Chestertown Travel Guide

Explore the charming town of Chestertown in Maryland with our comprehensive travel guide. Discover the best places to visit, things to do, where to stay, and more.


Introduction to Chestertown

Located in the picturesque Eastern Shore region of Maryland, Chestertown is a peaceful waterfront town that offers an abundance of history, culture, and scenic beauty. Founded in 1706, this charming town is steeped in American history and is home to some of the most well-preserved colonial architecture in the country. Chestertown is also renowned for its vibrant arts scene, specialty shops, and numerous outdoor recreational opportunities.

In this comprehensive travel guide, we’ll provide you with all the information you’ll need to plan a fun-filled and memorable trip to Chestertown.

List of Places to Visit in Chestertown

Whether you’re a history buff, an art enthusiast, or a nature lover, Chestertown has something to offer for everyone. Here are some of the must-visit places in the town:

Culturally Important Attractions: Museums and Historical Places

  • The Chestertown Historic District: Take a stroll through the heart of the town’s historic district and admire the beautiful colonial buildings that have been lovingly restored to their former glory.
  • The Historical Society of Kent County: Discover the rich history of Kent County and explore exhibits on maritime history, agriculture, and the Civil War.
  • Sultana Education Foundation: Learn about the town’s maritime heritage and ecology at this waterfront educational center. Take a sunset sail on the historic tall ship Sultana.

Natural Attractions of Chestertown: Outdoor Adventures and Scenic Views

  • Eastern Neck National Wildlife Refuge: Explore the miles of scenic trails within the refuge and enjoy birdwatching, picnicking, and hiking.
  • Wilmer Park: Stroll along the riverwalk at this picturesque waterfront park. Enjoy stunning views of the Chester River and the town’s marina.
  • Chestertown Farmers’ Market: Visit the town’s weekly farmers’ market and stock up on fresh produce, baked goods, and artisanal products.

Hiking/Biking Routes of Chestertown

Chestertown is a haven for outdoor enthusiasts, with plenty of hiking and biking trails that allow visitors to explore the town’s natural beauty. Here are some popular routes:

  • The Chestertown River Walk Trail: This one-mile trail winds through the town’s historic district, providing stunning views of the Chester River and the town’s marina.
  • Eastern Neck Island Loop Trail: This five-mile trail takes hikers through the heart of Eastern Neck National Wildlife Refuge. Enjoy birdwatching and wildlife sightings along the way.
  • The Hopkins Game Creek Trail: This four-mile trail is perfect for mountain bikers, with technical terrain and challenging climbs.

Best Things to Do in Chestertown: Activities and Tours

In addition to exploring the town’s museums, historical landmarks, and natural attractions, Chestertown also offers a variety of exciting activities and tours. Here are some options:

  • Sailing Tours: Take a sunset sail on the historic tall ship Sultana or enjoy a private sailing charter.
  • Kayaking and Canoeing: Paddle down the town’s scenic rivers and waterways with local outfitters or rent kayaks and canoes for a self-guided adventure.
  • Arts and Culture: Visit the town’s galleries and studios and attend live performances and concerts at local venues.

Week-Long Itinerary for Chestertown

A week in Chestertown will give you ample time to experience all that this charming town has to offer. Here’s our suggested itinerary:

Day 1: Arrive in Chestertown and explore the town’s historic district. Visit the Chestertown River Walk Trail, Eastern Neck National Wildlife Refuge, and the Wilmer Park.

Day 2: Take a sailing tour on the tall ship Sultana and learn about the town’s maritime history. Visit the Historical Society of Kent County and the Sultana Education Foundation.

Day 3: Rent bikes and explore the Hopkins Game Creek Trail. Visit the town’s galleries and studios and attend a live performance at the Garfield Center for the Arts.

Day 4: Visit the Chestertown Farmers’ Market and stock up on fresh produce and artisanal products. Take a kayaking tour on the Chester River.

Day 5: Visit the Chestertown Tea Party Museum and learn about the town’s role in the American Revolution. Take a historical walking tour of the town.

Day 6: Visit local wineries and breweries and sample the town’s finest beverages.

Day 7: Take a day trip to nearby attractions like Annapolis or St. Michaels.

Food and Drink Scene of Chestertown

Chestertown is home to a diverse range of restaurants, cafes, and bars that offer something for every taste and budget. Here are some must-try dishes and local beverages:

Must-Try Dishes

  • Crab Cakes: This Maryland classic is a must-try dish in Chestertown. Head to the Fish Whistle at the Granary for some of the best crab cakes in town.
  • Oysters: Chesapeake Bay oysters are a local delicacy and can be found on the menus of many of Chestertown’s seafood restaurants.
  • Fried Chicken: Nothing beats homemade fried chicken. Visit Luisa’s Cucina Italiana for some of the best fried chicken in town.

