wine tasting, the staff at Crow Vineyard & Winery is always happy to share their knowledge and expertise with you. They will guide you through the tasting process, explain the different flavors and notes in each wine, and provide recommendations based on your personal preferences.

In conclusion, there's no better way to spend a day near Chestertown, Maryland than by visiting Crow Vineyard & Winery. Whether you're a wine lover or just looking for a fun activity to do with friends, this beautiful winery offers something for everyone. So grab your friends and head over to Crow Vineyard & Winery for a day of wine tasting and relaxation.

Fishing on the Chester River

Chestertown is a charming town in Maryland and is located near the Chester River, which offers many exciting activities such as fishing. If you are someone who loves fishing, you will be delighted to know that the Chester River provides a wide variety of fish species, making it a popular destination for anglers. Here are some things you need to know about fishing on the Chester River.

First, it is essential to get your Maryland fishing license. Licenses are available for visitors from out of state, and they can be easily obtained online or from a local sporting goods store. With your license in hand, you are free to fish on the Chester River.

The Chester River offers many opportunities to fish for a variety of species, including striped bass, bluefish, croaker, and white perch, among others. You can fish from the river's shore or rent a boat and fish from the water. The river has several public boat ramps, so launching your boat should not be a problem.

If you are an inexperienced angler, you can hire a guide to help you navigate the River and show you some of the best spots to fish. A knowledgeable guide will help you catch more fish and make your experience more enjoyable. They will know how and where to find the species you are targeting, and they will also have all the necessary equipment.

When planning your fishing trip, it is also essential to keep in mind the best time to fish on the Chester River. The fishing season runs from late spring to early fall, with the peak season being between late June and mid-September. During this period, you can expect to catch the most fish since they are most active during the warmer months.

In conclusion, if you are looking for an excellent fishing destination, the Chester River is an excellent place to visit. Whether you prefer to fish from the shore or the water, you will find plenty of opportunities to catch a variety of species. Be sure to obtain your fishing license, hire a guide, and plan your trip according to the best season. With these considerations, you are sure to have a memorable fishing experience on the Chester River.

Taking a scenic drive through the Eastern Shore countryside

Nestled in the heart of Eastern Shore, Chestertown is a charming town known for its historic architecture, cultural events, and scenic landscapes. If you are looking for a fun and relaxing activity near Chestertown, why not take a scenic drive through the breathtaking countryside? Here are some of the things you can see and do along the way.

Start your adventure by heading east of Chestertown towards the Maryland Route 20, also known as the Rock Hall Road. This road will take you through miles of idyllic farmland, vineyards, and waterways, offering plenty of opportunities to enjoy the natural beauty of the area. Be sure to roll down your window and breathe in the fresh air as you marvel at the peacefulness of the countryside.

As you drive further down the road, you will come across the charming fishing village of Rock Hall, famous for its beautiful marinas, seafood restaurants, and quaint shops. Take a stroll along the waterfront and watch the boats go by. If you're feeling adventurous, book a fishing or kayaking trip and explore the Chesapeake Bay up close.

From Rock Hall, continue your scenic drive towards the picturesque town of Chestertown, where you can enjoy a variety of cultural attractions, excellent dining options, and charming boutiques. Take a stroll along the riverfront promenade and admire the colonial-era architecture of the town. If you're a history buff, don't miss the chance to visit the Chestertown Tea Party Ships and Museum and learn about the town's role in the American Revolution.

Another must-see attraction near Chestertown is the Eastern Neck Wildlife Refuge, a 2,285-acre sanctuary that provides a habitat for over 240 species of birds, as well as deer, foxes, and other wildlife. Take a leisurely hike through the scenic trails, birdwatch from the observation platforms, or join a guided tour to learn more about the ecology and conservation efforts of the area.

If you're visiting Chestertown during the fall season, you can't miss the opportunity to go apple or pumpkin picking at one of the many local orchards. Sip on hot apple cider and savor a freshly baked apple pie while enjoying the beautiful colors of the surrounding scenery.

In summary, taking a scenic drive through the Eastern Shore countryside is a fantastic way to explore the beauty and richness of Chestertown's surroundings. Whether you're looking for outdoor adventures, cultural experiences, or simply a peaceful escape from the city, there's something for everyone along the way. So what are you waiting for? Grab your keys, hit the road, and get ready for an unforgettable journey!

Visiting the Wilmer Park Fountain

Chestertown, Maryland is a charming small town that is rich in history, culture, and scenic beauty. If you are looking for things to do near Chestertown, a visit to the Wilmer Park Fountain is a good place to start. The Wilmer Park Fountain is a beautiful landmark in Chestertown that is a popular destination for tourists and locals alike.

The fountain in Wilmer Park is a stunning work of art that sits in the center of the park. It was built in 1929 and was dedicated to Dr. Isaac Winchester, who was a physician and philanthropist in Chestertown. The fountain is surrounded by lush greenery and trees, which makes it a perfect spot for a relaxing picnic or a quiet walk.

The Wilmer Park Fountain is a great place to take pictures, especially during sunset when the golden light casts beautiful reflections on the fountain. You can also bring your own picnic basket and enjoy a meal in the park. The park is an ideal spot for families with children as they can run around and play on the grass while you sit back and relax.

The park also hosts many events throughout the year, including concerts, festivals, and weddings. If you're visiting Chestertown during the summer, don't miss the Fourth of July fireworks display that is held in Wilmer Park. The display is a favorite among locals and visitors alike.

During your visit to the Wilmer Park Fountain, take a leisurely stroll around the park to explore its many delights. The park has many historical markers that describe the area's significance throughout history. You can also take a walk along the Chester River, which borders the park.

In conclusion, a visit to the Wilmer Park Fountain is a must-do if you're in Chestertown, Maryland. It's a beautiful and historic site that is perfect for a relaxing day out with your family and friends. So, don't miss this wonderful opportunity to experience the natural beauty of the Eastern Shore of Maryland.

Checking out the Chestertown Tea Party Festival (seasonal)

Chestertown, Maryland is a charming and historic town located on the eastern shore of the Chesapeake Bay. Visitors to the area will find plenty of things to do and see, from touring the town's many historic sites to enjoying outdoor activities along the waterfront. One of the most popular events in the area is the annual Chestertown Tea Party Festival, which takes place each spring.

The Chestertown Tea Party Festival is a celebration of the town's colonial history and its role in the American Revolution. The festival takes place over the course of a weekend and includes a wide range of events and activities for visitors of all ages. Some of the highlights of the festival include:

• The reenactment of the famous Boston Tea Party, which is performed by a group of local actors in period costumes. Visitors can watch as they dump crates of "tea" into the Chester River to protest British taxation.
• Live music and entertainment throughout the weekend, including a parade, colonial-era games, and historical demonstrations.
• A variety of food and craft vendors selling everything from fresh seafood to handmade jewelry.
• Historical tours of Chestertown and its many historic buildings, including the Geddes-Piper House, the Elwood House, and the Shrewsbury-Windle House.

Overall, the Chestertown Tea Party Festival is a great way to experience the history and culture of this charming Maryland town. Whether you're a history buff, a foodie, or just looking for a fun weekend getaway, there's something for everyone at this annual event. So mark your calendar and get ready to experience all that Chestertown has to offer!

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