There is but one entrance by sea into this country, and that is at the mouth of a very goodly bay, 18 or 20 miles broad… Within is a country that may have the prerogative over the most pleasant places known, for large and pleasant navigable rivers, heaven and earth never agreed better to frame a place for man’s habitation. —Capt. John Smith, 1608
Along its 200-mile length you’ll find rich landscapes ranging from marsh grass-speckled white sand beaches to scenes of industry and urbanization. Some parts are so remote and wild that you’d have to strain to find any evidence of humanity, while other parts are so crammed with people that you’d be hard-pressed to find any natural shoreline. It’s this diversity in landscapes and scenes, along with a long boating season, that makes the Chesapeake Bay one of the finest cruising grounds in the world.
The Chesapeake was first thoroughly explored in 1608 by Capt. John Smith aboard a 30-foot wooden sailing shallop over the course of two voyages and four months. Today, the Bay may not be as remote and wild as it once was, but it still warrants exploration by curious cruisers. As the cliché goes, you truly could spend a lifetime here and never see each of the 11,684 miles of shoreline. Keeping that in mind, it’s definitely better to break the Bay into more manageable chunks, one of the finest of which sits in the Middle Bay area between Baltimore and Solomons, Maryland.
In this area you’ll see industry and history, commerce and crabs, and a variety of unique scenery. The cruising season runs between April and late October and you’ll find weather conditions that are mostly benign throughout, save for afternoon thunderstorms that can pop up on hot, steamy summer afternoons. In addition, the Chesapeake is generally forgiving of mistakes, too. Its bottom is soft mud and sand, and protection, in the form of beautiful creeks, coves, and gunkholes, is usually right around the corner. The itinerary can be run either north to south or vice versa, depending on your Bay entry point, but we’ll start our run from the north, in Baltimore.
(NOAA Charts 12278, 12281)
Baltimore is as fine an industrial city as you can find to explore on the Chesapeake. Replete with the remnants of old steel factories, Baltimore is one of the busiest cargo and automobile ports on the East Coast, it conveys the feel of a genuine working waterfront. You’ll hear Baltimore referred to as “Charm City” quite often; it’s a relic from a long-past campaign to promote the city’s image. Also listen for “hon;” it is a cultural term of endearment in Baltimore. “Is that all for you today, hon,” a waitress might ask you. I say, “Enjoy the cruising scene in Baltimore, hon.”
Cargo ships, cruise ships, and tugs are all part of the scene here and bear watching as you proceed up the Patapsco from the main Bay channel. As you’re headed upriver near Lazaretto Point, about three miles after you pass under the Francis Scott Key Bridge carrying Interstate 495 traffic, Fort McHenry will be viewable to port. It was here in 1812 that Francis Scott Key witnessed the British bombardment of the fort and penned The Defence of Fort McHenry. The poem would later be renamed The Star-Spangled Banner before becoming the lyrics for this nation’s anthem. Back at the Francis Scott Key Bridge, a nun buoy with the stars and stripes painted on it marks the spot where Francis Scott Key wrote those immortal words.
The majority of the marina facilities in Baltimore are located either on the north side of Northwest Harbor just past Fort McHenry (to starboard on entry), or farther upriver at the Inner Harbor. While the Inner Harbor marinas will provide better access to downtown and some of the more touristy attractions, Northwest Harbor marinas are closer to the Fells Point, Canton, and Little Italy neighborhoods, all of which have excellent dining choices. Either way, water taxis can get you to and from either location for only a few bucks. As with any of the greater Chesapeake destinations, slip reservations are a must on weekends and holidays. Anchoring is available off the charted numbered “pier” complexes west of the National Aquarium, but the holding is poor and nighttime lights and sounds can keep you restless.
There’s hardly any limit to the things you can see and do in Baltimore and the surrounding area. In the immediate Inner Harbor area there’s the Maryland Science Center, National Aquarium, Federal Hill, and Inner Harbor’s shopping and dining scene. Those are worthy places to investigate, but it’s more fun getting off the beaten path a bit. Fells Point and Camden, which are sandwiched between the Northwest Harbor and Inner Harbor marinas, both have an eclectic mix of pubs, bars, and restaurants serving everything from local seafood (famous crab cakes) to more exotic fare. You’ll be thankful you visited here, hon, when the time comes to point south toward Annapolis, Maryland’s capital city.
