8 Best Waterfront Communities in Maryland

Maryland’s historic maritime communities are an escape from the packed Mid-Atlantic metros. Whether on the mainland or the Eastern Shore, visitors come from Washington, DC, Baltimore, and Philadelphia to relax. A trip to Maryland’s waterfront is a literal breath of fresh air after all that congestion. But why visit the bay when you can live in one of these laid-back towns? Your slice of heaven awaits along the Chesapeake Bay waterfront.

We’re sticking only with Maryland communities for our list of best Chesapeake Bay towns. We skipped over larger Annapolis and Baltimore and excluded riverfront towns like Chesapeake City or Chestertown. All these towns access the Bay, creating a more ocean-like lifestyle. They frame the Eastern Shore, the slice of the Delmarva Peninsula facing inland, or sit on one of the other peninsulas.

Solomons

Population: 2,400

Location: Calvert County, Calvert Peninsula

Where the Patuxent River meets the Chesapeake Bay lies the laidback Solomons Village. Being on the mainland–also known as the Western Shore–gives residents more direct access to Washington, DC. But this bayfront shipbuilding community is worlds away from the congested highways. Relax each day with riverside walks on the Boardwalk. Or, watch the aircraft take off from the two nearby naval air stations.

Living close to at least four major parks is a serious perk. Some put a day at Calvert Cliffs State Park on their Maryland bucket list. Massive namesake cliffs dominate the shoreline. Visit to hunt the sandy beach and cliffs for fossils of long-gone whales, sting rays, and sharks. Just make sure you keep your hunting to designated zones, as the sandy cliffs are prone to collapse.

You don’t need to go far to live abundantly in Solomons. Just a boat is all you need. Cruise on the river on your craft or rent one from the marinas around town. Locals stay connected to the waterfront with fishing, sailing, and power sports. No matter your speed, end a day well spent watching the light fade over the waterfront from a restaurant or bar.

As a local, you’ll feel safe and cared for in a community that still looks out for its people. This is the kind of hamlet where the neighbors know each others’ names. They also love a good time. Locals put on quite the Fourth of July show for a small town. The community puts its best foot forward at the annual Taste of Solomons and Annmarie Sculpture Garden arts festivals. 

Havre de Grace

Population: 2,400

Location: Hartford County, northern Chesapeake Bay

The name means “State of Grace,” and that’s the vibe of this small town built where the Susquehanna River meets the Bay. It has received less attention than other Maryland waterfront communities, but that could change. Coastal Living featured it in 2023 as one of the best places to live on the coast. Now could be your chance to get into something special.

Havre de Grace is morphing its former industrial waterfront into a living shoreline. Now it has bobbing sailboats moored in marinas and a near-mile-long bayfront promenade. Locals have at least seven marinas and public boat ramps to access the excellent fishing and water sports. Its scenic Concord Point Lighthouse rises above it all. 

In another perk, the town has been designated one of Maryland’s Arts & Entertainment districts. Admire bronze-size sculptures, expansive murals, and more around town at the Graw Alley Art Park. For more local culture, the local Tideway Players put on stage performances throughout the year. Locals come out for the First Friday street fairs and the summer concert in the park series. 

There are still more ways to enjoy life here. Havre de Grace has a golf course, tennis courts, pickleball courts, and a winery. The recurring Farmers Market comes downtown every Saturday. So be up at sunrise to fish, browse fresh-picked produce mid-morning, and sip away the afternoon with a local glass of vino. 

Next to the waterfront, the historic town’s brick buildings hint at its wealthy 19th-century heyday. Be assured that the cafes and nautical gift shops inside are thoroughly modern.

Oxford

Population: 608 

Location: Talbot County, Eastern Shore

A small town at the mouth of the Tred Avon River, Oxford is tiny but mighty. The historic colonial port town has a timeless architecture that visitors love about the Eastern Shore. Its waterfront property varies between sandy stretches and sailboat-dotted marinas. Craft of various sizes fit into its harbors. 

The waterfront is central to the quiet Oxford lifestyle and has been since its 1694 founding. The Oxford-Bellevue Ferry is the nation’s oldest privately owned ferry service. Its Tred Avon Yacht Club is approaching a century in age. 

Strolling around the brick-paved sidewalks feels like classic Americana. White picket fences do exist, and the commercial hotel strips are nearly non-existent. That’s just how Oxford locals like it: low-key and without glitzy waterfront condos. Bed-and-breakfasts and inns are in historic colonial-style buildings, not name-brand concrete block hotels.

Its relaxed downtown area lures tourists. The shops cater to the crowd with local jewelry, nautical-themed attire, gifts, and antiques. Some visitors motor into the harbor to visit the waterfront restaurants. A good day in Oxford, MD, ends with the crack of oyster shells and boiled crabs. The fresh-churned ice cream is the cherry on top of a perfect day.

Oxford falls within 90 miles of Baltimore, Washington, DC, and Annapolis. The upside to having a tourist industry is access to more dining and nightlife than you’d have in a small bayfront town otherwise. Many residents commute to work because it is a small town. 

Easton

Population: 17,000

Location: Talbot County, Eastern Shore

The stars are rising on Easton, one of Eastern Shore’s larger towns. Brimming with Victorian charm between its historic homes and bricked streets, it feels more European than a quiet American bayfront town. The buildings have been beautifully and lovingly preserved. Inside them are new restaurants that are making Easton a food destination.  

