Kent Island Guide: Enjoy a Day Trip from Annapolis, Maryland

Visiting Annapolis, Maryland? Then consider spending the day on nearby Kent Island. As the largest island in the Chesapeake Bay area, this destination offers history, fun things to do and raved-about dining. Why wait to plan a day trip? Check out this Kent Island guide and plan a quick trip.

Kent Island Guide: Where to Go and Things to Do

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Photo: Joe Haupt

Where is Kent Island?

Kent Island is located at the base of Chesapeake Bay Bridge. The island connects Maryland’s east and west shores, and offers a quaint destination. To get here, just head west of Maryland and drive over the bridge. Cities on Kent Island include Centreville, Grasonvile and Stevensville.

The Island’s History

Kent Island was the first European settlement in what is now Maryland. Before settlers arrived, the island served as home to the Matapeake tribe, members of the Algonquin nation. Over the years, the area provided trade transportation routes, and played a part in various industries. Today, visitors enjoy historical sites, natural attractions, local shopping and plenty of flavor.

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Kent Island Guide to Activities

Natural attractions and outdoor activities are a big draw. Kent Island welcomes people from Annapolis, Baltimore and Washington D.C., who are searching for a quiet place to relax and make memories.

Start at Matapeake Beach. This spot provides a place for water lovers to swim, enjoy picnics and let their dogs play. For more water recreation, visit Matapeake Pier and Boat Ramp and Romancoke Pier and Kayak Ramp. Both places offer opportunities to rent boats, paddle and fish. The area also houses more than a dozen marinas, such as Kent Point, Kentmorr and Safe Harbor Narrows Point.

After spending time on the water, plan adventures on land. Popular attractions include Chesapeake Exploration Center, Bloody Point Bar Lighthouse and Chesapeake Bay Environmental Center. Visitors also enjoy biking and hiking trails, nature photography, and wildlife-watching.

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Where to Eat

Kent Island has a longtime reputation for fresh seafood. Plus, there are places for pizza, burgers, sushi, comfort food and special tastings.

When it’s time for a break, enjoy both waterfront dining and indoor spots. For seafood, try Fishermans Inn, The Narrows Restaurant, Kentmoor Restaurant and Crab House, and Boatyard Bar and Grill.

Those looking for something different should visit Frix Fire Grill, Cafe Sado and Carmine’s NY Pizza Kitchen. Kent Island also has popular chains like Cracker Barrel, Subway and Chick Fil-A.

Shopping Kent Island

While exploring Kent Island, don’t forget to support local businesses. There are plenty of quaint shops scattered throughout the island, as well as a farmers market, distilleries and winery.

Historic Stevensville Arts and Entertainment District has more than 24 art galleries, boutiques and historical sites. Shoppers will find antiques, souvenirs, handmade creations, fashion, jewelry and more items only found on Kent Island. Other small districts include Rainbow Plaza, Thompson Creek Shopping Center, Kent Towne Market and Kent Landing.

After exploring Kent Island, find some things to do in Annapolis. Then book an Annapolis vacation rental home and escape today.