Forget Annapolis — Maryland's Under-The-Radar Island Is Known For Seafood And Coastal Trails

Considered one of America's prettiest cities thanks to its old town Europe vibes, Annapolis in Maryland has always attracted visitors aching to sail the Chesapeake and enjoy charming architecture. But if you're looking for spellbinding coastlines, not to mention excellent seafood, without the Annapolis crowds, look no further than Kent Island. Vastly overlooked in favor of its more popular neighbor across the water, Kent Island is wedged within the Chesapeake Bay, offering visitors a welcome escape full of seaside views, relaxing beaches, and tasty eats.

Once inhabited by the Algonquin tribe, the first Europeans arrived on Kent Island in the 1630s, where they established a fortified settlement with a trading post and courthouse. Today, a visit to Kent Island will be punctuated by seaside strolls amidst coastal cottages and relaxed sips in cozy wineries. Head to historic Stevensville to spend the day exploring the enchanting downtown district, registered as a National Historic Place. Charter a fishing boat down at Kentmorr Marina for a spectacular day out with the family on the Chesapeake, or explore the picturesque walking trails through coastal wetlands within the Blue Heron Nature Preserve.

Exciting events in the community calendar make Kent Island worth a visit all year long. The streets of downtown Stevensville erupt into excitement each May with parades and lively entertainment in honor of Kent Island Day, which celebrates the founding of the island almost 400 years ago. Meanwhile, stop by in October for the annual Artoberfest event and browse the unique handicrafts from local artisans. Given its location only about 45 minutes from Baltimore/Washington International Airport (BWI) or an hour from downtown Baltimore itself, Kent Island is a hidden waterfront gem that's easy to get to.

The first order of business on any island getaway is a trip to the beach, so head to the Matapeake Clubhouse and Public Beach to find a sandy spot for lounging. Cool off with a refreshing swim in the bay, or enjoy a picnic with the family. If you have furry friends with you, a small portion of the public beach is sectioned off for pups to splash around. Anglers looking to cast a line should head to Matapeake Pier just down the road, which boasts floodlights so the fishing day doesn't have to end even after dark. 

At the Terrapin Nature Park north of the island, you'll find almost 300 acres of scenic coastal and forested landscapes to explore. A long stretch of sandy beach is perfect for enjoying a quiet moment to yourself, while winding coastal trails offer scenic panoramas of the Chesapeake Bay. The surrounding shady trees and meadows vibrant with wildflowers are home to wildlife, especially various types of birds, so make sure to keep your eyes peeled as you head out for a hike. Stay until sunset to snap memorable photos and bask in unforgettable views.

If you have kayaks with you, bring them to the launch at Romancoke Pier on the southeast side of the island. Paddling around the Eastern Bay can be a thrilling adventure. Visitors can also relax at the nearby picnic area while anglers head out to catch crabs and fish. For more seafood adventures, head down to Crisfield, an underrated Maryland fishing city known as the crab capital of the world, a few hours south but still on the Eastern Shore of the Chesapeake Bay.

A day spent playing in the Chesapeake will leave you feeling peckish. Whether you're looking for a relaxed beach bar, a quaint pub, or an upscale dining atmosphere, Kent Island has it all. Highly-rated on Tripadvisor is the Kentmorr Beach Bar & Grill, which serves up a mix of refined seafood appetizers along with pizzas, salads, and sandwiches. Sit down with the family in the rustic interior dining space, or dip your toes in the sand and sip refreshing cocktails at the beach tiki bar. A previous guest declared it to be "one of the most memorable places you'll visit" in a Google review. 

At the island's northernmost tip is the Love Point Vineyards and Winery, where lawn chairs facing the bay offer a picturesque setting for wine tastings. Pair your glass with a charcuterie board and bask in the romantic coastal atmosphere. For a more intimate vibe with live music on the weekends, try the Pour House Pub. The Pour House offers a selection of tasty cocktails, weekly specials, and hearty pub grub.

Extend your adventures in Kent Island by spending the night at a cozy coastal cottage. Boasting a perfect five stars on Google is the Blue Heron Landing, a dreamy white Colonial-style bed and breakfast with an impressive colonnaded façade overlooking the sprawling lawn. Maria's Love Point Bed & Breakfast is another option just a short drive from the winery, boasting spacious bedrooms and a secluded porch. Your thrilling Maryland adventures don't have to end there, either. The Chesapeake Bay is the world's largest natural watershed and worth exploring in-depth. Just a 40-minute drive north brings you to Chestertown, offering annual festivals and fresh Chesapeake Bay seafood.