Greg Alexander

Sailing away on the Bay

Mason-Dixon Arrive, June 2005

The Chesapeake Bay’s approximately 4,000 miles of shoreline offer endless opportunities to discover quiet hideaways, exciting ports of call and sleepy, quaint towns rich in history. When the weekend rolls around, sailors look to hit the open waters for some time on the Bay. If you’re looking for a weekend trip on your sailboat, where should you go? Chesapeake City, North East, Annapolis, Baltimore, St. Michaels, Easton, Oxford, Tilghman Island … the list goes on and on. Of course, where you dock your boat and its size will determine where you can go for a two- or three-day trip. As a recent sailboat owner, I’m anxious to explore all the Bay has to offer. So, here are three popular weekend trips that encompass several ports of call.

Baltimore to Rock Hall

If you are leaving from the Baltimore area and want a quick weekend trip, head East across the Bay from Baltimore toward the charming town of Rock Hall, which lies a mere 23 nautical miles from Baltimore’s Inner Harbor. “From the Patapsco River, you can almost see Rock Hall with your bare eyes on a clear day,” says Richard Hopp, sailing enthusiast and member of the Open Seas Yacht Club, a group of Chesapeake Bay boaters. Rock Hall is an easy sail from Baltimore and Annapolis and a good one, especially for beginners. The trip can be done in two to three hours, depending on the weather, of course. This is a perfect distance for a weekend trip, especially if you must work on a Friday (how many times can you call out sick on a sunny Friday afternoon in one summer?) and want to get an early start on Saturday morning.

Rock Hall Harbor, located just north of the Chester River and south of Swan Creek, is protected and close to the open waters of the Bay, making traversing into the well-marked port easy. The numerous marinas at Rock Hall can accommodate the day visitor or overnight guest. The Rock Hall Landing – the closest marina to downtown – is a popular marina with an array of amenities, including electric, showers, pumpout and ice facilities. Additionally, the marina has a swimming pool, picnic and barbeque area, bike rentals and motel or villa accommodations onsite in case you’re not willing or able to sleep onboard your boat. Hopp also recommends The Sailing Emporium to dock your boat. This marina also has gas and diesel pumps, pool, electric, laundry, showers and pumpout facilities. If you need to stock up on marine supplies or need engine repairs, The Sailing Emporium also has these features onsite. “If you don’t want to sleep onboard, Rock Hall also has six or so wonderful bed and breakfasts in town,” says Hopp.

If you leave Baltimore first thing Saturday morning and arrive at the Rock Hall Harbor by lunchtime, there are ample dining options. If crabs are your thing (this is Maryland, after all), head to the Waterman’s Crab House, which has its own docking facilities, for some steamed crabs to be devoured while enjoying the views from the restaurant’s outdoor picnic tables. Other restaurants include the Channel and Osprey Point Restaurant. Hopp notes that the city has an efficient trolley service that runs from the marinas into town to do some sightseeing. The Rock Hall Trolley also makes daily runs into nearby Chestertown, an alternative to sailing to Chestertown via the Chester River, which would make for a long weekend trip, says Hopp.

If you’re a fisherman, Rock Hall's 10th annual Pro-Am Rockfish Tournament is June 10-12 with a $10,000 first prize up for grabs. Rock Hall also has an impressive fireworks show for Independence Day.

Annapolis to St. Michaels

An always-popular sailing trip is the 25-nautical-mile jaunt from Annapolis to St. Michaels, says Mark Cline, who has been sailing the Bay for the past 15 years. Cline notes that the relatively short trip to St. Michael’s allows for enough time to explore the quaint town. Head southeast from Annapolis from the Severn River toward Bloody Point Light, at the foot of Kent Island. Meander around Kent Island’s coastline in the Eastern Bay, which connects the Miles River, Wye River, Prospect Bay and the Kent Island Narrows. The large Eastern Bay is generally deep and long on wind.

To get to St. Michaels, you’ll sail through the Miles River, one of the Eastern Shore’s busiest areas. In the summer, there can be countless boats around St. Michaels, which can be intimidating if this is your first trip here. A good landmark is the Hooper Straight Lighthouse at the Chesapeake Bay Maritime Museum. Luckily, the port area is wide, allowing for the throngs of boats in the warm weather season. There are two main marinas in St. Michaels. Bob Pascal’s St. Michaels Harbour Inn, Marina and Spa is gorgeous and St. Michaels’ only waterfront hotel and marina. The inn has 46 suites and deluxe rooms and a 54-slip marina. If you need overnight hotel accommodations, the inn’s rooms are spacious and offer beautiful, panoramic views of the waterfront. The onsite spa may come in handy after working the lines all day, as well as the Harbour Light Restaurant, which has excellent cuisine (I ate there last summer and had an amazing meal). Another marina option is the St. Michaels Marina, which boasts a 60-slip marina, three onsite restaurants and a swimming pool. Both marinas offer electric, showers, laundry, pumpout, marine supplies, ice and beer.

Many of the town’s waterfront restaurants also provide dockage for their customers, including the famous Crab Claw Restaurant, which is always slammed with crab-loving diners in the summer (try the fried clams, too; they are addictive). Be prepared to pay cash, though – the Crab Claw does not accept credit or debit cards, although there is an ATM machine in the parking lot. The restaurant also has great T-shirts and other crab-related souvenirs to bring back for friends.

While in St. Michaels, brush up on your War of 1812 history, as, according to legend, the town was made famous for being “The Town that Fooled the British” when townspeople tricked the invading British fleet by hanging lanterns on ship masts and in the treetops so that the British would fire cannonballs over the town (only one house was hit, The Cannonball House, which is still a private residence). No trip to St. Michaels would be complete without a stop at the Chesapeake Maritime Museum, which can take a day within itself and is the host to the Antique & Classic Boat Festival, June 17-19).

If you’re lucky enough to have a long weekend or a few “sick days” left, you could chart a course for a side trip from to Oxford, 30 nautical miles from St. Michaels.

Chesapeake City to Havre de Grace

The Chesapeake and Delaware Canal is a magnificent part of the Intracoastal Waterway that dates back to 1829. The 12-mile, 450-foot-wide C&D Canal is government owned, toll free and connects the Chesapeake and Delaware bays. At the heart of the Maryland side of the Canal is historic Chesapeake City. If you reside in the area or find yourself in Chesapeake City, and you’re looking for a short weekend get-away, then head west about 19 miles to Havre de Grace, located near the mouth of the Susquehanna River. The Susquehanna is enormous and contributes more than half of the fresh water of the Chesapeake Bay. Due to the Susquehanna’s size, sailing into Havre de Grace is pretty simple. Overnight slips are available at the Havre de Grace City Yacht Basin, Tidewater Marina, Havre de Grace Yacht Sales & Marina at Log Pond and Havre de Grace Yacht Sales & Marina at Water Street. Tidewater Marina is the closest marina to the center of town, and its ship store carries clothing, hardware, gifts and electronics with prices rivaling discount catalogs.

Havre de Grace, French for “Harbor of Grace,” is a town steeped in history. The 18th century town features historic attractions, quaint shops, antique haunts and dining options aplenty. Stop at the Concord Point Lighthouse, the Maritime Museum or the famous Susquehanna Museum of Havre de Grace at the Lockhouse, which pays homage to a former canal that led north from Havre de Grace to Pennsylvania. Of course, no mention of Havre de Grace would be complete without talking about decoys. Dubbed the “Decoy Capital of the World,” the Havre de Grace Decoy Museum houses more than 1,200 decoys, displayed in various habitats accompanied by audio history. Pick up a decoy for yourself at Vincenti Decoys, 353 Pennington Ave., or one of several terrific antique shops within walking distance. However, shopping in town is not limited to decoys. Downtown boasts a slew of antique and boutique shops, including bookstores, jewelry, art and at end of the shopping district, The House Downtown, which carries sweet-smellies, unique personal gifts and land-lubbing furniture.

When you decide to stop and grab a bite, The Crazy Swede offers great dining, as does the award-winning Tidewater Grille with its picturesque water views. MacGregor’s is another popular stop, as is Coakley’s Pub and Susquehanna Station. Looking for an old-fashioned “tea time” experience? Then, make reservations for an afternoon tea at the Heritage Tea Room, 421 St. John St. If you happen to be in town from June 6-12, be prepared for a more bustling Havre de Grace, as the McDonald’s LPGA Championship will be held at Bulle Rock Golf Course, one of women’s golf’s major tournaments. Another big event is the annual Maritime Heritage Festival at the Havre de Grace Maritime Museum, June 4-5.

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