The Chesapeake Bay Environmental Center offers guided kayak tours. Photo by Courtney Leigh.

It’s impossible to cross the Chesapeake Bay Bridge and head to Easton or Rehoboth Beach without driving through Kent Island, and yet few travelers even realize they’re on an island when they reach the eastern side of the 4.3-mile overpass. At this point, bridge-lovers are still exhilarated from the view; beach-going parents are busily catering to the needs of the tiny tourists in the back seat; and those who fear the bridge are trying to rediscover their resting heart rate.

But this small patch of land in Queen Anne’s County, Maryland, is more than just a pass-through on the way to vacation destinations. Surrounded by the Chesapeake Bay and a few smaller bays, cleaved by twisty creeks and rich with wildlife and natural habitats, the island, which offers 157 miles of shoreline, has a charm of its own.

Views of the Chesapeake Bay abound on Kent Island, a patch of land just east of the Bay Bridge. Photo courtesy of Queen Anne’s County Tourism.

Originally the home of the Native American Matapeake tribe, who referred to the island as Monoponson, the island in its present form is made up of two incorporated towns—Stevensville and Chester.

The tribe held onto it for more than 10,000 years, according to the Kent Island Heritage Society, until William Claiborne landed there in 1631, changed its name and made it “the first permanent European settlement in what is now Maryland.”
The thing about Kent Island is that it doesn’t look all that special when you’re whizzing by on the merged Routes 50/301. Aside from the water, which is viewable from just about everywhere, its other virtues require a little digging.

Cyclists can pick up the Cross Island Trail or the South Island Trail at Terrapin Natural Park. Photo courtesy of Queen Anne’s County Tourism. By Jay Fleming.

Take Terrapin Nature Park, which is oddly tucked behind an office park. It features extensive walking trails—complete with beach access, bridge views, a picnic area with grills, and tall grasses that sway peacefully in the breeze. Here, cyclists can pick up the Cross Island Trail, which stretches eastward through a section of the former Queen Anne’s Railroad rail bed, or the South Island Trail, which runs north to south along Route 8, past several parks and a golf course, ending up at Romancoke Pier near the island’s southern tip.


Hidden within the Chesapeake Bay Business Park itself are two other highlights. A 90-minute factory tour of Paul Reed Smith Guitars starts in the wood room, which is loud and fragrant, with industrial saws and machinery transforming wood varieties from all over the world into handcrafted instruments. You can watch the different stages of the process from start to finish.

Paul Reed Smith Guitars shows how its instruments are crafted through factory tours. Photo courtesy of Paul Reed Smith Guitars.

Not far from Paul Reed Smith Guitars is Blackwater Distilling, which conducts tours and offers samples of rum and vodka daily.

In the town of Stevensville, which sits about 10 minutes north of Route 50/301, you’ll find some of the island’s oldest structures. There’s a cemetery that dates back to 1652, the Historic Christ Church that was built in 1880 and the gabled Cray House, erected in 1809 as a tradesman’s home. Many of these sites are open to the public on the first Saturday of each month from April through November.

What isn’t hidden, thankfully, is the water—and there are plenty of ways to get near it, on it and in it. Nature lovers will enjoy the Chesapeake Bay Environmental Center, a 510-acre wildlife preserve in nearby Grasonville that offers guided kayak tours, four miles of trails and an abundance of native flora and fauna among its woodlands, marshes and meadows.

Ferry Point Park. Photo courtesy of Ferry Point Park.

A trail behind the Chesapeake Heritage & Visitor Center leads to a secluded beach at Ferry Point Park, where kids can splash worry-free in the shallow, tranquil inlet. (Bring bug spray—the mosquitoes are aggressive.)

For sporting types, the island is a departure point for many charters, including Angler’s Connection Guide Service for finding the best fishing grounds; Narrow Escape Charters, which focuses on bow-fishing for stingrays; and Captain’s Pride Charters, which is run by a second-generation charter captain. There are also a handful of hunting outfits if you’re looking to hunt waterfowl, deer and small game.

And, of course, there’s seafood. Hopefully, you like crab—a ubiquitous offering in these parts. You’ll find crab dip, crab soup and crabcakes galore on just about every menu.

Kent Narrows boasts waterside dining options. Photo courtesy of Kent Narrows.

During warmer months, the nightlife at nearby Kent Narrows—the thin strip of land that sits just east of Kent Island, serving as a sort of connector to the mainland—heats up with live music, tiki bars and water-taxi barhopping. Or perhaps you’d prefer to end the day with a more low-key option such as a sunset cruise. Whatever you do, it should definitely involve gazing out upon that beautiful, abundant water.

Rina Rapuano is a freelance food, travel and lifestyle writer who lives in Washington, D.C. She’s on Instagram @rinacucina.


Kent Island

Map illustration by Laura Goode.

Where to Eat

Bridges Restaurant
Kent Narrows, an area just east of Kent Island, has a healthy cluster of popular bars and restaurants. This newer spot boasts its own dock so boaters can “dock and dine,” but it’s also accessible by car. Watch locals pull fish out of the water while you savor a watermelon-feta salad, fish and chips or yet another scrumptious crabcake.

Knoxie’s Table
This cozy restaurant at the Inn at the Chesapeake Bay Beach Club channels urban chic but still fits with the low-key vibe of the island. The kitchen plucks ingredients from the chef’s garden for its seasonal menu—but the outstanding fried oysters, biscuits and cream-of-crab soup are always in season.

The Narrows
With a backdrop of boats, birds and sunsets, this decades-old local favorite in Kent Narrows is known for its crabcakes and cream-of-crab soup. It’s right on the water.

Rustico Restaurant & Wine Bar 
The menu at this beloved Italian spot is pretty heavy on seafood, but would you want it any other way? If you’ve had your fill of crabcakes, try the fried calamari, the Caprese salad or the penne with fresh mozzarella, tomatoes and marinara sauce.


Where to Stay

The Inn at the Chesapeake Bay Beach Club
With plenty of outdoor space that includes beach access, a terrace with a large fire pit and a culinary garden, this modern inn will add three shallow dipping pools this spring. Prices range from $289–$589.

Kent Manor Inn
This gorgeous waterfront inn, surrounded by 220 acres, dates back to the 1820s and offers kayaking, lawn games, 24 rooms (some with balconies) and a popular Sunday brunch. Rates range from $200–$329.

Maria’s Love Point
You’ll find personal touches, such as comfy couches near a wood stove, at this four-room B&B, which features a pool and the scenic Chester River out back. Rooms go for $179–$272.


Where to Sip

Blackwater Distilling
The award-winning rum and vodka distillery runs hourly tours and tastings from noon–4 p.m. daily for $5 per person. Don’t miss the dark rum and the coffee liqueur.

Cascia Vineyards
It’s tough to believe this relatively small island actually houses a vineyard, yet there it is at the end of a peninsula, about 10 minutes from the foot of the Bay Bridge. Stop in and grab a few bottles on the way to the beach (we recommend the Nebbiolo, Viognier and Norton varieties).



Spring Fling Car Show—May 5
This family-friendly affair is put on each year by the Kent Island Cruisers, a club for classic car enthusiasts.

Kent Island Day—May 19
Locals celebrate the 1631 founding of Kent Island with a parade, historic exhibits, activities, food and vendors.

Family Movie Nights
Free kid-friendly movies are screened Saturday evenings from May through September in various Queen Anne’s County parks.

For more information on upcoming events, visit the Queen Anne’s County website at