What to do on Kent Island

Kent Island is right across the Bay Bridge in Maryland. It’s an often overlooked destination as it’s on the way to beach destinations like the Eastern Shore, Ocean City, and Rehoboth. The island is the largest in Maryland and surrounded by the Chesapeake Bay. If you’re wondering what to do on Kent Island, my mini guide will give you all the info you need for a day trip or a break when driving to/from the beach.

Kent Island History

Kent Island has a history of nearly 12,000 years of habitation. The Matapeake tribe, part of the Algonquin nation, were the more recent native inhabitants and called the island “Monoponson.” They lived peaceful lives, focused on hunting, gathering, fishing, and planting. In 1631, William Claiborne established the first permanent European settlement in what is now Maryland on Kent Island, creating a trading post and agricultural community. In the 19th and 20th centuries, the development of ferry routes and bridges shifted the island’s economy from agriculture and trade to seafood harvesting and tourism, which continue to thrive today. Read more about the history here.

Be sure to check out the Kent Island Heritage Society which has sites open on the first Saturday of April to November from 1-4 pm.  There is also a historic Stevensville walking tour map from the heritage society available here.

The Chesapeake Heritage & Visitors Center is open Monday-Friday (ironically not on the weekends when you’d actually expect tourists…). I peaked my head inside the building and it didn’t look too exciting.

Where to Eat and Drink on Kent Island

The best lunch and coffee combo is Harris Crab House and Dessert First. The only downside of these two excellent restaurants being right next to each other is having a large enough appetite to handle both!

Harris Crab House is a classic Maryland seafood experience. You can get fresh seafood and crabs by the dozen, po-boys, fish sandwiches, and everything in between.

My mom got a crab cake (which came with two sides and a piece of delicious corn bread). And I got a soup and half-sandwich combo (available during weekdays only) with the Maryland seafood soup and a catfish sandwich. We spent $50 for our lunch.

Then, we walked into Dessert First for coffee and cake. Unfortunately, we were wayyyy too stuffed from our lunch to be able to indulge. Instead, we’ve planned to return again soon and only get coffee and cake. Just look at these cute drink specials!

Visit Cascia Winery on the weekends between 12-4pm and check out their events.

If you’re into beer, check out Cult Classic Brewing.

Where to Shop Around

The best shop I came across on Kent Island is Ophiuroidea. My mom and I wandered the shop for almost an hour, going round and round. There are several unique gifts (for yourself or others…) with beach themes. You can also find food, beauty, home goods, and jewelry items made by local artists from Maryland and other beachy destinations on the East Coast.

Although Anchors & Oars was closed when I was figuring out what to do on Kent Island, it has sailing and boat themed home décor.

Visit art galleries Kent Island Federation of Art (which is only open between 1-4pm Friday through Sunday) and My Little Studio (generally open everyday between 11am-4pm, check for the day you want to visit).

Hiking and Biking

If you’re visiting the Chesapeake Heritage & Visitors Center, leave your car parked and do the short but lovely walk up to Ferry Point Park. My mom and I saw several Red-winged blackbirds while walking around. There is also a small beach where you can go swimming.

Also, check out the Cross Island Trail in Terrapin Nature Park or the South Island Trail for hiking and biking.  

Practical Tips

• The best day to visit Kent Island is a Saturday. All of the shops will be open as will the heritage society.
• The Bay Bridge is a toll road and varies in cost if you are an EZ pass customer or not. Check the rates here.
• You need a car to explore Kent Island. Most of the destinations I’ve mentioned are not connected with sidewalks, unfortunately, and can be far apart. Biking could be an option but be weary of cars fed up with Bay Bridge traffic. There are no consistent bike lanes.
• You’ll just need a half-day to explore around.