St. Michaels/Oxford
Tilghman Island
Waterfront Living in Style

By Nancy and Richard Woodworth

Along the languorous shores of the Miles River, not far off the Chesapeake Bay, the historic town of St. Michaels has turned waterfront living into high style. The Eastern Shore's most upscale address is a mecca for visitors and second-home owners, some of whom eventually become year-round residents.

Tucked off the beaten path down a peninsula heading toward the bay and Tilghman Island, St. Michaels has long been known by yachtsmen and by affluent retirees who settled here for watery pleasures and a slower pace not far from the big cities. But it has really been discovered only in the last decade or so. Large new inns have emerged, trendy restaurants and shops have opened, and waterfront properties now sell at a premium.

Today's St. Michaels, still small and rather self-consciously quaint, is a far cry from that of a generation ago – before the Bay Bridge opened up the Eastern Shore to outlanders, before James Michener wrote Chesapeake in a rented house along the Miles River, and before the Chesapeake Bay Maritime Museum evolved into a major tourist attraction.

The first settlers in 1632 called its landlocked harbor "Shipping Creek," an apt reference for a place that would become a busy trading and shipbuilding center. Around the first Episcopal Church, named for St. Michael the Archangel, developed the town that took its name.

During the War of 1812, St. Michaels staged the first blackout in recorded history. British warships gathered on the Miles River to shell this coveted target. Townspeople darkened their homes and hung lanterns in the treetops to trick the invaders into aiming high. When the shelling ceased, the ploy had worked; only the now-famous Cannonball House was hit. St. Michaels had earned a place in history as the town that fooled the British.

Now the year-round population of 1,500 is easily matched by visiting yachtsmen and landlubbers on summer weekends, and by even more decoy collectors and duck hunters in fall. A few skeptics pass off St. Michaels as something of a stage set – mainly fronts and no backs, at least along Talbot Street, the only thoroughfare. They obviously have missed the side streets, the boatyards, the undulating waterfront and the surrounding countryside that better reflect the old St. Michaels, one of America's earliest port towns.

Nearby Tilghman Island and Oxford beckon as well.

Material excerpted from Inn Spots & Special Places / Mid-Atlantic, by Nancy and Richard Woodworth. Copyright 2003.

Wood Pond Press
365 Ridgewood Road
West Hartford, CT 06107
Phone: (860) 521-0389
Fax: (860) 313-0185
© Copyright 2008
All rights reserved.

E-mail feedback to:
woodpond@ntplx.net

Home page | Full destination index |
About Wood Pond Press | Ordering Information | Restaurant of the Week | Inn of the Week |
Book of the Month | Getaway of the Month |