Meandering Through Chesapeake Bay

The Mid-Atlantic region’s Chesapeake Bay is the largest estuary in the United States and one of the top cruising grounds in the world. Two hundred miles long, fed by 150 rivers and creeks, and sheltered from the Atlantic by its Eastern Shore peninsula, the Bay has a long and wonderfully convoluted coastline that’s a joy to explore.

Its waters are a complex stew of fresh- and saltwater that creates a uniquely rich tidal laboratory for an incredible range of wildlife. It remains a productive fishery (despite its various environmental troubles), long famous for its blue crabs, oysters, and striped bass. While its Western Shore is far more developed than the still-rural Eastern Shore, on both sides of the bay you can find places essentially untouched since the Algonquian-speaking Native American tribes owned its pristine shores.

The Chesapeake is generally shallow (21 feet on average), so you’re likely to go aground sooner or later, but it’s almost always sandy or soft when you do. Tides and currents here are generally mild, depending on wind and location. Unwound, the Chesapeake’s shoreline would stretch for almost 11,700 miles (longer than the entire West Coast of the United States) and, for boaters, it’s filled with seemingly endless destinations.

With a canvas this big, where to begin? It turns out an excellent way to understand the bay is to look at it the same way that fish, crabs, and oysters do – by the three salinity zones that make up its water:

The Upper Bay is the freshwater zone, with little to no salt (up to about 0.3%). It runs from the mouth of the Susquehanna River in Maryland – the bay’s headwater and primary tributary – to the Chesapeake Bay Bridge near Annapolis. It’s the narrowest part (less than 3 miles wide), and even in the height of summer you can swim up here without worrying about sea nettles, since jellyfish don’t like freshwater. Boaters will notice a big military presence throughout the Chesapeake, and up here it’s Aberdeen Proving Ground north of Baltimore, the Army’s massive R&D testing range for heavy military ordnance and explosives.

The Mid-Bay is the brackish zone, with a medium amount of salt (about 1%), and gradually widens from the Chesapeake Bay Bridge south to the Rappahannock River. This is the ideal mix for the bay’s famed oysters and blue crabs, though both tolerate a wide range of salinity. Home to the U.S. Naval Academy, the Mid-Bay is the largest and most popular segment for both sail and powerboat cruisers. Part of this area, the remote Northern Neck on the Western Shore, was once called “the Barbary Coast of the Chesapeake” during the deadly Oyster Wars from the mid-1800s to the 1950s.

The Lower Bay runs from the Rappahannock River to the mouth of the bay itself, between Cape Charles and Cape Henry. The waters here become as salty as the open ocean (up to about 3.5%) and are occasionally visited by whales and sharks. Here at the bottom of the bay, in the Elizabeth River, is sprawling Naval Station Norfolk – the largest naval base in the world and homeport to the Navy’s Atlantic Fleet of aircraft carriers, subs, and other warships. Whatever you’ve forgotten about the maritime rules of the road, remember this: The 500-yard security exclusion zone surrounding Navy vessels is no joke down here – especially in the narrow Elizabeth River – where tense confrontations routinely occur between armed picket boats guarding the ships and clueless recreational boaters who stray too close.

So, with salinity as a guide, here’s a cruising overview of Chesapeake Bay, from top to bottom.

THE FRESHWATERS OF THE UPPER BAY

Baltimore is the main hub for both power- and sailboat charters up here, although some of these charter companies also operate in Rock Hall on the Eastern Shore. The Inner Harbor has the Baltimore Aquarium and numerous floating or waterfront museums (such as the USS Constellation, the submarine USS Torsk, a Coast Guard cutter and lightship, and the Seven Foot Knoll Lighthouse), all linked by water taxis. Still standing at the very narrow entrance to the Inner Harbor, as it did during the failed British attack during the Battle of Baltimore in 1814, is Fort McHenry, one of the most visited national monuments in the country.

