Maryland’s largest island is an underrated gem in the Chesapeake Bay

On the Chesapeake Bay, 20 miles east of Maryland’s capital, Kent Island is a town known for its sprawling waterscapes, scrumptious seafood, and storied maritime history. Despite its many superlatives, this bayside city doesn’t receive the attention it deserves like nearby Annapolis and Ocean City. 

Although viewed as a gateway to Maryland’s Eastern Shore, Kent Island is more than a scenic pitstop. The area’s history has intertwined with the birth of America, when Captain John Smith, who famously helped establish America’s first settlement, Jamestown, declared in his 1608 journal entry, “Heaven and earth never agreed better to frame a place for man’s habitation…” More than two decades later, Kent Island, the largest island in the bay, was established, making it the third-oldest English settlement in the U.S. 

The allure of Kent Island, Md., still lives up to Captain Smith’s praise today. Yet this underrated island continues to deliver the sights and experiences that draw people to Maryland. Here are 10 things every traveler should experience when visiting Kent Island.

1. Explore the region by boat

Visitors can explore Kent Island from the water because it lies in the largest estuary in the U.S. You can enjoy unencumbered views of the bay and Bay Bridge and see the natural curves of the island’s shorelines as you drift along the island’s coves, inlets, and marshes. The word Chesapeake is an Algonquian word meaning ‘great shellfish bay.’ The brackish water of the bay is indeed a breeding ground for a host of life, which has been the lifeblood of the local economy, cuisine, and culture for the last century. This region is a working waterfront; it’s common to see vessels slicing up and down Kent Narrows, the waterway that separates Kent Island from the nearby mainland.

Charter a boat and spend a day fishing, crabbing, or oystering. Or glide through the picturesque waters to watch as the sun dips below the horizon aboard a sunset cruise.

2. Learn about local wildlife

The Chesapeake Bay watershed is home to more than 3,600 species of plants and animals, including striped bass (also known as rockfish) and 173 species of shellfish. Observe local wildlife at the Chesapeake Bay Environmental Center, where you can hike, bike, or kayak through this 510-acre nature preserve, which includes forests, wetlands, tidal marshes, and meadows. Avid birdwatchers will find this center ideal. Throughout the year, they can spot more than 240 bird species, including bald eagles, ospreys, and herons. In addition to avian spotting, visitors may catch a glimpse of otters, muskrats, foxes, and diamondback terrapins found throughout the preserve. 

3. Explore the region’s beaches

You won’t have any issues finding a beach in this coastal city. Head in any direction, and you will eventually stumble upon the shoreline. For the best swimming areas and scenic views, visit  Matapeake Clubhouse and Public Beach, which has an outdoor amphitheater, family picnic area, and dog beach, or stretch out on the soft, caramel-colored sand at Terrapin Nature Park and Beach, which boasts unobstructed views of the Bay Bridge.

4. Cycle across the entire island

Pedal or walk your way across the island by following the Cross Island Trail. The mapped path spans nearly seven miles, covering the width of the island, and snakes through tidal wetlands, shady woodlands, and wide-open meadows. The paved trail begins at Terrapin Nature Park and Beach on the island’s western shore and winds eastward to Kent Narrows. Both cyclists and hikers can enjoy views of the Chesapeake Bay along the trek.

5. Get a lesson in African American maritime history

Niambi Davis, a freelance writer and community historian at Kennard African American Cultural Center, grew up in the area more than 70 years ago. She recalls, “We were called the land of pleasant living, and we still are in terms of recognizing and reckoning with our history.”

Her reflection emphasizes the importance of preserving community memories—a mission that organizations dedicated to sharing and safeguarding these stories continue to pursue. The Kennard African American Cultural Center offers a meaningful view into the Chesapeake’s history. Situated about 20 miles east of the island in the historic Kennard High School, which was the first secondary school for African Americans in Queen Anne’s County. Through oral stories, exhibits, and educational programs, the museum preserves the histories of Black watermen, oyster shuckers, and maritime workers.

