Nowhere else in the world can you enjoy the same blend of delights that make the Chesapeake Bay unique. It’s surrounded by places as placid as the marshes of Blackwater National Wildlife Refuge and as upbeat as Fell’s Point’s Broadway on a Saturday night.
If you did it right, it would take you a lifetime to make your way down one shore of the Bay and up the other while you savor the distinct character of each waterman’s village and every inspirational water view, whether you’re traveling on the water or on one of its many scenic byways.
Along that journey, you’ll come across the people who populate these places: the oystermen who still dredge the bottom from the deck of a hundred-year-old skipjack, the boatwrights who recreate traditional wooden vessels from raw timber in St. Michaels, the riverkeepers who plant oyster spat to help restore the waterways, and the artists who capture all of the Bay’s rich natural history and cultural heritage in water paint or song.
You’ll gain a sense of the rhythm of the seasons on the Bay—the piercing whistles of the first ospreys returning in the spring from their sojourn in Central America, the melifluous trill of the red-winged blackbird snatching summer bugs in the reeds, the symphonic calls of Canada geese gathering by the thousands along an autumn marsh, the lone cry of a bald eagle circling above a frozen tidal pond.
The range of outdoor experiences can be breathtaking. An enterprising adventurer could combine cycling, sailing, hiking, bird watching, swimming, and paddling all in one weekend trip. On the other hand, you might prefer lounging in the cockpit of a sailboat anchored in a remote cove or watching a moonrise from an Adirondack chair perched on the end of a pier.
The palate of food and drink is no less expansively encompassing; witness the distinct “terroir” of the wines from diverse vineyards or the “bay-oir” of oysters from various rivers. Restaurants range from dockside dining on picnic tables covered with rolls of butcher paper to elegant, candlelit settings. Menus feature not just the best seafood in the country—Maryland blue crabs and rockfish, to name just a couple of favorites—but also recipes for traditional fried chicken, stuffed ham, and barbecue passed down from generation to generation.
You can spend the night in a historic inn once owned by one of our Founding Fathers, a cozy B&B at the tip of a remote island, or a five-star luxury hotel in one of the Bay’s premier waterfront destinations. Of course, there’s always the option of cruises aboard boats under sail or power, with overnight stays either anchored out or docked at a modern marina with all the amenities of a posh country club.
Capt. John Smith had it right in 1612 when he wrote ecstatically to the folks back in Merrie Olde England, describing the Chesapeake Bay as “the land of pleasant living.” It still is, as you’ll see when you explore some of the highlights selected by our readers and contributors.
Most Charming Chesapeake Town: St. Michaels, Md. (tie)
This quintessentially quaint village on the Eastern Shore checks off on all categories that make for the ideal Chesapeake destination, whether visiting by boat or car: a world-class museum, waterfront restaurants, cocktail cruises, and a strollable main street festooned with art galleries and antique shops, luxury hotels and charming historic inns. Best yet, you can hang out with the locals at the Carpenter Street Saloon. tourtalbot.org
Most Charming Chesapeake Town: Mathews & Yorktown, Va. (tie)
Contrasting towns tie for top honors on either side of the York River: Mathews, with its rural charm, art galleries, seafood and barbecue, birding and wildlife, and proximity to historic New Point Comfort Lighthouse; and Yorktown, with its 18th-century brick buildings, where a stroll along Riverwalk Landing takes you by riverfront restaurants, boutiques, and the Watermen’s Museum. The American Revolution Museum interprets the nearby Yorktown Battlefield National Park. visitmathews.com; visityorktown.org
Best Public Beach: Sandy Point State Park and Flag Ponds Nature Park, Md. (tie)
The beach at Sandy Point stretches more than a mile. Off to the right, the twin spans of the Chesapeake Bay Bridge swing across to the Eastern Shore, while the silhouette of the Sandy Point lighthouse marks the horizon on your left. Sharp-eyed beachcombers at Flag Ponds near Lusby, Md., can find shark’s teeth and other fossils from the Miocene era.
Best Public Beach: Yorktown Beach, Va. (tie.)
Historic Yorktown boasts a two-acre beachfront where locals and visitors alike enjoy boating, swimming and fishing. A specially-adapted submersible wheelchair is available for rent, allowing beach access to everyone. There’s an ADA-accessible fishing pier and grassy area for picnics, plus kayaks, paddleboards, and bikes for rent. You can also book a ticket on the Schooner Alliance for a sail on the
York River. visityorktown.org
Best Couples’ Escape: Wylder Hotel; Tilghman Island, Md.
