These Towns in the Chesapeake Bay Come Alive in Winter
Winter is commonly associated with snow, and while you may not find more than 5 inches annually of that in the Chesapeake Bay, the season still is noteworthy with chilly evenings coupled with nippy air. Towns along the Chesapeake Bay appeal to visitors during the colder months as the off-season permits more time and a slow pace to discover all that the destination boasts, from museums to wildlife refuges and themed events.
With festivals for Thanksgiving, Christmas, and New Year, during winter these towns are covered with holiday lights. Be it Annapolis or Cape Charles, look to the calendar for seasonal activities like ice skating, home tours, and band parades.
Cape Charles, Virginia
Cape Charles, nestled at the tip of Virginia's Eastern Shore, is not just about pristine beaches and charming Victorian architecture. Throughout December, the town twinkles with festive lights on its lampposts as horse-drawn carriage rides jingle down Mason Avenue, the main street, to Strawberry Street. Meanwhile, the Cape Charles Museum provides an insightful journey into the town's seafaring past, featuring artifacts from the heyday of the railroad and steamship era.
Kiptopeke State Park, just minutes away, is where you can hike or bike along the 5.1 miles of scenic trails or kayak through the calm waters of the Chesapeake Bay. You can also head to the Cape Charles Candy Company, a cozy spot to bring your kids to enjoy chocolate fudge.
Rock Hall, Maryland
Winter in Rock Hall, Maryland, invites birdwatchers to the 2,286-acre stretch of Eastern Neck National Wildlife Refuge, a seasonal sanctuary for migratory waterfowl, most prominently tundra swans. Simultaneously, the over 9 miles of hiking trails unveil the town's rich ecological diversity, including marshlands and woodlands.
While a stroll along the Rock Hall Harbor lets you admire picturesque boats bobbing in the chilly waters, you should not miss the incredibly clear sunset view from Ferry Park. Winter activities on the harbor also include crabbing and oyster shucking, highlighting the town's maritime traditions. Adventurous spirits can embark on a winter kayaking expedition, gliding through the quiet inlets with Chester River Kayak Adventures.
Williamsburg, Virginia
You will know winters have arrived in Williamsburg when you see 18th-century life with costumed interpreters showcasing winter festivities of yesteryear in the Colonial Williamsburg Historic Area. You will witness craftsmen ply their trade, from blacksmithing to candle making, offering an authentic glimpse into America's revolutionary past in addition to the option of taking carriage rides around the place.
A trip to the Busch Gardens Christmas Town is a must for an enchanting seasonal event decorated with millions of lights, festive shows like Christmas Town Express, and exhilarating roller coaster rides. Whether you are an expert or a novice, it is also the season to put on ice skates and enjoy the art of ice skating at Liberty Ice Pavilion.
Annapolis, Maryland
The United States Naval Academy, a historic institution in Annapolis since 1845, welcomes visitors to explore its grounds. Winter is an ideal time to witness the Silent Drill Platoon refining their skills with precision and discipline.
The winter season also hosts the Midnight Madness series, where local shops extend their hours, making it an ideal time for unique, handcrafted holiday finds amid holiday lights. Winter enthusiasts can also spend an afternoon at Quiet Waters Park, where the ice skating rink steals the spotlight. Ice skating classes also take place alongside skilled skaters showing off their moves.
Easton, Maryland
Easton captures attention with Federal-style architecture prevalent in its historic district. You can pop into the Talbot Historical Society for its beautifully maintained Federal gardens or take note of the exhibitions in the 1783 Mary Jenkins House from the Georgian-style era. The Waterfowl Festival, a winter highlight, celebrates the area's rich birdlife through events like Chesapeake Mermaid performances, a sportsman's expo, and a wildlife art show.
The Pickering Creek Audubon Center is the town's nature spot, encompassing 450 acres of marshes, meadows, wetlands, mature hardwood forest, and cropland. The Center holds activities including climate watch bird survey, tracking animals in winter, nature walks with the director, and many more during the colder months. You can also stop by the Avalon Theatre for winter performances ranging from classical concerts to contemporary plays.
Cambridge, Maryland
Cambridge is the place for winter travelers to tour the Richardson Maritime Museum, housed in a former oyster-packing facility, giving insights into the town's seafaring past using historic boat replicas, artifacts, and boatbuilders' tools. Winter is an ideal time to appreciate the museum's exhibits without the summer crowds.
Moving on, the nearby Blackwater National Wildlife Refuge calls visitors to watch bald eagles and snow geese gracing the wetlands during the colder months. For more than seven decades, the historic High Street has been the route during the Cambridge Dorchester Christmas Parade, allowing people to dress up and sway with band performances under twinkling lights.
Onancock, Virginia
Onacock's winter charm is heightened during the Onancock Christmas Homes Tour, where six restored historic homes in the town adorned with festive decorations open their doors to visitors looking at classic architecture. Furthermore, the 1790s Ker Place Museum, a Georgian-style home turned museum, is famous for orchestrating events, including Lights on the Lawn, where you can drive around the town and enjoy the lawns with trees elegantly draped with festive embellishments and lighting. You may also purchase tickets for live theatrical productions at North Street Playhouse, which has nearly 15 events every season.
Saint Michaels, Maryland
The focal point of Saint Michaels is the Chesapeake Bay Maritime Museum. Here, you can climb the Hooper Strait Lighthouse, witness the restoration of historic boats, or sift through 80,000+ historical objects.
The winter ambiance is in full swing with the town's Annual Christmas in St. Michaels event, transforming the streets into a festive wonderland with holiday-themed activities such as a lighted boat parade, marketplace and sweet shoppe, Talbot Street parade, and Breakfast with Santa. Lastly, the 18 types of wine taste even better in the chilly evenings at St. Michaels Winery.
The winter charm of towns nestled along the Chesapeake Bay is nothing short of enchanting. From the cozy streets of Annapolis adorned with twinkling lights to the serene waterfronts of St. Michaels, the crisp winter air celebrates the spirit of the season, whether it be dazzling light displays, lively parades, or outdoor ice skating rinks. While nature lovers can keep an eye on migratory birds, history buffs can delve into the rich heritage of each town through museums and guided tours.