North of the Patapsco River, the Chesapeake gets narrow and shallow. However, the Eastern Shore up here has some good anchorages, particularly in the Sassafras River. Above that is the Chesapeake and Delaware Canal, a 14-mile connection between Chesapeake and Delaware bays and the point where flocks of snowbird cruisers enter the Chesapeake each fall as they migrate south. The cozy hamlet of Chesapeake City is the only harbor in the canal near the bay, with an interesting canal museum and a few good restaurants.

At the far northern end of the Chesapeake is the historic town of Havre de Grace, sitting at the mouth of the Susquehanna River. Powerboats prefer this port of call because it’s reached by a long, narrow, shallow channel.

From Baltimore, a popular circuit is to cross the bay to the charming fishing village of Rock Hall on the Eastern Shore, which has a wonderfully sheltered anchorage in Swan Creek, several very good marinas and restaurants, and the nearby Eastern Neck National Wildlife Refuge – a great place to kayak.

THE HISTORY-RICH MID-BAY

Annapolis may not quite be “the sailing capital of America” as sometimes claimed (Newport, Rhode Island, probably takes that crown), but it’s certainly the boating capital of Chesapeake Bay, with several sail- and powerboat charter options. The two-week Annapolis Boat Show every October is one of the major in-water power and sail shows in the country, with acres of gleaming boats and floating docks jammed into City Dock’s famous Ego Alley.

Annapolis is one of the most historic and beautiful state capitals in the nation, having served temporarily as the national capital, and where Congress ended the Revolutionary War by ratifying the Treaty of Paris in 1783. Its distinctive street plan dates to 1694, and the town has streets lined with unaltered 18th century brick buildings.

And, of course, Annapolis is home to the U.S. Naval Academy (its 338-acre campus, “The Yard,” is open for tours, but check the schedule). During Commissioning Week in May, hundreds of power- and sailboats anchor in the Severn River and Annapolis Harbor to watch the Blue Angels precision flying team as they celebrate the 1,000 newly minted officers who graduate each year. In summer, a warship anchors outside the harbor as a floating classroom, and Academy mine countermeasure ships can be seen on training maneuvers in the bay. Its fleet of Navy 44 sloops, flying blue-and-gold spinnakers, are unmistakable during the racing season.

For boat charters, popular destinations out of Annapolis are north to Baltimore or southeast to the Eastern Shore, especially to St. Michaels on the Miles River and, farther south, Oxford on the Tred Avon River. This route takes you past the iconic symbol of the Chesapeake – Thomas Point Shoal Lighthouse, the last working wooden screw-pile lighthouse on the bay (its iron pilings screwed into the muddy bottom) still in its original location. Lighthouse tours are available through the Annapolis Maritime Museum.

Northern Half of Mid-Bay: St. Michaels, once a major trade and shipbuilding center, has become a high-end tourist town with expensive inns and restaurants and a crowded harbor. Its main attractions are a delightful historic district of immaculately restored colonial houses, the Chesapeake Bay Maritime Museum (with period log canoes, skipjacks, and the Hooper Strait screw-pile lighthouse), and the Crab Claw, one of the best waterfront crab houses on the Chesapeake. Wandering the beautiful streets of St. Michaels, touring the museum, and sitting down to a mess of steamed crabs and pitcher of cold beer is a great summer day on the bay.

Oxford is home to one of the best Chesapeake boatbuilders (Cutts & Case Shipyard) and the country’s oldest privately owned car ferry (Oxford-Bellevue, crossing the Tred Avon).

Today, both St. Michaels and Oxford are among the most charming harbor towns on the Chesapeake, but they get crowded on big weekends. If you prefer solitude on the water, a relaxing place to escape the crush of St. Michaels is nearby Wye River, where you can dinghy ashore at various inlets to hike the Wye Island Natural Resources Management Area. Near Oxford, my favorite remote place is Broad Creek, off the north shore of the Choptank River, which has several branches and some fabulous quiet anchorages that can take days to explore.

Southern Half of Mid-Bay: Solomons Harbor has several excellent marinas and charter outfits and is an ideal base for exploring the southern part of the bay. South of Solomons is the huge Patuxent River Naval Air Station, a major pilot training and R&D center for warplanes and drones. You’re likely to see some interesting things flying around here.