Southbound out of the Patapsco River, the twin Chesapeake Bay bridges will come into view as you approach the narrowest point of the Bay between Sandy Point and Kent Island. About four miles southwest of the bridge, the cupolas, sailboat masts, and U.S. Naval Academy waterfront that make up the Annapolis scene will appear.
(NOAA Charts 12278, 12282, 12283)
There are a few notable things about Annapolis besides its being the self-proclaimed sailing capital of America, home of the United States Naval Academy, and the seat of government for the state of Maryland. What you may not know is that it was the capital of the United States from 1783 to 1784, and that General George Washington resigned his commission here in 1783. Besides being ripe with history, the entire town seemingly ebbs and flows with the water, making it a superb destination for cruisers.
Even though Annapolis lies on the Severn River, Spa and Back creeks are the primary waterways used by boaters visiting the city. Spa Creek runs off the Severn toward Annapolis Harbor and the city’s downtown, where most of the action and energy bustle. The somewhat quieter Back Creek is situated just to the south of Spa Creek on the shores of what locals call the “Maritime Republic of Eastport,” an area peppered with marine businesses of all sorts, and some say, a more relaxed way of life. If you pick a marina on the south side of Back Creek, you’ll have to take a land or water taxi to get around the Eastport Peninsula to Annapolis Harbor and its attractions.
As you come into Annapolis, you’ll first notice the forests of sailboat masts. While this is known as a sailing town, there are plenty of marinas in Spa and Back creeks that welcome power cruisers. Reservations are a must in-season, but most marinas will do whatever they can to squeeze you in. City-maintained mooring balls are available in both Spa and Back creeks for $25 a night, and there are some open anchorages in both creeks where you can drop the hook (if you can find space). A water taxi service is available by VHF Channel 68 with fares ranging from $6 to $8, depending on distance. Also, keep in mind that all streets that end at the water are designated as public landings. Many even have dinghy docks and trash disposal facilities for cruisers. Thieves know about the dinghy landings, too, so be sure to lock up your motor and boat before leaving them unattended.
Most everything you’ll want to see in Annapolis is within a mile of the waterfronts of both creeks, so foot travel is the best way to explore this scenic city. Downtown Annapolis is part of the Historic District and adjacent to the U.S. Naval Academy, which is open for foot visitors and provides daily tours. Be sure to bring a government-issued photo ID for entry. Eastport is just over the Eastport drawbridge from downtown Annapolis and is where some of the better restaurants are situated. For good crab cakes, seafood, and a boater’s vibe, try Davis’ Pub or Boatyard Bar & Grill. For great views of the harbor, and more upscale seafood and steaks, try Carrol’s Creek Café, O’Leary’s, or the Chart House.
The harbor has a scene of its own, so you can entertain yourself by watching the parade of arriving and departing vessels—from the mooring field or from Ego Alley, a strip of water that wanders through downtown. It offers boat owners a chance to stroke their egos by parading their vessels in front of a captive audience.
You’ll see folks in canoes and kayaks, people piloting stand-up paddleboards, and, if you’re here on a Wednesday night during the summer, the finish of the Annapolis Yacht Club’s Wednesday Night sailboat races, which finish in the harbor at the Annapolis Yacht Club and Eastport drawbridge.
The next leg of the itinerary offers a change of scenery and the opportunity to explore an area simply known as The Shore by locals, but more widely known as the Eastern Shore. The Eastern Shore is the more rural side of this part of the Bay, dotted with corn and soybean farms, and punctuated by waterfront towns where many folks still make their living from the water.
The 35-mile trip from Annapolis will take you south around Bloody Point, up Eastern Bay, and then south-southeast down the Miles River toward St. Michaels. Along the way, you’ll see many workboats tending to crab traps and trotlines. You’re now deep into crab country.
(NOAA Chart 12270)
This Eastern Shore village proudly calls itself, “The town that fooled the British.”
The story goes that during the War of 1812, St. Michaels residents hung lanterns high in trees farther outside the village, which caused the British to overshoot the main part of town. Several cannon balls did make their mark in St. Michaels, but the move was credited with saving the town. What you’ll find here today is a charming waterfront town with history, scenery, good restaurants, a relaxed vibe, and lots and lots of crab.
