Chestertown MD: Top 10 Things That You Need to See and Do Here

What comes to your mind about the Eastern Shore of Maryland? We think of the area's breathtaking views, rich history, and thriving arts scenes. The charming city of Chestertown is a small hamlet within the heart of the Eastern Shore of Maryland. It is a beautiful and must-visit destination in the region.

What are the top 10 things to do in Chestertown?

Chestertown is a gem and is the largest town in Kent County. Here, you can spend your days touring Washington College, relaxing in nature, and enjoying its delicious seafood cuisine. With this in mind, our Chestertown realtors have put together 10 things you can do during summer in Chestertown and its surrounding areas. Let's take a deep dive, shall we?

1. Experience Its Unique Culture and Historical Background

Travels expose you and open your mind to new and different aspects of life. You tend to learn a lot when you visit a new destination. If you want to experience a new and vibrant culture, the Eastern Shore of Maryland is your perfect destination. During Memorial Day weekend at the Chestertown Tea Party Festival, people from far and near gather to reminisce about the colonial history that dates back to the 17th century. The Chestertown Historic District boasts an array of historic sites and museums that inspire visitors to come here and experience Kent County's unique culture and history. Don't forget the Kent County Fair held annually on the third weekend of July. There are tons of activities and entertainment for all ages!

2. Enjoy Some Delicious Seafood

Maryland is well-known for its delicious coastal cuisine. Here, there is no shortage of delightful and delicious restaurants to get a taste of the region. If you haven't tried it yet, there is no better time than the summer! Oysters, blue crabs, rockfish, you get the idea… endless options! Here are the top suggestions of pleasant restaurants you can find in or around Chestertown:

• Watermen's
• 98 Cannon Riverfront Grille
• Barbara's on the Bay
• Harbor Shack
• The Fish Whistle

Maryland Blue Crab straight out of the Chester River, Chestertown, MD

3. Celebrate the Season

The Eastern Shore of Maryland offers a variety of festive events during the summer. Experience Chestertown like a local and enjoy one of the many unique annual events (the Independence Day Extravaganza Cruise and "Music in the Park" Summer Concert Series). You could also check out the Dogwood Festival in Galena in May or the Pirates and Wenches Fantasy Weekend in Rock Hall in August.

4. Reset in Nature

Summer is the best period to discover/rediscover who you are. It is the best time to reset in nature! Staying outdoors can ignite your senses, spark your creativity, and enhance your memory. Spend a day or two by the Chester River, and enjoy the fresh air while unplugging and recharging your energy. Eastern Neck Wildlife Refuge and Turner's Creek are great areas for day trips and have plenty of trails to walk.

5. Walk, Run, and Bike along the Chestertown Rail Trail

The Chestertown Rail Trail is a beautifully peaceful, paved path that connects Washington College to the business district of Chestertown. This area is perfect for foot traffic and cycling. If you time your trip just right, there are numerous 5K races to participate in that will allow you to enjoy the beautiful scenery Kent County has to offer.

6. Go on a Shopping Spree

There's no better place to be if you are seeking to have a good shopping experience. Chestertown is brimming with fantastic shops such as Mimi's Closet, Twigs and Teacups, and Chester River Wine and Cheese Company where you can get countless unique goods or items. If you plan a weekend here be sure to stop by Fountain Park and check out the Farmer's Market! You will be glad you did. While you are at it, stop into the Coldwell Banker Chesapeake Real Estate office and find Billy Sutton and Lacey Sutton to discuss a longer-term stay!

7. Go Fishing!

You can go out on the Chester River or the famed Chesapeake Bay on a charter boat. Most offer full or half-day charters and can put you on large rockfish. Most folks get a group of friends or family together and enjoy a relaxing day on the water. Remember the seafood cuisine from earlier? Why not catch your own?

8. Catch a Movie

Relax and take in a movie at Chesapeake Movies. This is great for a rainy day and you will have 5 screens to choose from. This renovated and state-of-the-art theater offers reclining seats, appetizers, and digital projection screens!

9. Explore the Art on High Street

There is no better way to know a place than by exploring its local art scene. Creators and lovers of art will feel very much at home here! The Chestertown area has many high-quality theaters, galleries, and unique architectural structures. Here, you'll find ways to enjoy the works of Maryland's best creatives. High Street in Chestertown offers several all within a short walk of one another.

10. Have Fun in the Sun at the Beach

We cannot finish this wonderful piece of writing without mentioning having a fun moment at the beach. Your summer vacation will not be complete if you do not visit Chestertown's nearby beaches. Yes, you read that right! Some of these include Betterton Beach, Conquest Beach, and Ferry Park. There is nothing better than lounging in the sun by the water with the sand and water touching your legs. This is one of the best things to do in Kent County, MD during the summer. So, do not miss the opportunity to experience and enjoy the best beaches in Kent County.

Whether you are vacationing on the Eastern Shore of Maryland to go on a shopping spree, enjoy the delicious coastal cuisine, have fun at the beach, or rest in nature, you are guaranteed to make memories here that will last a lifetime.

Want to buy a home in Chestertown?

Are you thinking of making a move to the Chestertown, MD area, Kent County, or anywhere on the Eastern Shore? Contact Billy Sutton, Realtor at Coldwell Banker Chesapeake Real Estate, or Lacey Sutton, Realtor at Coldwell Banker Chesapeake Real Estate. We are local and experienced real estate agents serving the Upper Eastern Shore who are based out of Chestertown. Call 443-480-2447 to get in touch with us for real estate services in Chestertown and its surroundings.