Leafing Town

Those who prefer to hibernate in the A/C until the heat and humidity have become a fading memory—or who simply have vacation days to burn off before year’s end—would do well to consider heading north to western New England, where the crisp autumn air and colorful leaves of the Berkshires quietly beckon.

Just a couple hours’ drive from Westchester (and a toll-free one at that), the Berkshires and its northern neighbors, Vermont’s eponymous Green Mountains, offer some of the region’s best venues to experience the fall’s foliage in all its radiant splendor.

As a rule of thumb, the farther north and the higher in elevation you go, the earlier the leaves change color. The weather is also a vital catalyst: cooler temperatures will hasten the change, while an “Indian summer” or more temperate weather will often delay the onset of Mother Nature’s much-anticipated technicolor show. And the amount of precipitation impacts the leaves’ vibrancy: a dry spring or summer usually will result in muted colors and leaves dropping earlier. Ideal foliage follows a warm and wet spring, typical summer conditions, and mild, sunny autumn days with cool (but above-freezing) evenings.

When to go: In a typical year, the fall foliage peaks in the Green Mountains and the Berkshires in early October, making Columbus Day weekend a popular time to go—so booking accommodations in advance is essential. However, the colors often will peak later or at least remain vibrant through much of the month. For up-to-the-minute reports on foliage conditions, check the following websites, updated regularly by professional leaf-peeping scouts: for Massachusetts (massvacation.com/scienceNature/fall-foliage.php) and for Vermont (vtonly.com/foliage.htm).

Getting there: Take the Taconic Parkway north to the Hillsdale exit (Route 23 East). Proceed on Route 23 East into Massachusetts. Route 23 East will lead you to Main Street in Great Barrington, the hub of the southern Berkshires. From Great Barrington, you can proceed north on U.S. Route 7, which serves as the main thoroughfare in the Berkshires and Green Mountains—running north-south from Canada to Connecticut, most of the region’s quaint villages and charming towns are dotted along its corridor.

DRIVING TIMES: Berkshires (2-3 hrs), Green Mountains (4-5 hrs).

Southern Berkshires

Where to Stay: While both chain motels and bed and breakfasts abound, Days Inn (Great Barrington; 413-528-3150) is the only accommodation situated directly upon the town’s Main Street/downtown area. For the quintessential New England inn experience, nothing quite compares to the Red Lion Inn (413-298-5545; red lioninn.com), a storied landmark open since the 18th century. If staying there feels like you’ve walked into a Norman Rockwell painting, it’s because you have—Rockwell featured the Inn and the adjacent shops in his famous Stockbridge Main Street Christmas.

Dining Suggestions: Cute, artsy Martins in Great Barrington (413-528-5455) serves up homestyle breakfasts (including homemade granola) all day long. 20 Railroad Street in Great Barrington (413-528-9345) delivers dependable pub fare with a health-conscious twist. Chef-owned Cork ’N Hearth in Lee (413-243-0535; corknhearth.com) offers fine New England dining in a rustic setting overlooking Laurel Lake.

Treats: SoCo Creamery in Great Barrington (413-528-9420; sococreamery.com) serves homemade ice cream with seasonal flavors (like October’s pumpkin) from a local microcreamery. Catherine’s Chocolates (Great Barrington; 800-345-2462; catherineschocolates.net) is a fourth-generation, family-owned confectionery celebrating 50 years of crafting handmade candy.

Scenic Drives: Route 183, from Great Barrington to Lenox; Route 8, from Otis to Pittsfield; Route 23, from Great Barrington to Otis.

Scenic Walks: The “Pond Loop” circumscribing Benedict Pond in Beartown State Forest in Monterey (mass.gov/dcr/parks/western/bear.htm), just east of Great Barrington, is a pleasant, level, hourlong trail. For those seeking more ambitious walks and vistas, spend an hour-plus hiking to the top of Monument Mountain in Great Barrington (thetrustees.org/pages/325_monument_mountain.cfm), the highest peak in the south county. Two trails (“easy” and “difficult”) lead to the summit, where area resident Herman Melville and his pals Nathaniel Hawthorne and William Cullen Bryant found inspiration for their writings.