The small body of water that branches off the Miles River at Parrott Point is unnamed, but St. Michaels Harbor is how folks refer to it. As you enter the harbor, you can’t miss the screwpile Hooper Strait Lighthouse, which stands at the end of the Chesapeake Bay Maritime Museum grounds. It’s one of the best museums on the Bay.
Past the museum is a wide array of marinas and marine repair facilities, almost all of which are set up for transient guests. There’s room to anchor in the harbor behind Parrott Point in about 10-foot depths, or a little farther north (slightly more exposed) off the Maritime Museum. A water taxi serves the area during boating season.
North Talbot Street is lined with pubs, art shops, antique stores, an Acme grocery, and a good mix of restaurants. There’s even a microbrewery (Eastern Shore Brewing) where you can sample handcrafted beers and see how they’re made. If you haven’t already, this is a great place to try another Maryland tradition—eating hot steamed blue crabs from Chesapeake Bay.
Although it can be a bit touristy, the Crab Claw restaurant is a great place to sit down, order a pitcher of beer, and crack open a couple dozen hard-shell crabs while you check out the scene in the harbor. You’ll find it right outside the entry gate to the maritime museum. Otherwise, walk around, check out the historic architecture, or just lounge in the cockpit and enjoy the good vibes.
The longest leg of the itinerary lies ahead, at 60 miles, as does the last town on our two-week trip: the Lower Western Shore town of Solomons. As you head south down the main channel of the Bay and approach Solomons just north of Cove Point, keep in mind that the Calvert Cliffs Nuclear Power Plant and Cove Point Liquefied Natural Gas Terminal are both secure areas. It’s here, too, that you’ll see extensive log-staked fish traps that you’ll want to avoid.
(NOAA Charts 12270, 12266, 12264, and 12284)
You might feel more like you’re in Maine than Maryland when you round the scenic Cove Point Lighthouse on your approach to Solomons. It’s been warning folks off Cove Point since it was first lighted in 1828. Solomons, like many Chesapeake towns, had its heyday during the height of the oyster rush in the late 19th and early 20th centuries. Today, the economy revolves around tourism and the nearby Patuxent River Naval Air Station at Cedar Point.
You’ll find a good handful of quality marinas in Solomons, and most of them are located on the shores of Back Creek, the western-most of the two main creeks that flow into the Patuxent River at Solomons Island (the other is Mill Creek). It’s easier to just show up here and get a slip, but the early bird usually gets the slip. The smart one makes a reservation.
There is an anchorage in 15- to 16-foot depths for a limited number of boats behind what locals call The Island, which is marked by flashing red “SH” and flashing red “2” just inside the common entrance for Mill and Back creeks. Additional anchorage can be found up Back Creek past red daybeacon 8, and anywhere with space up Mill Creek. Up the Patuxent River from Solomons-proper and past Point Patience are some lovely creeks and coves that offer the solitude-seeking cruiser an excellent opportunity to drop the hook, relax, and soak in the Patuxent’s serene atmosphere. Your access to facilities here will be limited, though. Anyplace you anchor in Solomons is subject to the comings and goings of jet aircraft from the Patuxent Naval Air Station across the river, and yes, it can be quite loud.
Like St. Michaels, Solomons has an excellent museum that displays everything from fossilized shark teeth and whale skeletons to wildlife, boatbuilding, and local culture. You can find it on the northern-most end of Solomons Island Road, the main thoroughfare. This street is also where you can find most of the restaurants in town. If you haven’t checked off eating a Maryland crab cake yet, Stony’s Seafood has a reputation for making some of the best. One last Solomons institution worth mentioning is the Tiki Bar, where you’ll enjoy pulling up a seat just to people-watch right across from the harbor area. Ask anyone where it is and they’ll be able to point you there. The main drag is very walkable, with sidewalks along its length and good views of the Patuxent River waterfront.
While John Smith’s four-month exploration took him from the Bay’s mouth all the way up the Susquehanna River at the top of the Bay (hey, it was an oar-powered sailboat), a two-week Middle Bay adventure offers the opportunity to see some of the best bits, even if they’ve been previously discovered.