Chesapeake Bay
The Chesapeake Bay is arguably our region’s greatest natural asset and favorite playground. The shoreline and tributaries of the Bay measure 11,864 miles of scenic beauty, encompassing a huge section of Virginia and Maryland’s eastern coastline. To compare this incredible fact, consider that the Chesapeake coastline is longer than the entire west coast of the United States.
Lovingly referred to as the Eastern Shore, the Bay is dotted with quaint villages and a few medium-size cities. Many of these population centers were founded and developed as seafaring economies in pre-Colonial times. During the summer months, Bay towns swell with visitors in seek of cool breezes and abundant water activities, and they are sanctuaries for recreation enthusiasts who enjoy boating, fishing, kayaking, crabbing, waterskiing, paddle boarding, sailing and jet skiing.
Spending time in or beside the Bay conjures an entirely different feeling from our busy day-to-day lives. Beach combers, nature lovers, lighthouse devotees and history buffs all find enticements here. Some come to windsurf from the sandy beaches of Sandy Point State Park or commune with seabirds at Blackwater National Wildlife Refuge. Many go boating around the coves of Terrapin Nature Park on Kent Island or ride the ferry to explore historic Smith Island. Others make a pilgrimage to survey the path Harriett Tubman took, leading enslaved people to freedom on the Underground Railroad. The Harriett Tubman Byway winds through 125 miles of Dorchester and Caroline County, including the banks of the Choptank River. You can take a scenic paddlewheel ride with Choptank Riverboat Company, or hop a sightseeing pontoon on River Run Cruises departing from Mathew’s Landing. The Bay also serves as a thoroughfare for cruise ships leaving from the Port of Baltimore.
The word Chesapeake comes from the Algonquin Indian name for “great shellfish,” which explains why the Bay is also ground zero for the best Mid-Atlantic seafood, especially the iconic blue crab. Standout towns worth investigating include Annapolis, St. Michaels, Chestertown, Oxford, Cape Charles, Cambridge, Havre De Grace, Solomon’s Island and Chesapeake Beach. Distance varies depending on destination, but Annapolis is one hour, and St. Michaels is 2.5 hours.
Assateague Island
Assateague Island is a remote atoll north of Chincoteague Island. This protected landscape is best known for the wild ponies that have survived in Assateague for centuries. Part of the Delmarva Peninsula, the protected barrier island on the edge of the continent feels very different from the nearby beach communities.
Maryland and Virginia each claim a portion of Assateague Island. The landmass has been overseen and preserved by the National Park Service since 1965. The Virginia portion is accessed through Chincoteague Island and is home to The Chincoteague National Wildlife Refuge, which was established in 1943.
Assateague has 37 blissful miles of coastline with picturesque sandy beaches on the Atlantic Ocean. Diverse habitats thrive inland, including woodlands, marshlands and dunes. NPS Rangers offer programs in the warmer months on the unique environment and history of Assateague Island.
Watermen from the region “farm” the waters around Assateague Island in search of clams and oysters. Many visitors come to this National Seashore to watch the ponies, swim, surf, camp, bird watch, kayak and sunbathe. Kayak landing areas in Maryland are located across the bridge from the Assateague Visitor Center and by the Ocean City Inlet.
The southern third of Chincoteague National Wildlife Refuge is located on Assateague Island, and every July the world-famous Pony Swim takes place, where the wild horses are rounded up and the foals sold at auction. This process helps to keep herd numbers manageable and raise funds for the Chincoteague Volunteer Fire Company, the organization that owns the Virginia ponies. Another attraction in this area is Wallops Island, a NASA flight facility just south of Chincoteague. Drive time is about three hours.
Yorktown
The charming colonial-era hamlet of Yorktown was the location for a pivotal battle in the Revolutionary War. On Oct. 19, 1781, General Charles Cornwallis surrendered to General George Washington in Yorktown. Prior to this long-awaited resolution, the community was under siege, and the final battle between the British and the American forces raged on both land and sea. The story comes alive with a visit to Yorktown National Battlefield.
