The Most Picturesque Small Towns in Chesapeake Bay
Chesapeake Bay is the United States’ largest estuary, stretching from the Susquehanna River to Hampton Roads and bordering Maryland and Virginia. While still a vital commercial and industrial waterway, efforts to clean up and preserve the bay have increased its status as a tourist destination. Chesapeake Bay offers visitors great water recreation, fishing, and nature sightseeing, and also numerous waterfront towns that are overflowing with history and charm. Choosing only six picturesque bayfront towns is a tall task, so let this be your guide as a starting point for your next visit to the Chesapeake Bay.
Stevensville, Maryland
Kent Island is the biggest island in the Chesapeake Bay, covering about 31 square miles, and Stevensville is the largest town on said Island. Stevensville used to be the main depot for the cross-island railroad that served the ferries crossing the bay prior to the arrival of the Chesapeake Bridge that connects Kent Island to Annapolis and Maryland’s Eastern Shore. Summertime tourists venture onto Kent Island to explore attractions like Terrapin Point Public Beach, Ferry Point Nature Park, Kent Narrows, and Stevensville, which still maintains its historic railroad-town character. Despite being in the middle of the bustling Chesapeake Bay, Stevensville offers a picturesque reprieve from big-city life.
Urbanna, Virginia
For much of the year, Urbanna is a sleepy town of about 500 with a beautiful waterfront that first docked tobacco boats in 1680 and now welcomes pleasure boats. Things pick up in Urbanna during the summer, when tourists come by boat or car to take in the sights and enjoy some fresh Chesapeake oysters at Walton’s or Shores & Ruark. But Urbanna’s real time to shine comes in November when up to 75,000 people flock to the town to experience the Urbanna Oyster Festival. Whether you prefer to visit when the town is calm and quiet or prefer to see it bursting with energy, Urbanna always shines in its picturesque setting.
Oxford, Maryland
Like Urbanna, Oxford is a small waterfront town with a nearly 350-year history as a Chesapeake port. While plenty of pleasure boats line the docks, especially on sunny summer days, Oxford still supports a small fleet of fishing boats that bring in the day's catch. Not surprisingly, downtown Oxford is home to several excellent seafood restaurants, along with shops, boutiques, and historic structures like the restored colonial-era Customs House. A day trip or weekend excursion to Oxford also offers a great bonus—take the Oxford-Bellevue Ferry (established in 1683) across the Tred Avon River to explore the equally picturesque town of Bellevue.
Williamsburg, Virginia
Williamsburg is a worldwide tourist destination because of Colonial Williamsburg, a 300-acre living history museum that recreates 1700s life via restored and rebuilt buildings and knowledgeable, costumed re-enactors. Walking through Colonial Williamsburg is free (a fee applies to enter the buildings), and you can continue your walk onto the historic campus of the College of William and Mary, founded in 1693. From there, complete your walking tour in Merchants’ Square, a shopping and entertainment district with more than 40 shops, including both national retailers and local staples like Wythe Candies.
Annapolis, Maryland
Annapolis has roughly 40,000 residents and has been Maryland’s state capital since 1694, but its compact downtown provides a small-town feel. Start your walking tour at the 1779 Maryland State House, which is still in use, then work your way slightly downhill through downtown Annapolis’ narrow streets. Surrounded by colonial-era brick buildings as you go, take time to stop at local hotspots like Chick & Ruth’s Delly and the Lucky Knot boutique before reaching the stunning waterfront. Also, be sure to venture over to the United States Naval Academy, which has called Annapolis home since 1850.
Saint Mary’s City, Maryland
Saint Mary’s City, which is actually a little town with only about 1,000 residents, was founded in 1634 as the first English settlement in the colony of Maryland. Similar to Williamsburg (but on a smaller scale), downtown Saint Mary’s City’s historic core has been restored into a living history area with costumed interpreters, restored buildings, and four museums. More history awaits along the beautiful waterfront, home to an impressive recreation of the 1634 sailing ship Maryland Dove. After taking in your fill of history, relax and recharge by venturing along Saint Mary’s City’s numerous nature trails.
Many of the towns that line the shores of Chesapeake Bay have been around for more than 300 years, surviving centuries of changes and challenges. Nowadays, these former fishing villages, tobacco ports, and railroad hubs draw on their historic charm and the bay's unsurpassed natural beauty to attract tourists. While big cities like Baltimore, Washington, and Norfolk are always close by, no trip to the Chesapeake Bay is complete without a tour of some of its beautiful small towns!