Local Beverages

  • Craft Beer: Chestertown is home to a thriving craft beer scene, with local breweries like Eastern Shore Brewing and Bull & Goat Brewery.
  • Wine: Kent County is home to several acclaimed wineries, including Crow Vineyard and Broken Spoke Vineyard.
  • Black Eyed Susan: This refreshing cocktail can be found at many local bars and is made with rum, vodka, orange juice, and pineapple juice.

Where to Stay in Chestertown: Hotels, Hostels, and Guesthouses

Chestertown offers a variety of accommodation options, from quaint bed and breakfasts to luxurious hotels. Here are some options:

  • Brampton Bed and Breakfast Inn: This historic inn is located in the heart of Chestertown and offers cozy rooms, gourmet breakfasts, and beautiful gardens.
  • The Imperial Hotel: This elegant hotel is housed in a beautifully restored 19th-century building and offers spacious rooms and suites with modern amenities.
  • Quality Suites: This budget-friendly hotel is located just outside of Chestertown and offers spacious suites with kitchenettes and free breakfast.

What to Buy in Chestertown: Souvenirs and Local Products to Bring Home

Take home a piece of Chestertown with these must-buy souvenirs and local products:

  • Crab-themed souvenirs: Whether it’s a mug, a keychain, or a t-shirt, be sure to pick up some crab-themed souvenirs to remember your trip to Maryland.
  • Local wine and beer: Stock up on the town’s finest wines and craft beers to bring back home with you.
  • Artisanal products: Chestertown is home to many talented craftsmen and artisans. Visit the town’s specialty shops and galleries to find unique and handmade products.

Local Culture and Customs of Chestertown

Chestertown has a rich cultural heritage and is proud of its colonial history. Visitors to the town should respect the local culture and customs and be mindful of the historical significance of the town’s landmarks and attractions.

Best Time to Visit Chestertown

The best time to visit Chestertown is during the spring and fall when the weather is mild and the town hosts many outdoor festivals and events.

Do’s and Don’ts of Chestertown

Do:

  • Respect the town’s history and culture.
  • Visit the local museums and historical landmarks.
  • Try the local seafood.

Don’t:

  • Litter or damage any of the town’s natural attractions.
  • Disrespect the town’s historic buildings or landmarks.
  • Overlook the town’s thriving arts scene.

Safety and Health

Safety in Chestertown

Chestertown is a safe town with a low crime rate. Visitors should be aware of their surroundings and take normal safety precautions.

Health in Chestertown

Chestertown has excellent healthcare facilities and visitors should have no trouble finding quality medical care if needed.

Getting to Chestertown: Transportation Options and Logistics

Airports Near Chestertown

  • Baltimore/Washington International Thurgood Marshall Airport (BWI): Located 68 miles from Chestertown.
  • Philadelphia International Airport (PHL): Located 94 miles from Chestertown.

Bus Stations Near Chestertown

  • Greyhound Bus Station in Aberdeen: Located 27 miles from Chestertown.

Other Options

  • Car Rental: Visitors can rent cars from several car rental companies located at nearby airports or in Chestertown.
  • Amtrak Train Station: The closest Amtrak train station is in Aberdeen, located 27 miles from Chestertown.

How to Get Around in Chestertown

Chestertown is a small town that can easily be explored on foot or by bike. Taxis and car rentals are also available.

Where to Go Next from Chestertown: Nearby Destinations and Excursions

  • Annapolis: Visit the state capital of Maryland and explore its charming historic district and beautiful waterfront.
  • St. Michaels: Explore this quaint town’s shops, restaurants, and museums and enjoy scenic views of the Chesapeake Bay.
  • Washington, D.C.: Take a day trip to the nation’s capital and visit its iconic landmarks like the White House and the Smithsonian museums.

Conclusion

Chestertown is a hidden gem in the Eastern Shore that offers a unique blend of history, culture, and scenic beauty. Whether you’re interested in exploring the town’s museums and historical landmarks, or simply want to relax and enjoy the natural beauty of the Chesapeake Bay, Chestertown has something to offer for every type of traveler. Come visit this charming town and discover all that it has to offer!

The Chester River The Chester River High Street in the Historic District High Street in the Historic District