Today, the charming and well-preserved town on the York River has miles of shoreline and minimal development. Located beside the Yorktown Riverfront is the new American Revolution Museum at Yorktown, a living history complex with colonial-era settlements and a modern museum that tells the story of early American history from multiple voices, including women, children, Native Americans, the enslaved population and even pets.
Part of Virginia’s Historic Triangle, Yorktown’s Riverwalk Landing has shops, restaurants and a park, where you can enjoy views of the river. Along with the town’s fascinating history, water activities abound. Visitors can board the tall ships from Yorktown Sailing Charter’s fleet of sightseeing cruises; the schooners are replicas of ships piloted during the Revolutionary War. It’s a great way to see local wildlife, including dolphins and osprey.
Kids love Yorktown’s pirate adventure cruise, where costumed characters tell stories and fire off a cannon. Williamsburg Charter Sails offers hands-on instruction in sailing a 32-foot Hunter Sloop, and swimmers splash around at Yorktown Beach, with its fishing pier and shower facilities. For more water fun, check out nearby Waller Mill Park, Little Creek Reservoir Park and Chickahominy Riverfront Park, where you can rent canoes, kayaks and paddleboats. Drive time is 2.5 hours.
Jamestown
The Jamestown area of Greater Williamsburg, part of Virginia’s Historic Triangle, offers lots of things to do, both on and off the water. Start your visit at Historic Jamestown, where the first settlers arrived in 1607 and founded the community of Jamestown, named after King James of England. Today, the area is set aside as a national park, and there’s a beautiful coastal hike along the James River.
The next stop is Jamestown Settlement, a modern museum where visitors can learn about the lifestyle and trials of the first English settlers in America. The museum features high-tech, interactive exhibits, including one honoring Pocahontas, the Powhatan Indian woman who befriended the English settlers. The outdoor section, located on the banks of the James River, is a recreation of a Powhatan Indian Village and replica of the James Fort. Here, visitors can learn about pre-colonial life from living history actors. Also at Jamestown Settlement, museum guests can board replicas of three 17th century vessels, the Susan Constant, Godspeed and Discovery—sailing ships that originally transported early English settlers to Jamestown.
Directly across the road from Jamestown Settlement is Jamestown Beach Event Park, where you can rent kayaks, go fishing and have a picnic. At the nearby James City County Marina, you can rent kayaks, canoes, paddleboards and bikes, as well as take a sightseeing pontoon ride down the James River. Don’t miss the Billsburg Brewery overlooking the marina. Jamestown is 12 miles from both Water Country USA and Great Wolf Lodge. Drive time is 2.5 hours.
Delmarva
Delmarva is named for the peninsula that runs from southern Delaware, down the Maryland coastline and then south along Virginia’s Eastern Shore. Each of the towns bordering the Atlantic Ocean has its own appeal and vibe. At the top of the peninsula are the Delaware towns of Lewes, Rehoboth Beach, Dewey Beach and Bethany Beach.
Rehoboth and Bethany are especially family friendly with festive boardwalks, while Dewey is known for its live music and party atmosphere. Historic charm and Cape Henlopen State Park have made Lewes a top destination. All are bounded on the east by the Atlantic Ocean and the west by Rehoboth and Indian River Bays. There are countless opportunities for seaside entertainment in these communities including kayaking, canoeing, jet skiing, windsurfing, paddle boarding, sailing and fishing.
Further south are the Maryland coastal towns of Fenwick Island and Ocean City. Ocean City is particularly popular, thanks to its 2.5-mile boardwalk, high rise condos, buzzy nightlife and world-class deep-sea fishing trips. Ocean City’s famous amusement park, Trimpers Rides, located at the southern tip of the boardwalk, is more than a century old and offers endless entertainment.
