10 Coolest Small Towns, Hawaii

Waitsburg, Wash. Population: 1,212 Nearest City: Walla Walla, 21 miles Ross Stevenson and Leroy Cunningham settled in Waits­burg six years ago, in search of a quieter lifestyle. With two partners, they opened the Whoopemup Hollow Café in 2005. The Whoop, as it's known, dishes up jambalaya and Coca-Cola cake to wheat farmers and wine snobs alike (120 Main St., 509/337-9000, jambalaya $19). Just across the street, Jim German recently opened Jimgermanbar, which specializes in classic cocktails and small plates (119 Main St., 509/337-6001). His wife, Claire Johnston-German, owns the AMO Art gallery next door (117 Main St., 509/876-1264, amo-art.com). Summers in Waitsburg can get hot, and the Laht Neppur Brewing Co. is the place to cool down (444 Preston Ave., 509/337-6261). After savoring a flight of eight mini pours, head over to the Monteillet Fromagerie, where the cheeses are made with milk from free-range goats and sheep (109 Ward Rd., 509/382-1917). Monteillet's sheep's-milk gelato is a revelation.

Yachats, Ore. Population: 617 Nearest City: Eugene, 86 miles In 2005, Dave Thomas and Deb Gisetto left Vermont for Oregon and soon found themselves awestruck by the scenery around Yachats (yah-hots). "It was just unbelievably beautiful," recalls Thomas. "And the people were possibly the most friendly in the country." Thomas and Gisetto put down roots by opening Green Salmon Bakery & Coffee House (220 Hwy. 101, 541/547-3077). Yachats also has cute shops, like Raindogs (162 Beach St., 541/547-3000, raindogsonline.com), and a deli called Grand Occasions where you can watch the sea roll in while you eat pie made with blackberries, strawberries, or whatever's in season (84 Beach St., 541/547-4409). After staying in a Shamrock Lodgettes beachfront cabin, you may move to Oregon, too (105 Hwy. 101, 800/845-5028, shamrocklodgettes.com, cabins from $99).

Milford, Pa. Population: 1,292 Nearest City: New York, 71 miles A resort town since the Gilded Age, Milford is popular with newcomers interested in its Victorian houses. Sean Strub (a direct-mail and publishing entrepreneur who moved here in 1997) and retired executive Richard Snyder spearheaded the town beautification effort, launched Milford Magazine, and in 2001 bought the 1880s-era Hotel Fauchère. Five years and $6.5 million later, it reopened with heated slate bathroom floors, Frette sheets, and a price point that's ritzy for such a small town, not to mention Budget Travel (401 Broad St., 570/409-1212, hotelfauchere.com, from $275). The 70,000-acre Delaware Water Gap National Recreation Area is nearby (nps.gov/dewa); buy picnic supplies at Fretta's (223 Broad St., 570/296-7863). Kitchen and bath designer Derek Roberts moved to Milford in 1991. "My mountain bike is well used," he says. "After work, I like to go swimming in a waterfall." He has become such a civic booster that he began organizing Fluviarchy dance parties--named for the network of waterfalls--at The Emerson House (call the Fauchère for info). "Find me for free-drink tickets," he says.

Millerton, N.Y. Population: 925 Nearest City: New York, 103 miles There's no such thing as a straightforward stroll down Millerton's Main Street, even if it is only a couple of blocks long. Inevitably, you're tempted to pop into one shop, zigzag over to another, or grab a latte and a scone at Irving Farm Coffee House, an offshoot of a Manhattan café (44 Main St., 518/789-6540, irvingfarm.com). The Dutchess County village lies within 30 minutes of prime second-home destinations, yet Millerton has remained affordable and unpretentious. "This town feels very real," says Susan Schneider, who moved her business, Shandell's, which sells vintage and new lamps, from Connecticut to Millerton in 2004 (34 Main St., 518/789-6603, shandells.com). In 2005, Robin Helfand, a former manager of New York City's Dean & Deluca, opened a specialty food store, Millerton Market (21 Main St., 518/789-6677), and this past spring she launched another enterprise, Millerton Card & Candy Co. (28 Main St., 518/789-8669). Helfand credits Millerton's growing appeal to its old-fashioned Main Street: "It's full of independent businesses instead of chain stores," she says, "so you see products that reflect what the community really wants."