explore the island

We have loved exploring all that Kent Island and the surrounding areas have to offer, and we’ve only scratched the surface. Here are some of our favorites and recommendations for fun times on the bay!

Waterfront/Outdoor Restaurants:

  • Fisherman’s Inn Crab Deck: amazing crab dip & crushes. Indoor dining is good too next door!
  • The Jetty: fun bar atmosphere. Some indoor seating. Sometimes has live music on weekends
  • The Big Owl Tiki Bar: right on the water, bar food – great scenery
  • Harris Crab House: can be great for outdoor dining! Stop by Rise Up & Desserts spot next door after!
  • The Narrows & Bridges: both pricier, but great for a date night, delicious food, and great view!
  • Kentmorr Restaurant/Dirty Dave’s Beach Bar: Restaurant is not bay view (is marina view!), but during the summer you can make reservations on the weekends for the beach area and do take out from the restaurant to enjoy the beach (no reservations required during the week). There is a 21+ bar area on the beach that does not require reservations. 

Not Waterfront – Still Good:


Adult Beverages:

Outdoor Activities:

  • “Nemo” trail: accessible by bike or car from our house, equestrian trail that has amazing fields of flowers in the summer. Keep an eye out for poison ivy along the edges of the path. Still gorgeous in the fall/winter too! A few loops that go around lets you pick your length. 
  • South Island Trail: head out right from our house and meet up with the trail. Go either way to explore the island – keep in mind it is a very sunny trail at parts
  • Cross Island Trail: amazing trail for biking. Park at Terrapin State Park for the beginning of the trail. Want to skip ahead? Parking is allowed at Shore United Bank 300 Castle Marina Rd along the trail side. Stop by the Chesapeake Heritage & Visitor Center!
  • Matapeake Beach (& dog beach): a larger beach with great views of the Bay Bridge. Parking lot fills up quick on nice weekend days. Less than .5 mile walk to the beach. Portable bathrooms on site.
  • Chesapeake Bay Environmental Center: A handful of trails with some cool views of the marsh, beach, and small information center. Another great place to rent a kayak!
  • Terrapin Nature Park: can get very crowded on the summer weekends. Great views of the bay and access to beach.
  • Blue Heron Golf Course: quick, easy, executive course (really close)
  • Queenstown Harbor Golf Course: stunning course, a bit pricey


Day Trips: