Written by Capt. John Page Williams

“Heaven & earth never agreed better to frame a place for man’s habitation…Here are mountaines, hils, plaines, valleyes, rivers, and brookes, all running most pleasantly into a faire Bay.” (Capt. John Smith, The Generall Historie of Virginia, New England & The Summer Isles, 1624).

Actually, Captain Smith and the rest of us “come heres” have discovered something the Chesapeake’s native Algonkian tribes have known for centuries. The Chesapeake is what geographers call a drowned river valley, the largest estuary in the United States, and the third largest on Earth, with 11,684 miles of shoreline.

Our Bay formed after the last Ice Age, when rising sea level let the Atlantic flood 200 miles of the lower Susquehanna River. It captured large tributaries that we know today as the Potomac, James, Rappahannock, York, Patuxent, Choptank, Nanticoke, and some 30 more, forming an intricate web of navigable waterways. In 1612, Captain John Smith opened the system to colonial settlement by publishing a map based on his explorations during 1607-09. He covered all the tidal waters in the Chesapeake and its rivers, except for the Choptank, the Eastern Bay complex (including the Miles and Wye), and the Chester. No wonder the Park Service’s Captain John Smith Chesapeake National Historic Trail is 1,800 miles long!

Since then, these waterways have provided natural infrastructure for a land that had no major roads until a century ago. Today, they still fulfill a commercial function, with two of the North Atlantic’s largest ports (Hampton Roads and Baltimore), regional traffic by tug and barge, and “the water business” (seafood harvesting).

At the same time, the Chesapeake’s waters invite recreational exploration in watercraft large and small, under sail, oars, paddles, and power. This is a People’s Bay. A standup paddleboard or kayak or canoe, a paddle, and a PFD are enough to get started, whether on Spa Creek around Annapolis, the Miles River around St. Michaels, or Powhatan Creek behind Jamestown Island, where there’s a bald cypress tree that sprouted before John Smith arrived.

At the other end of the spectrum are cruising grounds for larger boats, whether power or sail. Our Bay has been a Mid-Atlantic hub for passagemakers for more than a century, visiting not only large harbors like Baltimore, Washington, D.C., and Norfolk/Portsmouth but also smaller water towns like Havre de Grace, Chestertown, Crisfield, Onancock, and Urbanna. Adventurous trawlers poke way up the rivers to Seaford on the Nanticoke and Richmond on the James. Many cruising sailors also race, whether in friendly weekend rivalry or hardcore competition. A majority of them cut their teeth in active dinghy classes. Major centers stretch from Annapolis and Oxford to Fishing Bay and Hampton, with smaller but enthusiastic club racing in between.

For those of us with “day boats,” whether skiffs or runabouts, the Chesapeake gives us so much water for exploring, gunkholing, day cruises, sunset-watching, picnics, and tow sports, plus a cornucopia of fishing opportunities. Some of us develop lifelong loves for home waterways, while others take advantage of hundreds of launch ramps.

Even better, the Bay blesses us with four distinct seasons, at least three ripe for boating, within limits of prudence. Even the Chesapeake’s winter, though an acquired taste, invites us out for ventures afloat or walks along favorite beaches. For all of these reasons, we celebrate all that our Best Bay gives us every day.

Best Raft-up

Maryland: Rhode River

A perennial favorite for Middle Bay boaters, even in these times of social distancing, Rhode River raft-ups are popular choices for clubs and others just looking to hang out, swim, and enjoy. Go at the right time and you might even get a show; this year it was the site of Rock the Rhode, with a local band playing to the crowd.

Virginia: Little Bay at Fleets Bay

Just north of the mouth of the Rappahannock River, this popular anchorage is big enough that it doesn’t get too crowded, and a great place to watch the sunset or dinghy ashore to the secluded beach. It’s not terribly protected, but it is convenient to the open Bay and a popular waypoint for travelers.

Best Place to Paddle

Maryland: Rockhold Creek

Part of Rockhold Creek’s popularity may be its proximity to Chesapeake Paddle Sports (see “Best Kayak/SUP Store”), which makes it an easy place to test out a new purchase. But whether you do one of their group tours or strike out on your own, there are plenty of marinas (and a couple of dock bars), as well as a lovely sunset to be seen on Rockhold Creek.

Virginia: Poquoson

This peninsula at the southern end of the Bay offers 87 miles of shoreline to explore, abundant wildlife to check out, and a number of places to put in. The city of Poquoson has also put together a series of “Blueway” water trails to suit the needs or schedule of any paddler.

Staff Pick: Dragon Run, VA

Best Sailing Town

Maryland: Annapolis

The self-proclaimed “Sailing Capital of the U.S.” took a hit this year with the cancellation of the U.S. Sail and Powerboat shows, but it still has plenty to offer, from plentiful boatyards and easy docking to quick access to downtown and the Bay.

Virginia: Deltaville

For a small town, the “Boating Capital of the Chesapeake Bay” offers outsized opportunities to get out on the water, whether you’re looking for fishing tournaments or sailboat races. 

Staff Pick: Hampton, VA

Best Place to Show Off

Maryland: Ego Alley, Annapolis

A narrow channel with dockside bars, easily visible from all sides, adds up to plenty of people checking out your boat—or heckling you from a safe distance, depending on how you perform.

Virginia: Riverwalk Landing, Yorktown

Along with outdoor dining, shops, and a lovely walking spot along the York River, you’ll find 1,200 feet of dock and enough current to make docking interesting.

Staff Picks: Baltimore Inner Harbor & Hampton River

Best Powerboat Rental  

Maryland: Waypoints Annapolis

Formerly Cruise Annapolis, Waypoints offers charters on a fleet of sailboats, but also rents a pair of Jeanneau Power NC 33s for those interested in a less strenuous day on the water.

Virginia: Carefree Boat Club, Newport News

Not to knock boat ownership, but sometimes it’s anything but carefree. The Carefree membership model is a little different than just renting a boat for a few days, but it takes care of a lot of the hassle and allows for unlimited usage of their fleet.

Best Sailboat Rental 

Maryland: Haven Charters, Rock Hall

Rock Hall’s Haven offers a couple dozen yachts for the occasional sailor, ranging from a Catalina 350 to a Beneteau 51.1, and makes a convenient starting point for voyaging to many Upper Bay attractions.  

Virginia: Norton Yachts, Deltaville

On the Lower Bay, Norton offers a small fleet of sailboats in the 30- to 50-foot range for cruising to dozens of anchorages.

Best Tour Boat Operator 

Maryland: Blue Crab Charters, Rock Hall

Blue Crab’s Island Girl, a Morgan 43 center cockpit cruiser, offers 90-minute cruises five times a day, seven days a week, including a sunset cruise. An extra $20 gets you a Waterman’s Crab House crabcake platter for the full Rock Hall experience.

Virginia: American Rover, Norfolk

The American Rover is a 135-foot, three-masted topsail schooner, Coast Guard certified to carry 129 people (limited to 65 passengers this year for social distancing). They offer two-hour harbor and sunset cruises, as well as special events booking and private event rental based in Norfolk.

Staff Pick: Schooner Woodwind, Annapolis

Best Anchorage

Maryland: Wye River

A number of anchorages dot this river, with the deepwater Shaw Bay probably the best-known. But the 16 miles of the Wye hold many other spots along the undeveloped shore, and the careful gunkholer will be rewarded.

Virginia: Corrotoman River

Just off the Rappahannock, the Corrotoman River offers several secluded anchorages. It’s close to Irvington and just across the Rappahannock from Urbanna. Sandy Point and Bells Creek, on the Eastern Branch, are popular hurricane holes, or if you’re in search of solitude, try the deeper water of Western Branch Cove.

Best Resort Marina

Maryland: Herrington Harbour South, North Beach

When the marina is the destination, the amenities make it worth the trip. Herrington Harbour South offers pools, beaches, a restaurant, a market—pretty much everything you or your boat need for a relaxing getaway, with easy Bay access.

Virginia: Tides Inn, Irvington

Stay on the boat or book a room; either way, you can enjoy bike, kayak, and SUP rentals; pool and beach access; and lawn games (life-size chess!). And check out the water views and locally-sourced cuisine at their Chesapeake Restaurant & Terrace.

Staff Picks: Haven Harbour Marina, Rock Hall, and Coles Point Marina, Hague, VA 

Best Clean Marina

Maryland: Herrington Harbour North, Tracys Landing

Come for the amenities including pools and a tiki bar, but know there is plenty going on behind the scenes as well to make the Bay cleaner and greener, like marsh projects, dustless sanding, and oil recycling.

Virginia: Riverwalk Landing, Yorktown

After a 1985 hurricane left them with a clean slate waterfront-wise, Yorktown planners took the time to rebuild and revitalize the area, including a commitment to protect the York River. That applies to the landscaping and groundskeeping, as well as their piers, with 1,200 feet of docking space, pumpouts, water, and electricity. 

Best Marina for Transients 

Maryland: Shipwright Harbor, Deale

Shipwright gets high marks for its beautiful location off Herring Bay, as well as its amenities (including bathhouses, pool, and laundry) and friendly staff, making it a tranquil stop for boaters transiting the Bay and a repeat destination for weekend cruisers.

Virginia: Riverwalk Landing, Yorktown

Offering overnight stays for transient boaters, with electrical and water hookups as well as pumpout facilities and showers, Riverwalk makes a great stop on the York River, with easy access to the Bay and a prime spot for the various concerts and events held along the water.

Staff Pick: District Wharf, Washington DC

Best Overall Marina

Maryland: Herrington Harbour South, North Beach

Guests rave about the food, the pool, the friendly staff, and the views, pushing Herrington South to the top of multiple Best of the Bay categories every year, so it’s only fitting that their fans drove them to the top spot this year.

Virginia: Stingray Point, Deltaville

A favorite of CBM staff, Stingray Point proved a favorite with readers too this year. With easy access to the Bay, as well as secluded creeks and rivers, this Deltaville marina says it is “dedicated to providing a quiet, secure, and scenic facility for annual slipholders where the joys of boating and sailing can be realized without the intrusions of commerce.” Sounds pretty good to us.

Staff Picks: Campbell’s Boatyards, Oxford, MD & Harbor East, Baltimore, MD

Best Dockmaster

Maryland: Tyler Rice , Herrington Harbour South, North Beach

Virginia: Capt. James Scruggs, Riverwalk Landing Piers, Yorktown

Best Fuel Dock

Maryland: Rhode River Marina, Edgewater

Virginia: Bluewater Yachting Center, Hampton

Staff Pick: Annapolis City Marina

Best Working Boatyard

Maryland: Bert Jabin Yacht Yard, Annapolis

Virginia: Zimmerman Marine, Deltaville

Best Engine Mechanic 

MarylandRhode River Marina

Virginia: Deltaville Boatyard

Best Marine Electrician

Maryland: Marine Technical Service HHN, Deale 

Virginia: Zimmerman Marine, Deltaville

Best Canvas Shop

Maryland: Canvas Connection, Tracys Landing

Virginia: Ship’s Tailor, Deltaville

Best Sailmaker

Maryland: Quantum Sails, Annapolis

Virginia: Evolution Sailmakers, Deltaville

Best Learn-to-Sail Program 

Maryland: The Sailing Academy, Tracys Landing

This sailing school has a course that’s great for beginners: “Try Sailing.” That’s it— just try it! You don’t need a wealthy friend, or a boat of your own, to give it a shot. If you like it, maybe sign up for one of their beginner classes; if not, hey, no problem. 

Virginia: Norton Yachts, Deltaville

Norton really does it all: charters, sales, service, and an American Sailing Association-certified sailing school to get you ready for all that. Norton estimates that 40 percent of the students in their two-weekend classes arrive with no experience, and the classes are limited to four students, so everybody gets plenty of hands-on time.

Best Beginner Powerboat Classes

Maryland: Annapolis School of Seamanship

It’s always a little embarrassing when CBM’s sister company wins, but they were overwhelmingly chosen by the voters. For what they do, from Junior Captains to Women at the Wheel to captain’s licenses, they’re really the best game in town, and we’d say that even if they didn’t sign our paychecks.

Virginia: Deltaville Yachting Center

They aren’t a full-time school, but DYC has a vested interest in getting people out on the water and keeping them safe once they’re there. To that end, they offer a two-day Boater’s Boot Camp (with the Richmond Sail & Power Squadron) with classroom and onboard instruction to get you started.

Best Powerboat Race 

Maryland: Cambridge Classic Powerboat Regatta

At more than 100 years old, the country’s longest-running powerboat races were cancelled for 2020, but hopefully they’ll come roaring back next year.

Virginia: Cocktail Class Racing, Urbanna

Another victim of the COVID pandemic, we didn’t get to see people cram themselves into these tiny wooden racers this year. But clearly our readers missed them, and we’ll be looking for them to round the turn throwing up a roostertail of wake next year.

Best Distance Sailboat Race 

Maryland: Governor’s Cup, St. Mary’s City

Virginia: Leo Wardrup Memorial Cape Charles Cup

Best Sailboat Regatta 

Maryland: Helly Hansen NOOD Regatta, Annapolis

Virginia: Southern Bay Race Week, Hampton Roads

Best Kayak/SUP 

Maryland: Chesapeake Paddle Sports, Deale

Virginia: Patriot Tours & Provisions, Yorktown

Best Fishing Charter 

Maryland: Tom Weaver, Annapolis

CBM readers will be familiar with Tom Weaver, a longtime friend of the magazine, and it turns out a lot of you like him too. The votes poured in for this guide, sailor, boatbuilder, and all-around Bay pirate.

Virginia: Capt. Puddin’ (G&G Charters), Deltaville

This year’s winner runs day-long fishing trips on either the 43-foot deadrise Karen Lynn (six passengers) or the 55-foot Lucky Lady (41 passengers). They both get high marks for fishing, but also for the crew and the Cap’n.

