My favorite place to retreat in a small boat is the Wye River, on Maryland’s rural Eastern Shore. The Wye’s 16 miles of deep channels, unspoiled shoreline, and uncountable marshy tributaries offer a lifetime of gunkholing enchantment. The nearest land-mark is the former shipbuilding and oyster-fishing hub of St. Michaels, now a destination for yachtsmen and tourists.

Launch in St. Michaels after a turn through the magnificent Chesapeake Bay Maritime Museum, which has a wonderful small-craft collection. Just north of St. Michaels on the Miles River, you’ll pick up the entrance to the Wye, guarded by a nasty shoal that reliably filters the lubbers. Once you’ve negotiated the narrow approaches to the Wye, turn east into Shaw Bay, which has good holding for larger boats and is a great staging spot for dinghy exploration.

Three small wooden boats sit anchored near a tree-lined shore as a group of people set up camp, and a map of Wye Island and nearby bodies of water.D. Turner Matthews

Several participants in last year’s Mid-Atlantic Small Craft Festival at the Chesapeake Bay Maritime Museum in St. Michaels sailed together on a camp-cruise around Wye Island.

The Wye River describes a rough lowercase “b,” the vertical leg running north–south, with Wye Island contained in the loop of the “b.” Smaller boats can spend an unforgettable weekend circumnavigating the 2,800-acre Wye Island, which is mostly a nature preserve, with encrustations of mansions at discreet intervals. A 10′-high bridge connects Wye Island to the mainland, allowing our sort of boat to dip the mast and pass safely.

The comparative lack of development limits silting, so much of the Wye River is 10′ to 40′ deep. The forested shoreline helps keep the river uncommonly clean and clear as Chesapeake waters go. Wye River crabs are famous all over the world, and a well-placed trap or two will yield a feast during the hot months. The Chesapeake region smolders in the summer, but the Wye River’s appeal multiplies in the cooler months.

Huge ancient oaks and hickory trees line the high banks of the upper reaches, many of them predating English settlement of the area in the 1630s. The Wye River autumn colors rival the best of the Catskills, and with the yachties gone home for the year, small-boat cruisers have this wild Chesapeake paradise mostly to themselves.

Resources

Queen Anne and Talbot County park facilities and launching ramps:

Chesapeake Bay Maritime Museum, 213 N. Talbot St., P.O. Box 636, St. Michaels, MD 21663; 410–745–2916

Ready to plan your next small boat cruise?

Read our guide on choosing the right destination for your trip where we share some other top small-boat destination ideas.