Kent Island

Understand

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 settlement 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

By car

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 $4 eastbound only, as of July 2019). After crossing the bridge, you're there! Exits 37 and 41 provide access to the island's major tourist attractions.

By plane

• Bay Bridge Airport (FAA:w29) is a small, regional airport with no scheduled commercial flights. Private planes park within walking distance of Hemmingway's restaurant and Kent Island Depot (a deli). Taxis, rental cars, aircraft rental, flight training, and aircraft maintenance are available
• Kentmorr Airpark (FAA:3W3) is a small grass airstrip with no scheduled commercial flights. Private planes park within walking distance of the Kentmorr Restaurant & Crabhouse and the Kentmorr Marina. Cab transportation to town is also available.

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 unfortunately 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. With the new trails, future trips to Kent Island may involve getting around by bike instead of by car, just be ready for the workout; Kent Island already has over 12 miles of trail!

Go next

Annapolis and Cape St. Claire are on the other side of the Bay Bridge, and Grasonville, Centreville, and Wye Mills are on the other side of the Kent Narrows Bridge. Grasonville is immediately past the bridge and beyond it lies Queenstown, the location of the Queenstown Prime Outlets which offer designer outlet shopping. Beyond Queenstown you have a choice of going north along Route 301 to Centreville and the upper counties, and southeast along Route 50 to Wye Mills and the lower shore. You can also go to Baltimore or Washington, D.C., home to historical places, national monuments, museums, aquariums, and the U.S. Capitol Building and the White House.