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Kent Island

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Kent Island

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Kent Island is located in the Chesapeake Bay at the eastern end of the Chesapeake Bay Bridge and is quickly becomming a popular tourist destination in Maryland. Kent Island is a great place to sample authentic Maryland seafood, take a historic stroll, or enjoy a trip out on the Chesapeake.


Kent Island has a rich history dating back to 1631, when William Claiborne of Jamestown first set up a trading post on the island. It is said that Claiborne liked being on Kent Island so much that he decided to make it his permanent home, and he started what would become the oldest English settlment in Maryland. Ever since then Kent Island has thrived as the crossroads of the Chesapeake. Several people, from founding fathers en route between Annapolis and Philadelphia, to vacationers on their way to Ocean City, have visited the island. Many of them, like Claiborne, have even liked Kent Island so much that they decided to move there.

Get in

From Washington, take U.S. 50 east towards Annapolis, or if you're coming from the Baltimore area, take I-97 south to U.S. 50 east. Then, from Annapolis, follow U.S. 50 east towards the Bay Bridge (toll for the bridge is $2.50 eastbound only). After crossing the bridge, you're there! Exits 37 and 41 provide access to the island's major tourist attractions.

Get around

The main way to get around Kent Island is by car, at least for now. Routes 8, 18, and 50 are the main roads to take from place to place, but if you want to go on foot or on bike, you can use the hiker-biker trails. The Cross Island Trail, as its name implies, goes across the island from Terrapin Park to Kent Narrows, and the Kent Island South Trail goes from Matapeake Park to Romancoke Pier. The trails unfortunatly do not connect with each other, but there are plans to fix that in the future along with another trail south of Route 50, connecting Kent Narrows with Chester.


  • Historic Stevensville, located along the southern part of Love Point Road and East Main Street in Stevensville. Kent Island's historic downtown area has restored historic buildings, preserving its 19th Century small-town feel to this day. The area also offers shopping and dining. To get there, take Exit 37 to Route 8 north, then follow the signs to Stevensville and Historic Stevensville.


  • Chesapeake Bay Bridge Walk, Chesapeake Bay Bridge, [1]. The Bay Bridge Walk offers a unique opportunity to take a 4.3-mile walk across the Chesapake Bay Bridge, which is currently the longest bridge in Maryland. The walk is usually held the first Sunday of May, but it's not held every year, so you'll have to check the website ( for details about any upcomming walk.



  • Annie's Paramount Steak House, 500 Kent Narrows Way N, Grasonville, tel. 410 827-7103, [2]. Also serves seafood.
  • Kent Manor Inn and Restaurant, 500 Kent Manor Drive, Stevensville, tel. 410 643-7716 (for dining), [3].
  • Kentmorr Restaurant and Crab House, 910 Kentmorr Road, Stevensville, tel. 410 643-2263, [4]. Offers inside and outside dining and also features both inside and outside bars. There is a nice sandy beach behind the restaurant, open to public.



  • Comfort Inn, 3101 Main Street, Grasonville, tel. 410 827-6767.
  • Kent Manor Inn, 500 Kent Manor Drive, Stevensville, tel. 410 643-5757 (for lodging), [5]. An expensive, but beautiful, country inn located just off of Route 8 near the Bay Bridge Airport, and across Route 50 from Historic Stevensville.

Get out

Annapolis is right on the other side of the Bay Bridge, and St. Michaels is just south of Kent Island for those travelling by boat. For the shoppers, the Queenstown Prime Outlets are just minutes to the east at the 50/301 split.

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