11 Cutest Small Towns In Chesapeake Bay For 2025

Every year, vacationers flock to the seaside hub of Cape Cod up north or the many beach towns of coastal Florida in the south. But have you ever considered that there might be a lesser-known gem sitting almost exactly halfway between? The Chesapeake Bay is as rich in history, seaside relaxation, and good food as any of those more popular destinations, with much smalller crowds, if any at all. If that sounds like your kind of summer retreat, these 11 Chesapeake Bay towns are as cute as they come.

Cambridge, MD

Established way back in 1684, Cambridge is one of the oldest European settlements in the U.S., and its attractions and charm more than live up to that rich history. Itching to get out in nature? The nearby Blackwater National Wildlife Refuge is one of the most important bird habitats on the East Coast, and it’s a hiking and kayaking destination par excellence. Looking for a bit more excitement? Visitors in May or July will be able to cheer on the town’s two major powerboat racing events. Want a touch of luxury? Golf, biking, and boating are only a few of the attractions on offer at the Hyatt Regency Chesapeake Bay.

Or maybe you’re more interested in history, in which case you should make a stop at the visitor center before heading out on the Harriet Tubman Underground Railroad Scenic Byway, which begins in Cambridge and follows the secret network used by enslaved people in their flight northward to freedom. Of course, taking the time to relax and enjoy the peaceful atmosphere of this storied seaside town is just as much of a must-do!

Cape Charles, VA

If you’re looking for white-sand beaches without the expense or crowds of a weekend in Florida, Cape Charles is a fabulous option. A member of the Virginia Main Street Program with a focus on revitalizing and preserving historic towns and promoting economic development, Cape Charles combines beachfront relaxation with manicured charm.

But before this area became as vibrant and diverse as it is today, fishing was its mainstay. Cape Charles Town Harbor has long been a launching point for fishing boats, and you can either take a boat out yourself to catch some of the area’s famous crab or simply watch the experts unload their catch at the harbor. Perhaps, after that, a stop at the Cape Charles Museum to learn about the area’s maritime industries would be in order. Then, sample that crab at A1 Seafood, one of the town’s best purveyors of the shellfish for which this area is world-famous.

Chesapeake City, MD

Water is the lifeblood of this region, but that’s especially true in Chesapeake City. Its C&D Canal, which connects the Chesapeake and Delaware bays, is one of the world’s busiest. Though that may sound more industrial than tourist destination, a visit to the C&D Canal Museum will explain why this town’s unusual infrastructure is not only of vital commercial importance, but fascinating. For a bit of exercise, you can follow the canal yourself by foot or bike on the Ben Cardin C&D Canal Recreational Trail. Oh, and the town itself is on the National Register of Historic Places for its 19th-century downtown, so be sure to check out the antique shops, cafes, galleries and boutiques in the walkable Chesapeake City Historic District.

Crisfield, MD

The self-proclaimed “Crab Capital of the World” takes its seafood very, very seriously. Every season of the year has a crab-themed community event, and you can find a place to sample Chesapeake Blue Crab year-round. Take a Labor Day weekend trip to attend the National Hard Crab Derby, a unique and lively festival that includes crab races, picking contests, a beauty pagent, parades, fireworks, and, of course, lots of delicious food.

The original Ward Brothers Workshop showcases another quirky local industry with its display of tools and equipment for duck decoy carving, an under-appreciated art. Those looking to get out on the water themselves might fancy a boat cruise to Smith Island. Or, you can catch yourself a DIY crab dinner by “chicken necking.” This simple, low-cost crab fishing technique using a chicken neck as bait may be a little bit outside of your comfort zone, but the cherished local tradition is by far the cheapest and most innovative way to get yourself a delectable crab dinner!

Easton, MD

The towns of Easton, Oxford, and St. Michaels are often visited together, thanks to their proximity, but each town more than stands on its own. In Easton, you’ll find the best cycling opportunities of the three; with 38 miles of waterfront vistas, a ride along the Chesapeake Views Trail could easily take a whole day. Easton was also the hometown of abolitionist Frederick Douglass, and he’s commemorated with a self-guided Frederick Douglass Driving Tour beginning in Easton. Culture vultures, meanwhile, will enjoy a show at the beautifully-restored Avalon Theater, and autumn visitors will get to enjoy the annual Waterfowl Festival held over three days in November. Ever wanted to hear a master duck caller do their thing? Here’s your chance.

