The Best Places to Hit During Family Weekend

Having spent more of the past few years in Chestertown than my hometown, I’ve had enough time to figure out the places to take friends and family when they’re only here for a short visit. Although this list is brief, it is not exclusive of all of the wonderful spaces and places in this town not mentioned, nor does it mean they are any less worthy. I highly encourage all freshman to spend the next four years getting to know your new home away from home inside and out, as that’s one of the best ways to be a happy human here in the Washington College community. Here is a list to get you, and your family, introduced to Chestertown for this upcoming Parent’s Weekend!


The Fish Whistle – 98 Cannon St, Chestertown, MD

At the end of Cannon Street, The Fish Whistle sits overlooking the water of The Chester River. When you’re in need for seafood, this is the place you want to be. From clams and mussels to shrimp and many types of fish, The Whistle covers all of the bases. My personal favorite is Lisa’s Crab Dip and Pretzel Bread. There is nothing better than creamy crab dip on top of fluffy, toasted pretzel rolls. However, if you’re not so much of a seafood fan The Fish Whistle still has options for you! Take your pick from salads, sandwiches, and some home-style comfort food. And if those still aren’t your taste, The Fish Whistle’s sunset views are enough for anyone.

Downtown Shops – High St & South Cross St., Chestertown, MD

After grabbing a bite at The Whistle, make your way up from the water to High Street to see the array of shops. There’s sure to be something for every member of the family. Stop into Music Life to take in all of the beautiful instruments surrounding the walls, or step into She She on High to admire some bohemian homeware! A bit of a wander from High, onto South Cross Street, are a few other shops that have many eye-catching items. Twigs and Teacups is your go-to stop for any souvenir-y, coffee table display trinkets, and you won’t be disappointed. Across the street from Twigs and Teacups is Bookplate, a bookstore full of new and old, worn and untouched books in any and every genre.

Figg’s Ordinary – 207 South Cross St #102, Chestertown, MD

If you’re in the mood for a refreshing salad or sandwich, stop into Figg’s Ordinary for a healthy pick-me-up, especially those with specific dietary lifestyles such as veganism, vegetarianism, and gluten free. Figg’s is a calming and satisfying environment to chat with some friends, read a book, get some work done, or eat some yummy treats. Their dishes range from breakfast and lunch, to bakery desserts and coffee. Figg’s Ordinary is also an environmentally friendly restaurant, working towards their goal of being a zero-waste business. Whether you want to sit down and have a moment to yourself or just stop in for a delicious vegan chocolate chip cookie and a coffee, Figg’s is a pleasant place to visit.

The Freeze – 717 Washington Ave., Chestertown, MD

Another spot for sweet treats is outside of the downtown center and past the college. The Freeze is one of WC students’ favorite places to celebrate the end of an exam week, satisfy your sweet tooth, or to remind yourself of your favorite childhood foods. Offering ice cream cones, milkshakes, burgers, sandwiches, and fried foods, it’s a great place to grab dessert, or a snack, with your family before heading down to the water to watch the sunset.


Wilmer Park – 413 South Cross St., Chestertown, MD

After getting ahold of your frozen treats from the Freeze, Wilmer Park is a great place for you to watch the sun settle into the horizon. You have your pick from sitting and laying in the large grassy area just before the water or relaxing on the benches that look over the river in the recently built gazebo that sits high and tall. If you want a water view, this is where you’ll find it. Pack your family a picnic or just take a stroll: Wilmer Park is the best place to soak in the town’s beautiful surrounding nature.

Crow Vineyard – 12441 Vasant Corner Rd., Kennedyville, MD

One of the best things about Chestertown is its compact size – and the fact that you can get from one side of town to the other within a five-minute drive—but sometimes the only thing you need is to take a break from it. In times like those, Crow Vineyard is the perfect place to get a nice breath of fresh air twenty minutes away from campus. The Vineyard hosts many different events and activities open to the public, a favorite being their Farm to Table Brunch on Sundays. For $27 dollars per person, one can enjoy a locally grown, savory, buffet style breakfast that they’re bound to remember.

These are just a few of the many wonderful restaurants and shops that fill the streets of Chestertown. Try some of these places out or feel free to investigate onward from these suggestions. Whatever you find, you’re sure to enjoy.


Samantha Clark

Staff Blogger

Photos by Jenna Sutcliffe

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