Moving into Virginia are the pastoral shores of Chincoteague and Assateague Island National Seashore. This mostly undeveloped section of the peninsula is populated by hamlets like Wachapreague, Exmore and Cape Charles. At the south end, the 23-mile Chesapeake Bay Bridge-Tunnel crosses into Virginia’s Tidewater region and Virginia Beach.
There are countless water activities in Delmarva, as these communities were established to take full advantage of the rolling waves and endless beauty of the Atlantic Ocean. Along with surfing, boating, fishing and swimming, there are action-packed water parks like Jungle Jim’s in Rehoboth Beach, Thunder Lagoon in Fenwick Island and Jolly Roger Splash Mountain in Ocean City, to name a few. Drive time to Ocean City is about three hours.
Virginia Beach
Virginia Beach is made up of seven distinct districts, each with their own attractions and personality. The urban section—the city of Virginia Beach—offers a variety of cultural activities like museums, shopping and restaurants—with many places where vacationers can spend a day, including the Virginia Aquarium and Ocean Breeze Waterpark.
The hub of entertainment is Virginia Beach’s Oceanfront, with its 40-block boardwalk, modern hotels and waterfront dining options. The Neptune Statue is Virginia Beach’s iconic symbol, and this Roman god extends a hearty welcome to those seeking a classic beach vacation of sunbathing, swimming, surfing, cycling the boardwalk, as well as frolicking at Atlantic Fun Park. At nearby Rudee Inlet, take a ride on the Rudee Rocket speed boat or try flyboarding, a water-powered jet-propelled flight machine over water.
The coastal community of Sandbridge is for those seeking secluded beaches and luxury home rentals. The natural landscape is perfect for long walks, fishing, shell seeking and bird watching. You can rent pontoon boats, jet skis and take guided kayak tours in the Sandbridge area. Keep your eye out for dolphins.
First Landing State Park is the heart of Virginia Beach’s recreational activities like hiking and biking. This national landmark is also Virginia’s most visited state park thanks to the 1.25 miles of serene marshes, tide pools, sand dunes and the historic Cape Henry Lighthouse. The name First Landing refers to the English settlers who landed here in 1607.
Virginia Beach is adjacent to major cities, including Norfolk, Hampton and Newport News—all at the confluence of the Chesapeake Bay and Atlantic Ocean. Virginia Beach is just north of the pristine Back Bay National Wildlife Refuge. Drive time from Fairfax is 3.5 hours.
Northern Neck
The rural landscape between Fredericksburg and the Chesapeake Bay is known as the Northern Neck of Virginia. The peninsula is 90 miles long with more than 1,200-miles of mostly undeveloped shoreline between the Potomac and Rappahannock Rivers. The region is the birthplace of three of the first five American presidents—George Washington, James Madison and James Monroe.
The tranquil forests and brackish water of the Northern Neck make it a haven for sea life. Watermen have farmed here for generations, and the region is famous for the cultivation of oysters. You can take a cruise with a number of boat companies like the Tangier Rappahannock Cruise from Reedville to Tangier Island, a lovely day trip to the quaint island village located in the Chesapeake Bay. The Tides Inn Resort offers daily tours of the Rappahannock River, especially their delightful sunset cruise. Virginia Watermen’s Heritage Tours demonstrate to passengers the history and culture of Virginia’s watermen, including a chance to go oyster dredging, crabbing and birdwatching. No time for a cruise? You can learn more Northern Neck history at the Reedville Fishermen’s Museum.
Belle Isle State Park encompasses 7 miles of shoreline in the Northern Neck’s Rappahannock River. Visitors can explore the tidal wetlands on a guided canoe trip, paddle boards or rented kayak. It would be hard to find a more peaceful place to survey wildlife and shorebirds.
The village of Colonial Beach is a seafaring community with a small boardwalk and marinas that offer fishing charters and rent kayaks. At the end of the day, relax at Dockside Restaurant and Tiki bar to behold the sunset. Drive time is three hours (to Reedville).