Visitors can learn about people such as Captain Eldridge Meredith, a longtime member of the Eastern Shore waterman community. Watermen are typically independent shellfish harvesters and fishermen who make a living from catching and selling blue crabs, oysters, and other fish found in the Chesapeake Bay. These people generally work alone or in small groups. The captain spent over 70 years working as a fisherman and, in his later years, became a head boat captain, taking patrons out for sightseeing, crabbing, or oystering cruises. “He was the patriarch of a dynasty. Today, his son Captain Tyrone Meredith and daughter Captain Vera Meredith are carrying on his tradition,” says Davis. 

(Secrets of Harriet Tubman’s life are being revealed 100 years later)

6. Step back in time in Stevensville Historic District

Continue your history lesson with a stroll through the Stevensville Historic District. Listed on the National Register of Historic Places, this walkable area is a time capsule catapulting visitors back to the late 19th century. Beautifully preserved historic buildings that line the streets tell the story of the island as one of Maryland’s and America’s earliest settlements. Tour the centuries-old Cray House (Stevensville’s oldest house), the Stevensville Train Station (1902), and the Old Stevensville Post Office restored to its 1877 glory.

“I would recommend visitors try to come on the first Saturday of the month from April through November,” says John “Jack” Broderick, the president of the Kent Island Heritage Society. “All the historic sites are open. You can walk in Stevensville today and get a feel of what it would’ve been like 100 years ago.”

7. Indulge in a Classic Maryland Crab Feast

Partake in a quintessential Maryland experience—the crab feast. In this timeless tradition, friends and family gather around a paper-covered table, armed with wooden mallets to crack open bushels of freshly steamed Maryland blue crabs seasoned with Old Bay. These crabs are then dipped into melted butter and washed down with a frothy, cold beer. 

“Crabs are a big part of life on Kent Island,” says Broderick. “Anybody who lives on the water or has a relative on the water generally has crab pots. Or you can go out to one of the great crab houses and sit down for a terrific crab feast.”

8. Dine on the catch of the day

With its location in Chesapeake Bay, Kent Island has no shortage of standout seafood restaurants. Harris Crab House, one of the last year-round oyster processing houses, is a local institution. On the restaurant’s menu, the Eastern Shore Tower is a feast of fried soft-shell crab, lump crab meat, and oysters piled high. While here, don’t miss the chance to check out the mural along the walls of the processing building, which depicts the history of the business.

Libbey’s Coastal Kitchen + Cocktails is another popular dockside spot that draws crowds with dishes like their crab cake platter and jumbo lump crab pizza. Bridges Restaurant also impresses with its soft crab and seafood club sandwiches.

9. Savor the taste at local wineries

Oenophiles can savor the taste of local wines at three vineyards. The Chesapeake Wine Trail has two along its route: Cascia Vineyards & Winery, a family-run business popular for its award-winning Queen Anne’s Reserve (a Bordeaux-style blend), and Love Point Vineyards & Winery, launched by a husband-and-wife team, where guests can sample flight tastings of red and white wines while taking in stunning views of the Chester River. Their most popular red is the Bloody Point Light, which is a hybrid pinot noir named after the lighthouse on the southern tip of the island. The third winery is the Chesapeake Manor Vineyard. Visitors can select from their award-winning 2023 inaugural vintage, which includes a Grüner Veltliner, a white wine that’s a favorite with patrons. 

10. Join the festivities on the Bay

Kent Island hosts festivals throughout the year. April starts with the Bay Bridge Boat Show, followed by Kent Island Day in May. During the summer, there’s the Bikes and Beer Festival in July and the Sudlersville Peach Festival in August. As summer slips into fall, the art-centric event Artoberfest is in October, the Bay Bridge Run is in November, and the year closes out with the Waterman’s Crab Basket Tree Lighting.

Where to stay

For a noteworthy escape on Kent Island, check into the Inn at the Chesapeake Beach Club. The hotel has 77 well-appointed guest rooms and suites, an on-site restaurant, and a spa. Guests can't beat the hotel’s location near the Chesapeake Bay, as well as waterfront restaurants and shops.