This boutique hotel welcomes both couples and their canine companions on its 9.5-acre waterfront site, home to 54 rooms and suites in the main hotel or the adjacent cottages. But note, while dogs can lounge on the porch with you or ride along on your rented kayak or SUP, they aren’t allowed in the heated saltwater pool. The chefs at Tickler’s Crab Shack and Bar Mumbo base their menus on all that’s fresh from the onsite garden and watermen who bring seafood daily to Tilghman Island’s docks. wylderhotels.com
Best Couples’ Escape: The Hornsby House Inn, Yorktown, Va.
A perennial favorite among loyal CBM readers, this homey B&B set on Main Street in historic Yorktown features five spacious guest rooms, each with its own private bath. It’s an easy stroll to restaurants and shops, and the inn is convenient to Yorktown Battlefield, Colonial Williamsburg, and other historic attractions.hornsbyhouseinn.com
Best Family Getaway: Annapolis, Md.
Begin your journey through the past 400 years at the new History of Annapolis Museum at the foot of Main Street. All of the attractions are an easy stroll or a fun water-taxi ride away, including the United States Naval Academy, Annapolis Maritime Museum, and homes of the Maryland signers of the Declaration of Independence. Restaurants, gift shops, and art galleries line the streets from State Circle to City Dock. visitannapolis.org
Best Family Getaway: Bethany Beach, Del.
This family-friendly town on the Atlantic coast of Delaware is known for sun and surf as well as for the all the local restaurants and tax-free shops along the broad avenue leading down to the boardwalk and the beach. Charming hotels and B&Bs offer accommodations, though many private homes are also available for weeklong rentals. The town abuts the Delaware Seashore State Park, with its miles of secluded beaches on one side and the dunes and surfing area of Fenwick Island State Park on the other. visitdelaware.com
Best Historic Site: Historic St. Mary’s City, Md., and Harriet Tubman Underground Railroad National Historic Park, Church Creek, Md.
These tied winners each provide a unique perspective on Maryland’s diverse history. The colony’s first settlers arrived at St. Mary’s City aboard the Ark and the Dove in 1634. An authentic reproduction of the Dove has just been launched and will soon be part of the town that serves as a museum of living history and archaeology interpreting Maryland’s original capital.
There are a number of ways to discover the heroic story of Harriet Tubman and the Underground Railroad, but the best is to follow in her footsteps. In Dorchester County, you can visit the authentic places where this great American freedom fighter was born, where she grew up, where she was forced to work, where she escaped from slavery to freedom, and most astonishingly where—at the risk of her life—she returned time and again to usher scores of family members, friends, and other enslaved people along a network to freedom known as the Underground Railroad. The museum, run by the National Park Service, is a great place to start, then take to the byways with a guide to sites along 125 miles of rural back roads and state highways.hsmcdigshistory.org, nps.gov/hatu
Best Bird watching: Blackwater National Wildlife Refuge, Dorchester County, Md.
Situated south of Cambridge along the Atlantic Flyway, this waterfowl sanctuary comprises more than 20,000 acres of marshland, forest and open water. It’s crisscrossed with five miles of hiking trails and 17 miles of water trails for kayakers and canoeists, or you can spot the diving ducks, geese, swans and other migratory birds from your car along a 3.6-mile wildlife drive. Odds are good that you’ll see some of the many American bald eagles that take refuge there. fws.gov/refuge/blackwater
Best Bicycling Excursion: Kent Island Cross-Island Bike Path, Md.
This seven-mile trail goes from Terrapin Nature Park on the shores of the Chesapeake Bay to the Kent Narrows Waterfront district. The trail affords pedestrians, runners and cyclists a unique opportunity to view wildlife in an environmentally sensitive setting while enjoying the scenery of the waterfront, canopied woodland and access to public parks. The trail is paved and ADA accessible, but it can be crowded during peak usage, so this may not be the ride for you if your goal is speed. kentnarrowsmd.com
Best Bicycling Excursion: Yorktown Battlefield Tour, Va.
Begin at the Visitor Center with a 16-minute introductory film of the story of the Siege at Yorktown, then explore the battlefield by bike on either of two self-guided tour routes that total 16 miles. Maps of the driving tours are available at the Visitor Center, and you can also download a smart phone app. Along the way, stop off at any of the park’s historic buildings, like the 1730 Nelson House that still bears scars from the 1781 battle. nps.gov/york
BEST OF THE BAY PICKS
Best Place to Remember that Fell’s Point was Once a True Seamen’s Village: Recreation pier, Baltimore
The lights (some 410 of them) spell “City Pier Broadway,” easily seen across the channel from Baltimore’s other great light show, the Domino Sugars sign. The white bulbs are screwed into the back of the “Rec Pier,” built in the 1700 block of Thames Street in 1914 to give the children of the working class a place to play without getting run over by a train or trampled by a team of horses.