Shopping Stops: The southern half of the Berkshires is an antiquing mecca (especially Sheffield), with innumerable shops up and down Route 7. In addition, the main streets of Great Barrington, Stockbridge, West Stockbridge, Lee, and Lenox all offer an array of cute, charming, non-chain stores, eateries, and galleries. For more hardcore shopping, check out The Berkshire Outlet Village in Lee (413-243-8186).

Photo Ops: Heading north on Route 183 towards Lenox, turn left on Richmond Mountain Road. About a mile up on the left is Olivia’s Overlook, which overlooks Stockbridge Bowl.

Rainy Day Plan B: The Norman Rockwell Museum in Stockbridge (413-298-4100; nrm.org) showcases the world’s largest collection of the artist’s work. Rockwell lived much of his life in the Berkshires, and his studio—preserved down to the last brush since his death—is located on the museum’s grounds. The area also features several glass galleries, including Holsten Galleries in Stockbridge (413-298-3044; holstengalleries.com), which presents the stunning glass sculptures of Dale Chihuly.

Photo by Lee Krohn, 2008 The October sun illuminates the foliage blanketing Vermont’s Mount Equinox.

Photo by Lee Krohn, 2008

Northern Berkshires

Where to Stay: Travelers seeking avant-garde accommodations should check out The Porches Inn in North Adams (231 River St; 413-664-0400; porches.com). These artistically renovated row houses mix modern and retro décor. Those who prefer more traditional New England lodging would feel at home at The Williams Inn (413-458-9371; williamsinn.com). Set amid the stunning campus of Williams College, the Inn is within walking distance of Williamstown’s main street. Those wanting to “rough it” a bit can bunk at Bascom Lodge. Perched on the summit of Mount Greylock, the lodge offers dorm-style accommodations and family-style meals.

Dining Suggestions: Steak and seafood lovers should try locals’ favorite Dakota in Pittsfield (413-499-7900), a warm, wood-paneled restaurant with a fireplace resembling a mountain lodge. Their über-popular salad bar is sourced mostly from Berkshire farms. Mill on the Floss in New Ashford (413-458-9123; millonthefloss.com) presents French country cuisine in a charming 18th-century farmhouse with an open kitchen. Jae’s Inn in North Adams (413-664-0100) serves fine pan-Asian cuisine in a pastoral setting.

Treats: The Store at Five Corners in Williamstown (413-458-3176; 5-corners.com) is the nation’s oldest continuously operating general store. While browsing its well-edited selection of wines, souvenirs, and gourmet groceries, be sure to sample its array of homemade baked goods and creamy fudge du jour.

Scenic Drives: Motor to the top of Mount Greylock, the highest peak in Massachusetts, for a breathtaking view of five states (especially if you’re ambitious enough to climb to the top of the 92-foot granite Memorial Tower). Route 7, from Lanesboro to Williamstown, offers some amazing vistas. Route 2, aka The Mohawk Trail, is the country’s first designated scenic highway. You can pick up this east-west route in Williamstown. Be sure to time your drive with the sun at your back (i.e., morning for westbound, afternoon for eastbound), so the foliage in front of you is well lighted.

Scenic Walks: For a very different walking experience, try a Berkshire Mountain llama hike. Originating from Hawkmeadow Farm
in Lee (413-243-2224; hawkmeadowllamas.com) each hiker is paired with a docile, affectionate llama (they’re known to steal kisses!) for a picturesque walk through neighboring October Mountain State Forest.

