Rocheport, Missouri

Great Barrington looks like the small town of Norman Rockwell's dreams--especially on Saturday mornings in summer, when folks turn out to watch free outdoor kids' concerts that take place in a gazebo. In the southwest corner of the state, Great Barrington is the kind of comfortably supportive place that inspires locals to try new things. Last summer, native Daniel Mazursky pushed himself out of his comfort zone to open the SoCo Creamery, a gourmet ice cream shop that now has a second location in Lenox and supplies restaurants across the region (5 Railroad St., 413/528-9420, single cone $3). Michigan native Matthew Rubiner, meanwhile, was a researcher at M.I.T. before learning how to be a cheesemonger. His eponymous shop is in an 1869 building that used to be a bank; Rubiner recently finished converting the old vault into a cheese-ripening room (264 Main St., 413/528-0488). Creative reuse is common: In 2004, artist Marilyn Kalish transformed the vault of the former Mahaiwe Bank into an exhibition space for the Vault Gallery (322 Main St., 413/644-0221), and Jane and Sam Kasten established SKH Gallery in what used to be Great Barrington's train station (46 Castle St., 413/528-3300). Perhaps the best example of residents' can-do attitude is the River Walk. Since 1988, more than 2,000 volunteers have cleared 375 tons of debris from the banks of the Housatonic River, which runs through town. In 1992, the first section of trail was unveiled--all 136 feet of it. The Walk now covers about half a mile, and it's growing. Rachel Fletcher, the founder of the project, came to Great Barrington in 1981 and never left. "The spirit of community kept me here," she says. "You can really get involved without having to write a check. Everyone here--from old-timers to new arrivals--really takes care of the town."

Hudson has come a long way in the last 200 years. The 19th century saw it go from thriving port to mob-run den of mayhem. Drawn in part by the colonial architecture that somehow survived the town's ups and downs, Manhattan designers rediscovered Hudson in the early 1990s as an antiquers' paradise. Today, it's entering its third act. A new community of urbanites is making the two-hour trip up from New York City, downsizing, and living out their low-key fantasies. Take Leong Ong, a fashion designer whose women's clothing is sold at Barneys, Henry Lehr, and Fred Segal; two years ago, he chose Hudson for his only stand-alone store (409 Warren St., 845/687-7516). "It's eclectic, with lots of artists and writers," explains Michael Albin, a former English professor who moved here in 2004 with his wife, Marianne Courville, and their daughter, Beatrix. The erstwhile Brooklynites filled a niche with their shop, Hudson Wine Merchants. A corner is cordoned off as a play area for Beatrix; the family lives on the second floor; and the top floor houses a photography gallery that's curated by Courville (3411D2 Warren St., 518/828-6411). Jeff Gimmel and his wife, Nina Bachinsky Gimmel, also decamped from New York. "We were burnt out on the city," explains Jeff, who had been executive chef at power-lunch spot Michael's; Nina worked in the pastry kitchens at Union Square Café and Le Bernardin. In 2004, the couple started their own business: Swoon Kitchenbar, which features food from local farms and flowers picked by Nina's mom (340 Warren St., 518/822-8938, butternut squash risotto $18). "Five minutes away, you're in farmland," Jeff says. "Yet in town, it feels like lower Manhattan--you can see art, get a nice bottle of wine, and still do Pilates." Kelley Drahushuk is a native Hudsonite who left and moved back. Last summer, she and her husband, Alan Coon, opened The Spotty Dog Books & Ale in a former firehouse. Browsers linger over glasses of wine and pints of Evans' Ale, which is brewed by Drahushuk's uncle, at a bar made from wood that used be a lane in a bowling alley (440 Warren St., 518/671-6006). Drahushuk never imagined she'd return. "There was no café!" she says. "There was no cute lunch spot!" But she couldn't resist the eternal lure of cheap real estate: "I've always wanted to have a little store of my own, and we could do that here."

On a plateau above New River Gorge National River park, Fayetteville is an adult's all-natural playground. In the last decade, a wave of adrenaline junkies has come to the southern West Virginia town for work (mostly as river rafting guides) and opted to stay for good. "There aren't many towns in the U.S. where you can walk out your front door and recreate in so many ways," says Kenny Parker, a transplant from nearby Blacksburg, Va. "There's world-class white-water rafting, some of the best rock climbing around, and excellent mountain biking." Parker and fellow rock climber Gene Kistler co-own Water Stone Outdoors, an outfitter that specializes in climbing gear (101 E. Wiseman Ave., 304/574-2425). Sharon Rynard also divides her time between the outdoors and her indoor business. A painter and printmaker from Indianapolis, Rynard moved to Fayetteville 10 years ago to be a river guide. These days, she's also a climbing guide, ski patroller, and owner of Studio B Gallery & Gifts (101 S. Court St., 304/574-9100). "Why would anyone stick with just one thing in a place where there's so much to do?" she asks. Fayetteville's nerve center is Cathedral Café (134 S. Court St., 304/574-0202). A deconsecrated Methodist church--stained-glass windows and all--it's where locals meet to sip coffee, catch up on river reports, and check e-mail. The restaurant is owned by Wendy Bayes and her husband, Rick, who met in Fayetteville as river guides nearly 15 years ago and thought running a café would be a good way to put down roots after their daughter was born. Bayes hasn't given up her thirst for adventure, though. She still makes time to go out on the river and hike nearby trails: "You never have to grow up. It's like Neverland."

Once a rowdy copper mining town, Bisbee--in the Mule Mountain range, 90 miles southeast of Tucson--still attracts a fair share of misfits and folks on the fringe. "Bisbee is for people who don't like the ordinary," says longtime resident Cynthia Conroy, a dog trainer. One prime example is Reed Booth, a.k.a. the Killer Bee Guy. Booth removes swarms of killer bees from wherever he finds them, collects their honey, and sells it at his downtown store, Killer Bee Honey (15 Main St., 520/432-2938, eight-ounce jar $6). Then there's Greg--no last name--who has trained his pets to stand in a pyramid: bird atop cat atop dog. (Sometimes, there's a mouse, too.) Greg can regularly be seen parading his menagerie around. Stylish amenities are slowly joining Bisbee's oddities. On the first Monday night of each month, the Prickly Pear Cafe has a themed meal and movie night. To accompany the 1998 film Run Lola Run, they served bratwurst and sauerkraut (105 Main St., 520/432-7337, movie night dinner $8). Behind the café is the Old Bisbee Wine Merchant; both are co-owned by partners Ryan White and O'Neil McGean. "We came for a visit and fell in love with Bisbee," says White. And at the Shady Dell, nine restored 1950s trailers, a yacht, and an old bus constitute the town's hippest motel (1 Douglas Rd., 520/432-3567, theshadydell.com, from $45). Since Bisbee sits in a narrow gap in the mountains, staircases often double as streets. To fully understand what makes the place so special, Conroy suggests standing at the top of the stairs and just . . . listening. "Normal sounds take on a musical tone," she says.