Visit the Scenic and Historic Kent Island, MD

When cruising the Chesapeake Bay and reaching the midsection where the Bay Bridge straddles the Eastern and Western shores, many boaters think of Kent Island as just a convenient stop for fuel and provisions. But taking time to explore this island reveals a lovely destination teeming with an array of amenities and attractions.

As the largest island in the Bay (nearly 32 square miles), its 157 miles of shoreline offer plenty of places to dock. Most of the restaurants, bars, hotels and commercial activity happens along Route 50, especially around Kent Narrows, the passage spanned by a bridge that delivers guests to Maryland’s Eastern Shore. The lower part of the island is home to gracious homes, cornfields and coves where watermen harvest their daily catch.

Terrapin Nature Park, on the northwest section of the island, is home to a 3.2-mile walking trail that presents spectacular views of the Bay Bridge and introduces hikers to woodlands, tidal pools and wildlife. Walkers and bikers relish the flat, easy terrain. A few miles south, Matapeake Park offers a clubhouse, picnic area, woods for shade and a beach with a canine section where the entire crew — including Fido — can take a dip.

Along Route 50, the busy highway that leads to the Delaware beaches, stands an historic marker that declares this land in 1631 became the first English settlement in Maryland and the third oldest in America after Jamestown, VA, and Plymouth, MA. For centuries, the island was home to fishing villages and farms. The walking tour of Stevensville showcases the Victorian architecture in restored houses and train station.

Modern attractions include some unexpected amenities: two small airports located near marinas and two vineyards (Love Point Vineyards and Cascia Vineyards) on gorgeous waterfront properties. Cult Classic Brewery and Oh My Chocolates round out the secret indulgences.

Take a tour of Paul Reed Smith Guitars that designs instruments for celebrity musicians such as Carlos Santana and John Mayer, putt on smooth greens at Blue Heron Golf Course, or enjoy a seagull’s perspective on Delmarva Balloon Rides.

When all this outdoor fun leaves you wanting a bite or a brew, Kent Island’s restaurants accommodate any whim from the casual Big Owl’s Tiki Bar to the upscale Kent Island Resort. Most are clustered around Kent Narrows; all present stellar sunsets.

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WHERE TO DOCK

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Bay Bridge Marina
410-643-3162
Conveniently located at the base of the Bay Bridge, this marina accommodates vessels from 30 to 50 feet. Resort-level amenities include fuel, full-service yacht yard, two ship stores, bar and restaurant, swimming pool and more.

Kentmorr Marina
410-643-0029
This angler’s paradise hosts 20 charter boat captains for excursions to hook rockfish, bluefish and other delicacies. Vessels up to 45 feet are welcome, and guests enjoy amenities such as fuel, two fish-cleaning stations, and a restaurant and tiki bar with a view of the bridge.

Piney Narrows Yacht Haven
410-643-6600
The sheltered marina offers 278 open and covered slips for boats up to 67 feet. Pump out is free with fuel purchase, and repair services are on-site. Other amenities: swimming pool, picnic area, boaters’ lounge, nearby restaurants, bars, charter captains and great destinations nearby.

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WHERE TO DINE

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Amalfi Coast
443-249-3426
Classic coastal Italian cuisine, from fresh insalate to pasta and pizza, gets rave reviews at this cozy eatery in historic downtown Stevensville.

Libbey’s Coastal Kitchen & Cocktails
410-604-0999
Under new management this year, Libbey’s presents spectacular sunsets over the Bay Bridge at its indoor seating and large outdoor deck, while serving a nice sampling of dishes from the land and sea.

Kentmorr Restaurant & Crab House & Dirty Dave’s Tiki Bar
410-643-2263
Since 1954, this crab house has impeccably prepared Chesapeake cuisine at a charming marina. The thatched roof tiki bar on the beach creates a kick-back summer vibe.

Harris Crab House
410-827-9500
Family-owned for five generations, this iconic Bay eatery serves regional seafood year-round, featuring local steamed crabs, oysters and fried rockfish. The seafood processing plant next door guarantees freshness with every bite.

Red Eye’s Dock Bar
410-304-2072
This recently expanded hot spot delivers entertainment from the lone acoustic guitarist to six-piece rock bands and the Father’s Day Bikini Contest. Pub food covers the standards with wings, sandwiches, nachos, crab cakes and more.

Fisherman’s Inn & Crab Deck
410-827-6666
For decades, this traditional crab deck and seafood house has welcomed visitors to Maryland’s Eastern Shore cooking with a fantastic waterfront view and steamed crabs and oysters from the region.

Bridges
410-827-0282
Bridges’ open and breezy design sets a beautiful stage for dining indoors or on its expansive deck. The chef takes a contemporary spin on fresh seafood, sandwiches, salads and pizza, while guests relish spectacular Kent Narrows views.