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As one of the “last vestiges of quaint old-style towns,” St. Michaels, chartered in 1804, has maintained its 18th-century charm by building itself into a tourist center. Shops, restaurants, bed and breakfasts, inns and a small resort draw visitors curious about life a couple of hundred years ago.

Your trip should include a visit to the Chesapeake Bay Maritime Museum, and a walk past the display in the town square honoring citizens who, during the War of 1812, drove off attacking British troops. A gun used by the town’s defenders is on display.

The golf course at Harbourtowne Resort is an early Pete Dye design. Players can see a little bit of how Dye shapes a course without many of his more contemporary pitfalls. His penchant for railroad ties is apparent. For the average golfer, a pleasant experience on the front turns into the wrath of Pete. Still, from the back tees, the back nine plays shorter than the front (3,123 yards to 3,197 yards) for a reasonable par-70 total.

The town of St. Michaels is also a boating center, with marinas and wharfs situated on the Miles River. It is now one of the top yachting centers in the East, having evolved from a shipbuilding center during the 17th century.


For a place with such a pleasant setting, this city of 25,000 or so has a violent history. Various Native American tribes - Catawba, Cherokee, Delaware, Iroquois and Shawnee - fought over the land as they staked out hunting grounds. The French and Indian War, the Revolutionary War and five battles of the Civil War were also fought here. Cradled in the breathtaking Shenandoah Valley, Winchester now bustles with charm but maintains close ties to it war-filled past.

A spring trip to Winchester could include a day at the famous Shenandoah Apple Blossom Festival, which takes place every May as the apple trees bloom. Visitors can access the Appalachian Trail from Winchester, the nearby George Washington National Forest, the Blue Ridge Mountains and Skyline Drive, unveiling some of the world’s most beautiful country.

The golf at Rock Harbor began on a day in 1996 when Denny Perry, with machete in hand, made his way through a thick stretch of orchard land near his rock quarry. As he explored the dense terrain, he contemplated the placement of fairways, greens and tees. Perry built Rock Harbor, and now he is working on a second course. In the end, holes from each course will intermingle to create two distinct courses. But it is only because of the demise of Carper’s Valley Golf Course that Winchester is again a one-course town.

The city of Winchester is a magnet for history buffs. You can visit the office George Washington used while supervising construction of Fort Loudoun. The spectacular Museum of the Shenandoah Valley, which opened in 2005, tells the story of the art, history, and culture of the great valley.


On the southern end of Virginia’s eastern panhandle, this town is now the definition of quaint. But before golf came along the streets were lined with “For Sale” signs. Bay Creek Resort has put those signs in the garage and increased property values, not to mention business at the shops that make the town worth a visit.

Your trip should include a journey across the Chesapeake Bay Bridge Tunnel, one of the seven engineering wonders of the modern world. The 17.6-mile bridge and tunnel passage across the Chesapeake Bay near where it meets the Atlantic Ocean is the only direct connection between Virginia’s eastern shore and the mainland.

The golf at Bay Creek Resort actually includes two courses , so we stretch our theme on this one. Both the Jack Nicklaus and the Arnold Palmer designs are outstanding. They both have holes exposed to the Chesapeake Bay and inland holes that meander through maritime forest and through the resort community. It will be up to you to decide which one is best.

The town of Cape Charles owes its existence to the railroad and ferry industries, which is the reason the town was founded in the late 19th century. It is now a living tribute to small-town America of previous centuries. Victorian architecture dominates the streets. Many of the homes have become shops, primarily selling antiques and collectibles.

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