Steeple chase: A scene from the town.

BY TARA MANDY

Nestled among small new england towns like Lenox and Norman Rockwell's Stockbridge, Great Barrington has been a summer retreat for sophisticated New Yorkers since the nineteenth century, when Nathaniel Hawthorne, Henry David Thoreau, Edith Wharton, and Herman Melville kick-started its evolution from mill town to arts-and-culture epicenter. But Great Barrington is still a rural town, and the most coveted second homes are often tucked away on dirt roads. "We love that we can dress down in jeans and sneakers yet still get our fill of Manhattan-worthy arts," says one weekending couple. "Some of the galleries -- and many of the restaurants -- are as good as those in the city," says another. "But minus the attitude."

The Great Outdoors: Active types hike the two-mile loop around Benedict Pond in Beartown State Forest or head just a few miles north to Monument Mountain, where a 2.6-mile climb to the summit brings you to an idyllic picnic spot with spectacular views. There's also excellent fly-fishing (Green River and Williams River are hot spots for trout and small-mouth bass), horseback riding, and boating. Benedict Pond and the Housatonic River draw canoe and kayak enthusiasts.

Artists' Colony: Hot tickets include Tanglewood, where the Boston Symphony Orchestra plays every weekend in July and August, and Jacob's Pillow, New England's most popular modern-dance festival. "There's also the Norman Rockwell Museum and great antiquing along Route 7 between Great Barrington and the Connecticut border," says one Fifth Avenue resident who's had a second home in Great Barrington for almost ten years. And there is a slew of local galleries to explore, including the Loring gallery, Joyous Spring Pottery, and Holsten Galleries, known for its large selection of Chihuly blown glass.

Summer Gossip: "Seiji Ozawa's retirement announcement was all anyone talked about last year," groans one second-home owner. "People were actually placing bets on who was going to take over the BSO!" Now that the baton has been passed to James Levine, vacationers are gossiping about who got tickets to the farewell performance and who was shut out. "It's such a touchy subject," says one lucky attendee.

What's New: Bizen, the always-packed Japanese restaurant on Railroad Street, is expanding into the space next door and will showcase owner Michael Marcus's pricey handmade pottery as well as a traditional Japanese tea ceremony. The Mahaiwe Theatre, a movie theater built in 1905, is being renovated and will house the Berkshire Opera Company. Although funding has been slow, and the company is staging only one major production this year (The Turn of the Screw), residents still think "it's going to do wonders for the town's cultural quota." Talk about an embarrassment of riches.

Property Values: Summer rentals are available in Great Barrington (ranging from $2,500 to $30,000 per month), but second homes are more common. You'll find an equal number of Victorian homes, lakeside cottages, and farmhouses; the most expensive are secluded, with large acreage and mountain views or proximity to a lake or pond. "The main draw is Tanglewood," says Dorian Held, who has been selling vacation homes to New Yorkers for almost twenty years. "Everyone wants to be within a fifteen-minute drive." Recent sales include a four-bedroom Victorian a short walk from town for $557,500; a three-bedroom contemporary with a pool on a quiet country road for $570,000; and an 1850s farm house with six bedrooms on 33 acres for $660,000.

Recommended Realtors: Dorian Held at Wheeler & Taylor Realty (413-528-1006), Apple Hill Realty (413-528-3458).

Weekend Visits: Stay at the Wainwright Inn, a modest bed-and-breakfast in a converted Victorian within walking distance of downtown (413-528-2062 or wainwrightinn.com; rooms start at $150). Book a table well in advance at Aegean Breeze, a new Greek restaurant that serves delectably fresh charcoal-grilled whole fish (413-528-4001).