Havre de Grace, MD

Though each of these Chesapeake Bay towns is deeply connected to the Bay, Havre de Grace stands out as a waterfront town in the truest sense of the word. Its major industries are fishing and carving duck decoys. Experience one at the Havre de Grace Decoy Museum and the other at Water Street Seafood. Visit Havre de Grace Maritime Museum to get a hands-on look at the town’s ties to the water. In addition to learning from its extensive exhibits, you can volunteer to assist in building a fishing boat in the traditional Chesapeake Bay style. Finally, you can’t leave Havre de Grace without snapping a picture of the town’s most iconic landmark, the Concord Point Lighthouse, a local point of pride that you’ll see in almost every photo of the town.

Kent Narrows, MD

Set a little ways back from the bay on the Kent Narrows inlet, this town’s quiet charm makes it perfect for visitors looking for a more relaxed locale than some of the busier towns on this list. Sampling the local crab catch at Harris Crab House (try the Nutty Buddy ice cream), biking the Cross Island Trail, or visiting the Chesapeake Heritage and Visitors Center for some background on this peaceful community are all excellent ways to get oriented in Kent Narrows. And if your idea of relaxation involves a little more time in nature, the Chesapeake Bay Environmental Center offers outdoor recreation opportunities, guided tours, close encounters with birds of prey, and the annual Eastern Shore Sea Glass and Coastal Arts Festival.

North East, MD

Another great pick for nature lovers, North East is best known for its proximity to the lovely Elk Neck State Park. There, you’ll find places to hike, bike, view the fall colors, and check out the iconic Turkey Point Lighthouse. It’s located just outside of North East, and a visitor to the town could easily fill several days with outdoor activities in the area.

But, like most towns around here, North East also has a very long and very well-preserved history. It’s home to an old-fashioned Main Street where you’ll find one of the oldest churches in Maryland, St. Mary Anne’s Episcopal Church. It’s also home to one of the state’s few covered bridges, and its longest. Gilpin’s Falls Covered Bridge was built in 1860 and spans 119 feet, and it’s a charming relic of old-time North East that you won’t find elsewhere.

Oxford, MD

Don’t make the mistake of assuming this second town on the St. Michaels, Easton, and Oxford itinerary is identical to its partners. Each offers history, scenery, and points of interest all its own. For one, Oxford has got one of the top five ice cream shops in the U.S. with the Scottish Highland Creamery. For another, the Robert Morris Inn 1710 is not only America’s oldest full-service inn, but the childhood home of a Declaration of Independence signatory. And if you’re a little more outdoorsy, the 29-mile Oxford/St. Michaels Bike Trail will take you through some of the most noteworthy historical sites in the towns of Oxford and St. Michaels — look out for the oak tree that accidentally became cannon fodder during the War of 1812 and is still holding onto that cannon ball today.

St. Michaels, MD

The final point of the St. Michaels-Easton-Oxford triangle, St. Michaels is home to more history and charm than you could shake a stick at. The Inn at Perry Cabin offers colonial architecture and manicured lawns perfect for watching the sailboats on the Miles River, and the ideal spot for a weekend stay. Golfers will want to take advantage of the Links at Perry Cabin, one of the Mid-Atlantic’s top competitive golf courses. And St. Michaels is also home to the Chesapeake Bay Maritime Museum, a regional center for learning about the region's long and fascinating ties to the sea. More interested in land-based transportation? No problem. The Classic Motor Museum makes for an equally fascinating pit stop.

Yorktown, VA

History buffs will know Yorktown as the site of the last major battle of the American Revolution, so it’s unsurprising that the American Revolution Museum at Yorktown is located here. That’s not all the history this town has to offer, though; the Jamestown Settlement recreates one of the earliest British settlements in the US through museum exhibits and an open-air recreation of the original colony. Unsurprisingly for such a historic city, Yorktown is a great place to take a ghost tour, which you can do with Yorktown Ghost Walks. Finally, get out on the water with Yorktown Sailing Charters for a different view of this winsome Chesapeake Bay town.

Whether you’re most interested in dining, history, or outdoor recreation, the Chesapeake Bay is a well-kept secret with top-of-the-line offerings in all of those areas and more. It’s a region that is in many ways perfectly set up for tourists, but rarely overrun with them. So if you’re looking for a new corner of the US to explore before it becomes trendy enough to bring in the crowds, why not book a flight to Baltimore or Norfolk and make your way down to the Chesapeake Bay?