Best Light Tackle Guide

Maryland: Tom Weaver, Annapolis

Despite being a New Zealand transplant, Weaver has clearly found a home in the Maritime Republic of Eastport, winning both light tackle and general fishing guide categories by a nautical mile. 

Virginia: Capt. Chris Newsome, Mathews, VA

Tidewater native Chris Newsome has been a saltwater fly and light tackle guide for more than two decades, and claims he took up fishing at the tender age of 15 months. That’s tough to fact-check, but he has built a career on the Bay doing what he loves.

Best Tall Ship 

Maryland: Pride of Baltimore II, Baltimore

These are tough times for tall ships, with COVID restrictions putting a halt to travel and groups, two things necessary to the operation of a large sailing vessel. But Pride has weathered storms before, and readers want to see those raked masts sail on.

Virginia: Schooner Alliance, Yorktown

Yorktown’s own three-masted schooner Alliance has been daysailing from Riverwalk Landing since 2005, with summers spent in the Caribbean. This year put a serious dent in the schedule but they’ll be back out cruising when the weather warms up.

Best Boater’s Bar

Maryland: Tie: Skipper’s Pier, Deale/Boatyard Bar & Grill, Annapolis 

It’s tough to argue with either of these choices, with perennial best crabcake winner Boatyard on the one side and cream of crab soup winner Skipper’s on the other. Then again, they’re pretty close to each other, so theoretically you could hit both of them.

Virginia: Cutty Sark, Norfolk

This is a sad one, as the Virginian-Pilot reported at the end of September, “The Cutty Sark, maybe the last great Ocean View waterfront dive, closes this week after 60 years.” And so, after being buffeted by storms and drunken patrons, after staying open with waist-high flood waters, a great Chesapeake dive bar closes its doors. Pour one out.

Best Place for a Family Cruise

First place:  Hampton, VA

Hampton gets pride of first place here for more reasons than I’ve got room to mention, but let’s try a few. Hampton is a short easy trip up the Hampton River and comes with several good marinas, a classic carousel, an air and space museum, tour boats, parks, and an entire tree-lined, brick street populated with small, local restaurants. It’s also uncongested and relaxing for the grown-ups. Finally, just around the corner, it has historic Fort Monroe, with its own marina, anchorage, beaches,
and restaurants. 

Second place:  Baltimore, MD

I’m giving Baltimore the edge for second place here for its activity-rich waterfront, its cool neighborhoods, Fort McHenry, the Aquarium, and the ballpark at Camden Yards. In addition, Baltimore’s three distinct waterfront neighborhoods—Inner Harbor, Fells Point, and Canton, each with its own marina—make it a three-destination-in-one family cruise.

Third placeThe Wharf, Washington DC

The only reason I’m relegating this colossus of tourism to the number 3 spot is that it’s a bit of a hike up the Potomac River—but one that is well worth the trouble, I believe I’ve mentioned approximately 137 times. Washington Channel’s new Wharf, with its restaurants, shops, entertainment venues, delightful views, fish market and marinas, is a family destination in itself. But its location within walking distance of the Smithsonian, the monuments, a Metro stop, and even a grocery store make it by far the best way to visit the city. Think Cherry Blossom Festival next spring. If you don’t have a boat, get one just to make this trip!

Best Place to Nearly Run Aground

Running aground is as easy as falling off a log. Here are three of my favorite places to do it.

First place:  Knapps Narrows

For five or 10 minutes after Knapps Narrows has been dredged, you and I probably would be fine anywhere along this busy shortcut between the Bay and the Choptank River. But after that, not so much. Coming out of the Choptank this spring, for example, I thought I things were going well until I looked down at my depth-sounder and saw I had all of six inches under my keel. Maybe it’s just me.

Second place:  Leaving Queenstown Creek

This time I know it’s not just me. I’ve heard the stories. Entering this Chester River tributary is not too bad. You just line up the tall pine with the water tower, then be sure you stay well off the long shoal (and lovely beach at low tide) to port before turning into the deep anchorage behind it. Coming back out is the snare that catches the unwary and carefree, who tend either to misjudge the length of the shoal or fail to look over their shoulder to line up the dead reckoning markers. I’ve hit ground here twice.

Third place:  Leaving National Harbor

There is something about the devil-may-care attitude we adopt when leaving a place that catches us time and again. The entrance to National Harbor follows the shoreline of Smoots Bay all the way to the Gaylord Convention Center dock. Easy enough. But later, when following the markers out, people overlook the last two marks and instead shoot out toward the Potomac, only to find themselves in shoal water. Obviously, I’m speaking from experience here. Can you say back up?

Click here to check out last year’s winners.