Kent Island, MD

Mark’s Score   8.2

To most people Kent Island is just an extension of Annapolis that must be endured on the way to beach. It is true, that from Rte 50, all you see are strip malls. However, behind the malls Kent Island is chock-a-block with scenic trails, historic villages, vineyards, marinas, beaches, cozy little inlets, and sweeping marshlands. All you need do is get off the highway.

Kent Island is a low-lying island stretching 18 miles (29 kilometers) from the eastern shore deep into the Chesapeake Bay, shrinking the bay to its narrowest width. There are no incorporated towns on the island, but there are several unincorporated villages; Stevensville, Chester, Grasonville, Romancoke, and Love Point. The island is separated from the Eastern Shore by the Kent Narrows.

The first permanent English settlement in Maryland was established on Kent Island by William Claiborne (from the Virginia Colony), who set up a trading post in 1631. However, King Charles I granted Maryland (including Kent Island) to George Calvert 1st Baron Baltimore. The conflicting claims of Lord Baltimore and Claiborne lead to the first armed conflict between the English colonies lasting through most of the 1630s.  

The Calverts eventually won that conflict and Kent Island thrived in the 1600s as a plantation-based economy growing tobacco and grains. By the 1700s Kent Island became a center of fishing, oystering, and shipbuilding. It remained largely rural with an agriculturally based economy until the Bay Bridge was built in 1952. After the construction of the bridge the Island became a suburb of Annapolis and the focus of the island’s economy sifted from agriculture to leisure and retail.

One of the reasons I moved to Delmarva was because it has a number of quaint historical villages. Though Kent Island is the longest settled part of the state, much of its historical architecture has long since been overrun by urban sprawl. But it is not all gone. Stevensville is a charming little village with many historical buildings in its historic district. Of particular note is Christ Church, built in the Queen Anne style with its lancet chimney. 

If you are into wine, there are three vineyards on Kent Island, growing a number of varieties from Gruner Veltliner to Sangiovese. There is also a craft brewer. You could spend an entire day tasting Kent Island wines and beers. If you get hungry along the way, there are a number of good to excellent restaurants, many of which have water views.  

The island is not conducive to walking, that suburban sprawl again. The streets are narrow and there are few sidewalks, but the island is cut by multiple inlets which afford bay views from your car.  However, there are many parks offering bay and marsh views, and plenty of opportunities to hike and kayak and commune with nature. Terrapin Park offers great views of the bridge. While the Chesapeake Bay Environmental Center offers many recreational activities while preserving bay habitats. 

Which Delmarva cities and towns should you visit?

Places Rated in or near Kent Island.

2025 Feb

Amalfi Coast

Restaurant/Italian

9.47

2025 Feb

My Little Studio

Retail/Art Gallery

9.40

2025 Sep

The Narrows

Restaurant/Seafood

9.10

2026 Aug

Chesapeake Bay Environmental Center

Park

9.07

2026 Aug

Bridges

Restaurant/Seafood

8.68

2026 Mar

Bark Barbecue

Restaurant/Barbecue

8.60

2026 Mar

Terrapin Nature Park

Park

8.42

Places reviewed in or near Kent Island

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