10 Prettiest Towns In Chesapeake Bay
Do the smell of salt water, an ocean breeze, and cobblestone streets sound like the perfect combination for your next getaway? From the artistic hub of Easton, Maryland, to "The City of Anne," Urbanna, Virginia, there are many beautiful towns in the Chesapeake Bay area waiting to explore. These top ten prettiest towns in Chesapeake Bay will have you soaking up the sun and enjoying that easy East Coast slow living all at once.
Easton, Maryland
Tucked away on the Tred Avon River, this adorable small town is home to just over 17,000 inhabitants and was once named the 8th Best Small Town in America. Situated not far from bustling cities like Baltimore, Washington, and Annapolis, Easton has become a unique hub known best for its vibrant arts and culinary community located in a stunning historic downtown. You don't want to miss Easton on your next ride around the Bay.
Chesapeake City, Maryland
This hidden gem is home to less than 800 people year 'round and one of the most beautiful spots Maryland has to offer. Situated on the Black Creek, on the biggest estuary in the world, this stunning spot is perfect for fishing, shopping, and sightseeing on your next getaway from the city. Try out the famous fresh oysters, or jump on the winery trail and sip some of the finest wine the Atlantic Coast has to offer.
Oxford, Maryland
You can't go wrong visiting one of the oldest towns in Maryland, Oxford has been awaiting your arrival since 1666. Sitting right on the water's edge in Chesapeake Bay, this stunning colonial town is home to Victorian homes and a buzzing art scene. Fill up on some of the freshest seafood on the Atlantic Coast and relax in a quaint 19th-century home at the Oxford Inn.
Chestertown, Maryland
About 90 miles from Baltimore, this pretty town sits on the water's edge and is home to just 5,600 inhabitants. Hugging the Chester River, this stunning town holds some of the country's most well-preserved 18th-century homes, second only to Annapolis. With its beautiful historic downtown, lined with red brick streets and sidewalks, you will truly feel like you've stepped back in time on your next visit to Chestertown, Maryland.
Cambridge, Maryland
Sitting on the Eastern shore of Chesapeake Bay lays the prettiest town. Cambridge is the fourth most populous city in Maryland's Eastern Shore region and home to 13,000 people. It is well known for its quaint downtown, beautiful buildings, one-of-a-kind shops, and vibrant arts and culinary scene. Aside from some of the best seafood Maryland has to offer, visitors come to Cambridge on a hunt for its well-known haunted Victorian homes. If you like a good ghost story, Cambridge might just be for you.
Saint Michaels, Maryland
One and a half hours outside of Washington DC, Saint Michaels was the home of tobacco growers and shipbuilders dating back to 1677. Now home to just over 1,000 inhabitants, this quaint waterside town sits on Eastern Bay. Proudly nicknamed "the town that fooled the British" from the War of 1812, Saint Michaels is equally popular for being the home of Maryland Crabs. Visit Saint Michaels and taste some of the best food on the Atlantic Coast in peak crab season, April through November.
Onancock, Virginia
North of Virginia Beach, on the Eastern shore of Chesapeake Bay, lays the quaint town of Onancock, Virginia. Home to The North Street Playhouse, a well-loved and popular theater founded in 1986, bringing theater lovers from across the country to its productions annually. If you plan to visit the popular Tangier Island, you will also want to catch the ferry from the historic downtown in Onancock, running seasonally from late May through early October.
Cape Charles, Virginia
Less than an hour North of the Virginia beach shore, you will find the beautiful town of Cape Charles, Virginia. Spend your day hiking through the breathtaking Cape Charles Nature Reserve or walk the boardwalks on the National Registry of Historic Places at its water's edge. Full of art galleries, shops, and restaurants, as you walk along this stunning shore town, you may even find yourself at the world's most Instagrammable bookstore, Peach Street Books.
Irvington, Virginia
Inside the Western shore of Chesapeake Bay, sitting on the Rappahannock River is the picturesque town of Irvington, Virginia. Just over an hour from Richmond, you will find yourself sitting seaside in one of the prettiest towns on the Atlantic Coast. This designated historic district, on the Northern Neck peninsula is home to just under 500 permanent residents. Nautical enthusiasts come to Irvington to explore the well-known Steamboat Museum that highlights the history of Steamboats in the Chesapeake Bay. Rest and relax at the famous The Tides Inn which has been welcoming guests since opening its doors in 1947.
Urbanna, Virginia
Urbanna, meaning "City of Anne," was named in honor of Queen Anne, and holds a population of less than 500 inhabitants who are lucky enough to call it home. From beautiful docks on the water's edge to the historical downtown lined with beautiful buildings, shops, and restaurants, Urbanna has something for everyone. More importantly, since 1958, it has been the host of the Urbanna Oyster Festival, taking place the first weekend of November, bringing in over 75,000 visitors to this quaint town.
Next time you are looking to leave the city and get a taste of all the beauty Chesapeake Bay has to offer, add these top prettiest towns to your list. You won't be disappointed when you have the opportunity to experience all of the stunning scenery, history, and culture, and don't forget those Maryland Crabs. Chesapeake Bay is a sight to be seen, so jump in the car and head to its salty shores today.
