Just across the Chesapeake Bay Bridge, into Maryland’s Eastern Shore, sits an often overlooked destination – Kent Island. Kent Island, as I discovered on a recent trip there, is a relaxing getaway brimming with several nature areas and walking paths, waterfront restaurants serving up fresh local seafood, and a laid back culture that can only be found by the water. Here’s how my family and I spent our day on the island.

Paddle Boarding

My first to-do once arriving on the island was to get a workout in with the fine folks of Dragonfly Paddle and Fitness. I’ve written an entire post on my experience paddle boarding with them, but I can assure you that paddling through the marshes and inlets along the coast of the island was a serene experience I look forward to trying again.

Terrapin Beach Park

Next up was Terrapin Beach Park, a waterfront park on the island. The Cross Island trail runs through the park and across the island, leading way to forested, waterfront, and marshy scenery.

Terrapin Beach Park is also right next to the Chesapeake Bay Bridge, which is a beautiful bridge and at four miles long, connects Maryland’s Western and Eastern shores. If you go to the area of Terrapin Beach Park that is closest to the bridge, you can marvel at the bridge from a unique vantage point.

Cascia Vineyard & Winery

Cascia Vineyard & Winery is Kent Island’s only winery, and was a delight to visit. Mark Cascia, the owner himself, did a portion of our wine tasting, which was just the right mix of whites and reds and reasonably priced at $10. As they were bottling the day we visited, Mark had me try out a new 2015 red blend that wasn’t even on the tasting menu yet –  I was more than happy to oblige to be his taste tester!

With a glass of wine later purchased and in hand, we made our way out onto the winery’s patio and lawn overlooking Cox Creek. Unlike the overcast morning, the sun had decided to come out and provide a pleasurable place to sip and gaze at the view.

Kentmorr Restaurant and Crab House

The restaurant that I had heard high praises of from Kent Island locals was the Kentmorr restaurant. At Kentmorr the menu was plentiful with seafood options, the cuisine that Maryland is most known for. I ordered the soft shell crab dinner, which was fresh and savory. Being by the water also makes me crave Key Lime Pie, so we shared a slice of its tangy goodness as well.

In addition to the main restaurant, Kentmorr has an entire fun-filled outdoor bar called Dirty Dave’s Tiki Bar right on the water. We made our way over to Dirty Dave’s to enjoy a drink while listening to a live band. There’s a beach that both kids and adults alike were enjoying, as well as games, hammocks, and comfortable Adirondack chairs.

To make a weekend of it, head to Annapolis…

If you want to make a weekend out of your visit as we did, Annapolis is a short twenty minute drive away. In Annapolis we walked around the historic downtown, and took a boat ride out on the Severn River.

Have you been to Kent Island? Would you want to go?