This part of the Chesapeake has much to explore. On the Western Shore below Solomons is the mouth of the Potomac River, the second-largest freshwater source for the bay, reaching up to Washington, D.C. Farther upriver you’ll pass Quantico Marine Corps Base and George Washington’s Mount Vernon plantation.

Other popular boating destinations in this area include St. Mary’s River (on the north shore near the mouth of the Potomac) and Reedville on Cockrell Creek, off the Great Wicomico River. Across the bay on the Eastern Shore are Smith Island (on the Maryland side) and Tangier Island (on the Virginia side), the last two remaining offshore watermen communities on the Chesapeake. Both have rich and unique cultures dating back to the earliest European settlements in America; both are expected to be lost as sea levels rise. These low-lying islands have skinny water, suitable only for boats drawing 4 feet or less.

This part of the Eastern Shore has some of the most remote parts of the Chesapeake. Crisfield, once a rowdy hub of the oyster and crab industries, today is a much smaller and quieter town. Onancock, farther south, has become something of a cultural center and is a charming place to explore by boat. From there, the best boatyard on the lower Eastern Shore is in the small town of Cape Charles, just up from the Chesapeake Bay Bridge Tunnel that spans the 12-mile-wide mouth of the bay. On the Western Shore at the mouth of the Rappahannock River, popular cruising destinations include Irvington (on Carter Creek, north side) and Deltaville (southern side).

LOWER BAY TO MILE MARKER ZERO

As you enter the southern part of the Chesapeake, the last extensive cruising ground is Mobjack Bay on the Western Shore, which has four major branches to explore. Below there, the waters get thick with American history – and even thicker with military installations:

• At the tip of the York River is Yorktown Battlefield, where American troops and the French navy forced the British army to surrender in 1781, ending the Revolutionary War. Farther upriver is the Yorktown Naval Weapons Station, where Atlantic Fleet ships come up from Norfolk to load munitions before heading out to sea.
• Taking up the entire western side of Back River is Langley Air Force Base, the oldest continuously active air base in the nation. As I discovered one night, you can’t miss Back River if you pass it in the dark – because Langley’s runways are lit up bright as day.
• Approaching Norfolk, you enter the waters of Hampton Roads near the harbor town of Hampton, the major port for civilian boats down here. Hampton Roads is where the USS Monitor and CSS Virginia fought to a draw in their famous Civil War “battle of the ironclads” in 1862, the world’s first contest between self-propelled mechanized battlewagons.
• At the bottom of the Chesapeake, flowing in from the west, is the wide and shallow James River. On its northern shore is Historic Jamestowne, the site of the first successful English settlement in America. Here you can visit a museum, the carefully reconstructed town and fort, and replicas of the Susan Constant, Godspeed, and Discovery.
• Anchored a bit downstream of Jamestown are what remains of the James River “ghost fleet” of mothballed and rusting supply ships. It is the oldest of the last three National Defense Reserve Fleet sites and once held as many as 800 vessels. Today, fewer than a dozen remain.

For recreational boats, the best stopover down here is Portsmouth’s wonderfully restored and walkable Olde Towne district, which has a deep maritime history and caters to transient cruising boaters. The town offers free overnight docking for vessels 40 feet or less at the High Street Basin; if that’s full, Hospital Point anchorage is located nearby just below Portsmouth Naval Medical Center, the oldest hospital in the naval medical system.

A water taxi crosses the river from here to Norfolk’s waterfront and the Nauticus maritime center, permanent homeport for the massive World War II battleship USS Wisconsin, one of the biggest ever built.

For the countless snowbirds fleeing winter every year, it is here – just off the stern of the Wisconsin, at red buoy 36 in the middle of the Elizabeth River – where the Chesapeake Bay comes to an end. Better known as Mile Marker Zero, this is the start of the Intracoastal Waterway, the thousand-mile-long “ditch” that boaters follow all the way to Florida – a different adventure and another story.