It is now home to a luxury hotel, with rooms that cost more per night that than my father and his tugboat buddies made each month when tugs docked on either side of the pier. But when I stare up at the Great Seal of Maryland carved atop the building’s arch, I remember the old salts who once made this, the foot of Broadway the most interesting neighborhood in Baltimore: folks like Mister Olie, the whisky-drinking Norwegian engineer rattled all his life after his ship was torpedoed; Gilbert Lukowski, the tough-as-an-oyster-shell union boss representing longshoremen; Agnes Karcz Garayoa, with a heart as big as an Esskay ham who would throw you out on your butt at her mother’s saloon if you started trouble. And my father, “the Chief,” who parked his canary-yellow 1966 Mustang inside the building before going aboard the tug America to start the big-ass diesel engines that nudged great ships into port.
– Rafael Alvarez
Best Beach to Find Sea Glass: Hoopers Island, Md.
A few years ago, author Ellie Mercier presented me with a copy of her book The Sea Glass Companion. I learned that the bags of bright blue, green and white glass I’d seen in craft stores were not the real thing. One day, another friend who is a casual collector invited me to ride along with her to Hoopers Island. We walked the small beach where I found my first pieces of a brown bottle, a shard of broken crockery and the remains of an old medicine bottle, and we ran into another collector looking for pieces to make jewelry for an upcoming show. She told us the beach was her favorite and that when we returned, to come back at low tide. Since that first visit, Hoopers has continued to give its treasures to me, and I am always grateful. visitdorchester.org
– Niambi Davis
Best Place to Spend 4th of July: Cape Charles, Va.
The town of Cape Charles has experienced a renaissance in recent years. This former Bayside railroad terminus and ferry port has become a hot destination for close-to-home Chesapeake vacations while retaining its small-town charm. No time is better to visit than the 4th of July. The beach, located within walking distance of the entire town, is more than ample enough to never feel crowded, even on busy holiday weekends. Craft and food vendors set up nearby. On the morning of the 4th, there is a parade featuring dozens of golf carts (the locals’ preferred means of getting around town) and bikes festooned with enough red, white and blue to satisfy even the most patriotic onlooker. The fireworks are outstanding for a mid-sized community, and boaters can get a slip at the harbor and take it all in from the comfort of their very own decks. visitesva.com
– Robert Gustafson
Best Haunted Rock: Moll Dyer Rock
As the story goes, Moll Dyer was a 17th-century immigrant to Southern Maryland. When an outbreak of flu hit the community, she was blamed for witchcraft and chased out of her home by angry townsfolk on a bitter February night in 1698. She died alone in the woods, frozen to a stone, and her handprint remains on the stone to this day. You can see it, now protected under plexiglass outside the St. Mary’s County Historical Society, as a monument to the need for tolerance and understanding from a woman unjustly accused. stmaryshistory.org
– Susan Moynihan
Best Walking Tour/Picnic: Culinary Quest at No Thyme to Cook Solomons, Md.
No Thyme to Cook is a cooking school offering hands-on classes as well as mixology sessions and events like wine festivals and themed dinner parties. Their newest creation is Culinary Quest, where they send participants out on an app-guided combination walking tour/quiz through the historic downtown. Answer each question correctly to get your next clue as you make your way around, stopping at various purveyors to gather goodies for your well-earned picnic reward. nothymetocook.com
– Susan Moynihan
Best Island for Birding: Eastern Neck National Wildlife Refuge
This is one of my favorite go-to places to take a walk or a leisurely bike ride. Eastern Neck National Wildlife Refuge is a 2,285-acre island located where the Chester River opens up onto the Chesapeake Bay. Its fields and forests are surrounded by salt marshes fringed with loblolly pines. The Audubon Society as designated the refuge as one of its “Important Bird Areas.” More than 240 bird species visit the refuge through the seasons, along with small mammals and many other wildlife species.
If you go in the winter to see the migratory waterfowl, you’re likely to see large flocks of tundra swans rafted up right by the little bridge leading over to the island. Winter is the only time you’ll see such a sight, but it’s also a grand season for a walk in the woods, and Eastern Neck has several trails through an interesting variety of habitats, from oak-and-holly woods to glades of loblolly pine, past salt marshes and through open meadows and fields. Each has its own character and its own set of critters. fws.gov/refuge/eastern-neck
– Jefferson Holland
Best Public Dog Beach: Matapeake Dog Beach, Md.
There aren’t many beaches where you can play with your dog off the leash. Queen Anne’s County’s dog beach at Matapeake is located next to the county’s one public swimming beach. The path to the dog beach runs along the outside of the fence and into the loblolly pines. About halfway down the mile-long trail, the path descends a steep bank and the forest changes from pines to yellow poplars and other hardwoods. It soon opens up onto a breathtaking panorama of the Chesapeake Bay. That view alone is worth the trip. The full 4.5-mile length of the bridge forms the northern horizon, while the massive stone jetty protecting the NRP boat basin juts into the Bay along the southern horizon. qac.org
– Jefferson Holland