St. Michaels, Maryland
During the War of 1812, St. Michaels earned the nickname “The Town That Fooled the British.” The ruse was simple: When locals got word that a nighttime bombardment was coming their way, they hung lanterns in treetops and atop ships’ masts, so that the enemy gunners on Chesapeake Bay overshot all but one of the houses in the village.

St. Michaels was also overshot—and overlooked—by the march of progress along the bayfront. The town lies on Maryland’s Eastern Shore, southeast of Annapolis, and until the 1952 opening of the Chesapeake Bay Bridge, most of its neighboring communities were backwaters given over largely to shipbuilding, tobacco farming, and harvesting what H.L. Mencken called an “immense protein factory” of crab and oysters. Even now, though shellfish stocks in the bay have been substantially depleted, you can pass through St. Michaels to the end of the peninsula and watch watermen leaving to harvest oysters on their wooden skipjacks, the last sailing vessels still in regular commercial use in the United States.

The Bay Bridge brought regional development, but St. Michaels occupied such a narrow slip of land that the town has never had much room to expand. It’s also benefited from long-standing local taste for historic preservation. The compact village center boasts a wealth of 18th- and 19th-century structures, including the one house struck by a British cannonball. The historic district is anchored by the renowned Chesapeake Bay Maritime Museum, which features a collection of 85 vessels that trace the evolution of regional boatbuilding. The museum’s Hooper Strait Lighthouse, moved here from Tangier Sound farther south, has become as much a symbol of St. Michaels as the mountains of steamed crab served on the deck at The Crab Claw Restaurant.

St. Michaels is a town for walkers and cyclists, where nothing is far from anything else. Heading out of the village can mean an excursion on some of the best sailing waters in the nation (there are a couple of downtown marinas and a local yacht club), a drive 35 miles south to view eagles and ospreys on the 27,000-acre Blackwater National Wildlife Refuge, or a trip across the Delmarva Peninsula to the Atlantic. Annapolis, Baltimore, and Washington, D.C., are just a few hours away via the Bay Bridge.

what the locals know
Museums are often regarded primarily as attractions for visitors, but it’s become a regular ritual for many St. Michaels residents to head down to the grounds of the Chesapeake Bay Maritime Museum and enjoy spectacular sunsets over the water.

Population: 1,139
Median Home Price: $795,000
For More Info: stmichaelsmd.org

Port Townsend, Washington
The standard take on the Pacific Northwest is that it rains an awful lot. But Port Townsend, located on the tip of the Quimper Peninsula just south of the San Juan Islands, enjoys a sunny microclimate. Protected from prevailing weather patterns by the Olympic Mountains, it averages less than 20 inches of rain a year, and often basks under clear skies while towns like Port Angeles to the west keep umbrella makers in business.

Getting here requires some planning. If you start in Seattle you can take a 30-minute ferry ride to Bainbridge Island (bring a windbreaker so you can stand outside as you cross Puget Sound); travel another hour in the car to the Hood Canal Bridge. Then drive up the eastern side of the Olympic Peninsula to the edge of the Strait of Juan de Fuca. Think you’ll be tired when you arrive? Don’t worry—the stunning coastal scenery will revive you.

Like a village out of a musical, Port Townsend is a town that time forgot—only in this case, time suddenly remembered and brought it back to life. Historic mansions occupy some of the prime real estate here, and smaller Victorian houses painted vivid colors line the narrower streets. Many of the finest homes date to the late 1800s, when boosters promoted the town as a major rail terminus. Unfortunately, the Northern Pacific Railroad failed to cooperate, and the community all but disappeared.

Then, about 1970, urbanites looking for lovely surroundings and cheap real estate discovered Port Townsend. Here was a compact, walkable town with a picturesque waterfront far enough from Seattle to keep sprawl at bay.

The community they created was a match for the setting. Today it pulses with environmentally friendly businesses, art galleries, plenty of live theater, and festivals celebrating jazz, blues, and classical music.

Visit in September and you can catch the 31st Annual Wooden Boat Festival—“the Woodstock of wooden boats,” sponsored by the local Wooden Boat Foundation and Northwest Maritime Center. Both organizations occupy space on the town’s historic waterfront, where they educate students and visitors about the region’s sailing heritage and environment.

Sea kayakers often set off from their dock to ply Port Townsend Bay and Admiralty Inlet. And when they come home, they can stroll down to the brewpub—without their slickers.

what the locals know
Susan Grantham, who works with the Port Townsend Chamber of Commerce, likes to take in movies at the Victorian-era Rose Theater. “The Rose shows first-run pictures as well as independent and art films,” says Susan. “All movies begin with a live introduction by the staff, and the 20-plus toppings for the popcorn can’t be beat. Monday is ‘fabulous door prize night,’ so save your ticket stub for the drawings.”

Population: 8,900
Median Home Price: $399,000
For More Info: ptguide.com