8 Most Beautiful Small Towns on the Chesapeake Bay in 2024
The Chesapeake Bay is the largest estuary in the US and the third largest in the world. Over 18 million people and 3,600 wildlife species inhabit the region, which stretches from Havre de Grace, Maryland, to Norfolk, Virginia. Baltimore and Norfolk are notable cities in the region, but many beautiful coastal towns dot the landscape, each with its own story.
The bay has been a vital waterway for shipping, commercial fishing, and military defense, so an amalgamation of histories makes this part of the mid-Atlantic region unique. Boating and fishing are popular here, but quaint downtowns, beautiful architecture, and historical sites also weave the fabric of these small communities. These are the most beautiful small towns in Chesapeake Bay in 2024.
Annapolis, Maryland
The historic Naval town of Annapolis, Maryland, is the capital of Maryland and home to the famed US Naval Academy. It is also known for its 19th-century architecture and the 18th-century Maryland House. The Hammond-Harwood House, built in 1774, is an elegant museum celebrating architecture. The Anglo-Palladian style home was the final work of architect William Buckley, and today is a famous museum with exhibits and guided tours.
The US Naval Academy was first opened in 1845, and today, visitors are encouraged to walk the historic grounds. The chapel is particularly touching as the crypt of John Paul Jones, the father of the US Navy, is underneath. 2024 promises to be another great year to visit for the Naval Academy graduation, the Blue Angels in May, and the sailboat show in October.
Oxford, Maryland
Oxford is a classic port town and one of the oldest in Maryland. Though officially 20 years older, the town's founding is considered to be in 1683. Many historic buildings and a charming downtown area with a town clock exist. One of the grand historic pieces of architecture is the Robert Morris Inn. Built in 1710, this elegant inn is the longest-running full-service inn in America and is a great way to absorb the town's history.
Other points of interest include the Oxford Museum, which houses local artifacts and exhibits donated by the townspeople and is a popular destination for school groups. The Oxford-Bellevue Ferry service started in 1683 and is believed to be the longest-running ferry service in the US. Several events in 2024, like the Oxford Heritage Regattas, Cardboard Boat Races, and Christmas on the Creek, make this historic town even more fun to visit.
Cambridge, Maryland
Cambridge, Maryland, is a small town on the Choptank River. It was established in 1684 and is one of the oldest colonial towns in the United States. This coastal community has a historic downtown area, and High Street, referred to by some as the prettiest road in America, has homes from the 18th and 19th centuries.
Cambridge's famous maritime history can be relived at Ruark Boatworks, which preserves traditional boatbuilding skills, and the Richardson Maritime Museum. There is also a mural on Race Street honoring the blue-collar roots of this historic town. Cambridge is a fantastic town to visit, and 2024 promises several events, including the Ironman challenge in September. For those less inclined to compete, there is the Classic Powerboat Regatta on the Choptank River in May, with a pre-race concert on May 17th.
Havre de Grace, Maryland
Havre de Grace, Maryland, is a classic coastal town known for its bay views, cultural scene, and museums. It is a perfect town to explore on foot, and it has many parks and walking trails, such as Concord Point Park. The park is home to Concord Point Lighthouse and attractions like the Havre de Grace Boardwalk and Promenade.
The historic town has an active community, and plenty of events are being held this year. First Friday events occur monthly in Havre de Grace, with downtown streets closing for family-friendly vendors. This event is a great way to experience the town and the people that call it home. Other events include the monthly Poetry Slam and a live viewing of the Rocky Horror Picture Show.
Solomons, Maryland
Solomons, Maryland, is also known as Solomons Island and is notable as a prominent boating hub. It is at the mouth of the Patuxent River at the bottom of the Governor Thomas Johnson Bridge. The bridge, which is 135 feet high, provides an aerial view of the gorgeous town.
Several cultural attractions are here, such as the Calvert Marine Museum, the Annmarie Sculpture Gardens and Arts Center, and Calvert Cliffs. This year, several live events are being held, including live musical acts and the annual Solomons Dragonboat Festival. The Tiki Bar and Grill on Charles Street is a fun place to watch live acts, and there is a different band every week. The race is in August, and several rowing teams are scheduled to face off. The website is accepting registration applications for those wishing to compete.
Irvington, Virginia
Irvington, Virginia, is a charming town on the Rappahannock River. It is famous for its fresh blue crabs and oysters, quaint downtown, and friendly atmosphere. There are several nationally recognized bed and breakfasts like the Hope and Glory Inn and Vineyard. The luxurious inn has gorgeous rooms and cottages, many with garden views.
Another notable bed and breakfast is the Tides Inn, which hosts several seasonal events. The events are centered around the Live Like a Local program and include wine and cheese river cruises and walks along the Shoreline Trail. This itinerary is a fantastic way to fully experience this charming and rustic village.
Williamsburg, Virginia
Williamsburg is a historic town that served as Virginia's capitol from 1699 to 1780. The city played a significant part in the American Revolution and formed the "historic triangle, " including Jamestown and Yorktown. It is known worldwide as the largest center for American Colonialism preservation and the living history of Colonial Williamsburg.
Colonial Williamsburg is filled with educational opportunities, museums, and architecture from the 17th and 18th centuries. This year's events include Hands-On Crack The Code, where visitors can solve authentic Revolutionary War problems through coded messages hidden around the colony, and Street Theater: A Way Forward. Williamsburg is one of the most historical towns in the US, and you will find entertaining and educational activities throughout the year.
Cape Charles, Virginia
Cape Charles, Virginia, is a small coastal community with deep historical significance. It is famous for its commercial fishing fleet and fresh oysters, crabs, and clams. Established in 1884 for the railroad industry, it is one of the earliest planned communities, and several vintage train sites and exhibits still exist today.
The walkable Cape Charles Historic District has been on the National Register of Historic Places since 1991 and includes remnants of the town's railway and fishing history. Several annual events are held there, including free weekly concerts in Cape Charles Central Park. Many events are also held in the vibrant downtown area, including two crab fests in August and September.
Why Visit Chesapeake Bay's Small Towns in 2024?
The Chesapeake is one of the most storied regions in America. It includes historical towns like Williamsburg, Virginia, and Annapolis, Maryland, as well as coastal towns with rich maritime histories, such as Cape Charles, Virginia. This region always has something to do, like historical walking tours, boating, and shopping in the downtown districts. These beautiful towns are hosting many events this year, which makes them even more exciting to visit in 2024.
