Maryland's Charming Island Town Has Laid-Back Marinas, Great Restaurants, And Chesapeake Bay Beauty

Annapolis may be known as one of America's prettiest cities, but there's a small town less than half-an-hour away that's bursting with charm of its own. Nestled on Kent Island, the Chesapeake Bay's largest island, Stevensville is a waterfront escape that's home to tranquil marina and Chesapeake Bay scenery, a vibrant downtown, and an exciting restaurant scene — everything you could ever want from a relaxing getaway. 

Stay at The Inn at the Chesapeake Bay Beach Club for an unforgettable Kent Island vacation. With sweeping garden and Chesapeake Bay views, numerous dining options (including one of the best restaurants in town, Knoxie's Table), a spa, cozy fire pits, heated pools, a fitness center, and more; a stay at The Inn is nothing short of luxurious. Make it a stop along the "All-American" scenic byway on Maryland's shores or stay for a quick weekend. Either way, Stevensville is Maryland's idyllic island town you've probably been overlooking.

From walking along Stevensville's laid-back marinas to exploring its charming historic downtown, Stevensville is one of best of Maryland's many quaint towns with coastal charm. After its founding in 1850, Stevensville prospered as a base for Chesapeake Bay steamboat travel, and you'll still find reminders of its heyday there. Stevensville's downtown is brimming with historic spots, from a 19th-century train station to an old-timey post office which dates back to the mid-1800s. Its historic sites are open to the public between May and November for a few hours on the first Saturday of each month. Otherwise, you can enjoy checking them out from the outside on a self-guided walking tour. Stevensville's downtown also has a designated arts and entertainment district, so be sure to pop into the Kent Island Federation of Art while you're here, an exhibition space for local artists that's been open since the '60s.

In Stevensville, there's no shortage of nature or amazing scenery. For Chesapeake Bay Bridge views, head to the 276-acre Terrapin Nature Park. Within the nature preserve, walk through ethereal wildflower meadows, venture across coastline dotted with tidal pools, and explore peaceful woodlands. Beachgoers should venture to Matapeake Beach and Clubhouse where you'll find a public beach as well as a dog beach.

Stevensville's dining scene has tons to offer foodies, especially for anyone looking for dinner with a view and local seafood. Escape to Italy at Amalfi Coast Italian and Wine Bar, one of Stevensville's top eateries, beloved for its mouthwatering seafood and pasta dishes. And you know you can't leave Kent Island without trying some fresh Chesapeake Bay seafood. Libbey's Coastal Kitchen and Cocktails, located at Bay Bridge Marina, is a must while in Stevensville to enjoy local seafood alongside gorgeous Chesapeake Bay scenery. You can't go wrong with Stevensville institution Kentmorr Restaurant and Crab House, either. With roots tracing back to the 1950s, this gem serves up fresh Maryland seafood, local craft beer, and handcrafted cocktails in its indoor dining rooms, outdoor deck seating, and seasonal beachside tiki bar.

Knoxie's Table at Chesapeake Bay Beach Club is one of Kent Island's top restaurants, with a focus on sustainable, farm-to-table cuisine, including fresh seafood and straight-from-the-garden ingredients. The restaurant also features weekly whiskey and wine specials and on Thursday evenings you can catch some live music. Stevensville also has its very own winery, Cascia Vineyards and Winery, which opens its tasting room on weekends from noon to 4 p.m.