The Best Small Towns on the Chesapeake Bay to Chill Out In 2024

Once the most productive estuary in the United States and amongst the top five internationally, the Chesapeake Bay's contribution to the nation's historical foundation and its natural resources is unmatched. Home to twenty million people and over 3500 species of plants and animals, this Mid-Atlantic region is one of the top vacation destinations on the East Coast. It's relaxed and chilled vibe has made it popular getaway and its appeal continues to grow in 2024. Rooted in Native American culture, this region proudly reflects its European and Indigenous influences in its architecture and town names. From its expansive seaports to its cobblestone streets, visitors are immediately enchanted. Drop anchor and learn why author James A Michener found it the ideal muse.

Cambridge MD

This original colonial settlement, dating back to 1864, has a storied history. Settled along the Choptank River as a seaport community, its role as a maritime-centric hamlet is celebrated in its museums, architecture, and well-traversed cobblestone streets.

Main Street in the town center is described as one of the most beautiful in the country. Here, you will find quaint shops that pay homage to the town's diverse heritage.

The birthplace of the founder of the Underground Railroad, Harriet Tubman, honors this brave pioneer with an interactive museum and its storytelling mosaic murals throughout the town.

For the nautical enthusiast, visit the Richardson Maritime Museum or ride on one of their many sailing vessels with fully narrated guides.

Havre De Grace MD

In 1785, General Lafayette named this town after Le Havre, France, due to its striking similarity to their French seaport. It lives up to its name, "Harbor of Grace," with its pivotal role in America's continued fight for independence during the Revolutionary War.

Its desirable position between the Susquehanna River and the Chesapeake Bay made it a destination for fishermen and seamen. With significant exports of crabs and oysters, this port gave the area an economic boom for over two centuries.

Stroll on the promenade, and you will end up at the Friends-Concord Point Lighthouse. Built in 1827, it is the second oldest in Maryland. Regarded as the heart of Havre De Grace, it was fully operational until its decommission in the 1970s. Still open for public tours, it offers some of the most stunning views on the Chesapeake.

This town is replete with museums for all kinds of tastes. One of the quirkier venues is the Havre De Grace Decoy Museum. Over 1,200 different duck decoys are on display. Anasaphilians will learn more than they ever thought they needed about these artistically crafted waterfowl.

Book a room at one of their many historic B&Bs for an extended visit. Designed in 1896, the Spencer-Silver Mansion offers modern amenities without sacrificing its original Victorian design.

Urbanna, VA

The "City of Anne" is located in Middlesex County, Virginia. Named after Queen Anne of England, this minimally populated town has much to offer in terms of homespun charm.

Set on the Rappahannock River, Urbanna is known as the oyster capital of the state. The annual oyster festival further amplifies this status. Held every fall, this town of less than 500 residents welcomes over 70,000 visitors to celebrate this saltwater delicacy.

Hampstead Farm, built in 1750, is nestled on 100 acres of farmland. This white stucco wonder has been fully restored and was a frequent stopover for George Washington. Best of all, it is available to rent for short-term stays.

Yorktown, VA

It is best known as the spot where General Cornwallis surrendered to George Washington in 1781, essentially ending the Revolutionary War. Yorktown is one of the three sites of the historic triangle of the colonial settlements.

With a rich history, this hamlet offers many opportunities to walk in the footsteps of our founding fathers. Yorktown Battlefield is the site of Washington's 1781 victory over British Forces.

Close to both Jamestown and Williamsburg, Yorktown offers access to their busier counterparts but with the luxury of returning to a more chilled vibe.

Stroll into the town center to Grace Episcopal Church, built in 1697; it counts two of the original signers of the Declaration of Independence in its congregation.

The scenic Riverwalk blends history and the contemporary with quaint shopping and dining.

Cape Charles, VA

Pennsylvanian assemblyman William Lawrence Scott founded Cape Charles, which is on the National Historic Registry. One of the first planned communities, it was designated as a railway stop between Philadelphia and Norfolk.

The Ferry system that came a few years later only cemented it as a strong connection between the north and south industrial growth. With roots in fishing, Cape Charles was one of the largest exporters of oysters and clams on the East Coast.

The original Cape Charles Lighthouse, built in 1828, was the first lighthouse on the Chesapeake Bay in Virginia. It no longer exists; however, the current lighthouse, built in 1895, offers daily tours.

Cape Charles Coastal Habitat Natural Preserve spans 50 acres. This small but vital site maintains the beaches and surrounding marshes. Public access is limited to the boardwalk but offers stunning sunset views.

For the golf enthusiast, try a round on the 18-hole Bay Creek Golf Club course. Designed by the legendary Arnold Palmer, it has been the site of multiple international competitions.

Head to Strawberry Street for local shopping and dining, as well.

Saint Michael's, MD

In Talbot County, Saint Michael's is a sought-after vacation destination. Originally designated as a trading post for tobacco farmers, it became known as "the town that fooled England" during the War of 1812. A self-imposed blackout caused the British to miscalculate their cannon fire and miss almost all structures in the town.

Take a cruise on the Patriot. In operation since 1968, this double-decker vessel offers a 2-4 hour harbor tour. Fully narrated, it is the best way to get introduced to this historic town.

Shop for fresh produce and seafood at the St. Michaels Farmers Market. This non-profit, community-based market benefits local pantries and shelters.

The Chesapeake Bay Maritime Museum sits on 18 acres of waterfront property. Home to the Hooper Strait Lighthouse, its exhibits include the nation's most comprehensive collection of Chesapeake-based artifacts.

Indulge in a local favorite, Maryland crabcakes, at the Crab Claw Restaurant on Burns Street. Then, shop for locally crafted gifts on Talbot Street.

Ocean City, MD

Situated along the Atlantic Ocean coastline, Ocean City, Maryland, is known for its family-friendly community. It is a water lover's utopia with ten miles of sandy white beaches. Whether you are fishing, surfing, or simply soaking up the sun, plenty of options are at your disposal.

Over 20 companies offer inshore and offshore fishing expeditions. White and Blue Marlin love this bay, so grab your tackle box and reel one.

Adventurers will enjoy the opportunities to parasail, kayak, and surf at novice and professional skill levels.

Seacrets Distilling Company is the first distillery opened in Worcester County since the end of prohibition in 1933. Take a tour to learn about the entire process, from grain to bottling.

Chesapeake Ghost Walks are the ideal tour for those who appreciate a bit of spooky in their holiday. Stroll down the historic area to hear tales of maritime losses of years gone by. Learn about the architecture of the local structures, all while being regaled with stories about their original occupants.

Whether you are an adventure seeker, a seafood aficionado, a beachgoer, or a history buff, there is truly something for everyone in the Chesapeake Bay. Perfect for those wanting a bit of everything in their "chill." So unplug and take a step back in time to find out why locals refer to it as their "mother of the waters." With unlimited year-round attractions, the best time to visit is now.