This fall, plan your escape to Michener’s Chesapeake with a weekend in Tilghman Island, Maryland on the pristine shores of the Choptank River. Tilghman Island is a scenic 20 minute drive from St. Michaels, and remains a true working waterman’s village with excellent fishing and fresh seafood. The original skipjacks, the first commercial sailing fleet in North American, are on display at Dogwood Harbor. Captain Wade Murphy, pilots the famous Skipjack Rebecca T. Ruark, circa 1886, on 2-hour sails, 7 days a week in season.
For very reasonable rates you can stay at a family guesthouse or one of the charming Bed & Breakfasts like the Lazy Jack Inn. Romance seekers might prefer the lovely, secluded Black Walnut Inn, nestled in acres of pine woods and marshes, and surrounded on three sides by the Chesapeake Bay. Walking along the grounds of this private resort feels like the only inhabitants sharing your space are the great blue herons and the wild eagles.
If you want luxury and elegance, there are close-by resorts which offer an abundance of fine dining, sports and entertainment. Check out Inn at Perry Cabin or Harbourtowne, stand-alone resorts situated on the water catering to the couple or family who wants to be pampered with first class service and accommodations.
Beginning anglers can join a private fishing charter or if it’s warm enough, rent a kayak or jet ski at Knapp’s Narrows Marina to tool around the extensive shoreline. Visit the many lighthouses on an MV Sharps Island expedition–they have sunset cruises, all day cruises and even an overnight in Onancock, on Virginia’s Eastern Shore.
After a day of wind and spray, your appetite will be whetted for fresh seafood caught by the local fisherman. Harrison House, perched on the bay, is a friendly, family-style restaurant with homemade sides grown locally like fresh corn and tomatoes or other vegetables grown seasonally. Landlubbers can order the pit beef, but most people come for the crab cakes or steamed crabs in season. Or for waterfront, outdoor dining, try Marker 5 Restaurant & Tiki Bar.
On your way, stop by the chic town of St. Michaels; there are at least a dozen adorable boutiques and the Chesapeake Bay Maritime Museum worth a look. The energetic can rent a bike for the 15 mile ride to St. Michael’s to get their shopping fix or quench their hunger with lunch on the water at one of the cafes along the shoreline. The roads are maintained for bikers and the local authorities work to protect the safety of the route. The trails are completely flat and very scenic. In St. Michaels, visitors can tour the Audubon Sanctuary, take a catamaran ride, or test the products at the St. Michael’s Winery. Bike rentals are available in Tilghman and St. Michaels year-round.
Saturday, October 18 is Tilghman Island Day, an annual celebration where visitors can party side-by-side with the natives to feast on crabs, oysters and clams. You can tip some beers with the local fire department boys or hear some bluegrass. This annual festival is often at the peak for enjoying fall foliage.
To head to Tilghman, drive east on Route 50 to the Bay Bridge. After you pass over this three mile expanse, you immediately begin to feel the calm settle over you as you absorb the pace and hospitality of these water towns of the Eastern Shore. Continue through farmland and tobacco fields past the driveways of antebellum mansions with names like the Wild Goose Perch.
Some towns along the way, like Wye River, are worth a stop to see the Old Mill in action and buy some of the best wheat milled flour ever made. Continue to make your way to the Bay again heading toward Easton, worth another brief stop if you want to pick up some picnicking supplies for your day on the water. Take Route 322 through St. Michaels, and then further East until the land stops. At Tilghman you’ve arrived in what is still an authentic, unspoiled town on the Chesapeake Bay.