It’s a great place to live if you like the arts. Art studios dot the downtown center. Avalon Theater draws Eastern Shore residents for stage shows and live music. Even more come for the annual Plein Air Painting Competition. If you see a lot of ducks and water birds, don’t be surprised. Easton hosts the world decoy contest. Birding is a popular activity and another reason why people visit Easton.

The lively arts community caters to visitors and locals. Head downtown for First Night Talbot or Easton Outdoor Movie Nights. The Chesapeake Fire & Ice Festival is definitely unique, a popular February street fair. Ice sculptures are all over town, and there’s an outdoor ice skating rink. 

Waterfront homes for sale are found on the Tred Avon and Miles Rivers. To the west of town is the winding Choptank River. All will take you to the Chesapeake Bay. 

Tilghman Island

Population: 830

Location: Talbot County, Eastern Shore

You can have a more authentic maritime lifestyle on Tilghman Island. This watermen’s village is a working one, with a commercial sailing fleet bringing in fresh catches every day. Water surrounds it on three sides as it juts deep out into the Bay. Knapps Narrows cuts it off from the mainland. 

Tilghman Island could be up your alley if you like living off the beaten path. Crowds come for the blue crab feasts and water contests but disperse between events. That leaves locals with endless waterfront views and quiet evenings. Ditch the car for a bike or, even better–a boat. The pace is chill, with locals running on island time. 

The island’s small population fosters a strong sense of community and belonging. Neighbors know each other by name and look out for one another. Expect to be greeted by name when out walking the dog or heading down to the bayfront. And those sunset views from your waterfront home–spectacular!

Cambridge

Population: 14,000

Location: Dorchester County, Eastern Shore

Eastern Shore visitors often make Cambridge their jumping-off point for all the region’s treasures. Its attractions include a waterfront resort with a golf course Condé Nast ranked as one of the top northern US golf resorts. Two museums pay homage to Cambridge’s History. Learn about local heroes like Harriet Tubman or its four-century-old maritime history. Kids love the nautical-themed playground at Sailwinds Park.

Main Street Cambridge is a thriving downtown center. It has all you’d expect of a Maryland tourist town: antique shops, art galleries, and eclectic gift stores. The seafood joints serve steamed blue crabs and Old Bay along the waterfront harbors. Visit the taverns and pubs for a more chill afternoon. Art installations and murals on the old buildings pay homage to Cambridge’s nautical connections. It’s just an excellent place to walk around and the center of town life. 

The town’s culture is very active. First, there are the boat races on the Bay. Boats have thundered down the Choptank River in the nation’s largest powerboat race for over a century. The town also hosts two Ironman Events, including Ironman Maryland. A growing craft brewing scene is one sign of its increasing culinary offerings. 

Another top attraction from Cambridge is the sprawling Blackwater National Wildlife Refuge, which is out the town’s back door. The park on the Great Atlantic Flyway is a favorite for birdwatching and for escaping on quiet paddle craft into the wetlands. 

The town rests at the Choptank River mouth, right off Highway 50. This makes traveling around the Eastern Shore, including to Ocean City, more convenient. 

St Michaels

Population: 1,000

Location: Talbot County, Eastern Shore

Picture a Maryland Eastern Shore town in your mind. Chances are, your image matches St. Michaels. The town view is a horizon of salt-washed marinas and boardwalks, bobbing masts in the harbor, and the screw-pile Hooper Strait Light. On land are ornate Victorian homes with stately front porches and turreted roofs. It’s this colonial seaside character that helped St. Michaels earn a spot in USA Today’s Best Small Coastal Towns.

St. Michaels sits on a peninsula, with most of the town facing the mouth of Miles River. Inlets to Broad Creek are on the backside. All that perfect waterfront gives St. Michaels three in-town marinas and access to fresh Chesapeake Bay seafood. Bay breezes waft through town, adding to its chill coastal ambiance.

Its B&Bs and eclectic boutiques attract many tourists because of their scenic views. Some are stately old manors directly on the waterfront. The tourists visit attractions like the Chesapeake Bay Maritime Museum. The 18-acre facility feels like one one-part park and one one-part history. The legendary Perry Cabin golf course has Chesapeake Bay views. Harbor cruises, wineries, and antique stores in the walkable downtown add to reasons why so many enjoy St. Michaels. 

As a place to live, you’ll thrive in a tight-knit community. St. Michaels Community Center runs programs for all ages. There’s a YMCA branch that provides fitness and social activities. The 11 local parks include a community garden, a sports complex, and a nature preserve. A farmer’s market comes to Talbot Street from April to November and sells local produce. Many of its iconic waterfront homes come with private docks for motor boats and yachts. 

Waterfront Living in Maryland

Maryland’s waterfront communities stand out for their scenic beauty and coastal living charms. With yachts, fresh seafood, and friendly people, it’s easy to see why so many escape to the Bayshore towns each year. The state does have over 3,000 miles of shoreline, after all. These top waterfront communities are the start of what could be your path to the lifestyle you’ve always dreamed of. Explore more about moving to Maryland with a local real estate agent.