Shopping Stops: Berkshire Fine Hand­crafts
in Pittsfield (413-236-6969; berkshirefine handcrafts.com) sells creations from more than 130 area artisans, plus a variety of fair trade imports. The Berkshire Open Market (Lenox; 413-443-0025; berkshireopenmarket.com) features dozens of local vendors. Open Saturdays year-round at the Aspinwall Village, rain or shine.

Photo Ops: Jiminy Peak ski resort in Hancock (413-738-5500; jiminypeak.com) offers autumn chairlift rides for spectacular leaf peeping from its summit on the weekends.

Rainy Day Plan B: The Clark Art Institute
in Williamstown (413-458-2303; clarkart.edu) boasts one of the region’s best collections of Impressionist, American, and Old Master paintings. Housed in a 19th-century factory, MASS MoCA (North Adams; 413-662-2111; massmoca.org) has become the country’s largest center for contemporary visual arts, offering more than you could possibly see.

Southern Vermont

Where to Stay: Recently completing a multi-million dollar renovation, The Equinox Resort & Spa in Manchester Village (800-270-2132; equinoxresort.com) delivers a full-service, pampered experience in rooms and suites spanning four buildings—and pets are welcome, too. For inn-like ambiance on a motel budget, check out The Bennington Motor Inn (802-442-5479; coolcruisers.net). Situated on a hillside, the Inn is just three blocks from downtown Bennington.

Dining Suggestions: Tally’s at the Historic Bennington Station in Bennington (802-442-4700), an 1898 train depot-turned-tavern, is a reliable choice for lunch or dinner. Up For Breakfast in Manchester Center (802-362-4204) is a cozy, all-breakfast café on the second floor, overlooking Main Street. Quirky Alldays & Onions in Bennington (802-447-0043; alldaysandonions.com) serves breakfast, lunch, and dinner daily, with a varied menu featuring locally sourced foods and an in-house bakery.

Treats: Load up on your quota of Vermont maple syrup, apples, cheddar cheese, and baked goods at The Apple Barn (Bennington; 888-8APPLES; theapplebarn.com). Be sure to try the juicy, hybrid Honeycrisp apples, which enjoy a short but popular season in October.

Scenic Drives: Make your way up Skyline Drive on Mount Equinox, where plenty of picnic and parking areas offer picturesque grazing and gazing spots. The Molly Stark Scenic Byway, aka Route 9, crisscrosses Vermont from the New York State line to the west, to the New Hampshire State line to the east.

SCENIC WALKS: The Healing Springs Nature Trail encircles Lake Shaftsbury in Shaftsbury State Park, Shaftsbury.

Shopping Stops: Manchester Center is an interesting hybrid of quaint New England town and outlet store village. Indeed, the two are so intertwined it’s often hard to tell where one ends and the other begins. Those seeking one-stop shopping should visit the Shops at Camelot Village in Bennington (shopsat
camelotvillage.com). Nestled in 18th-century barns, the village offers an antique center, a crafts center, a country store, a winery, flowers, Yankee Candles, and vintage clothing.

Photo Ops: A quick elevator ride to the top of the Bennington Battle Monument in Bennington offers a four-sided view of three states. Just up the road from the monument is Old First Church, in whose graveyard resident Robert Frost is buried.

Rainy Day Plan B: Bennington boasts five covered bridges along its back roads. Pick up a map and tool around the pastoral countryside in search of these historic structures.

Northern Vermont

Where to Stay: The Black Bear Inn in Bolton Valley (802-434-2126; blkbearinn.com) provides a romantic respite for travelers. This mountaintop inn offers incredible views, and myriad hiking, biking, and horseback riding trails throughout its massive acreage. The elegant Willard Street Inn in Burlington (802-651-8710;willardstreetinn.com) features just 16 guestrooms, a solarium with a view of Lake Champlain and an English Garden. The family-owned Countryside Motel in Shelburne (802-985-2839; countrysidevt.com) is located amid many of the area’s major tourist attractions and is a quieter alternative to staying in downtown Burlington.

Dining Suggestions: Burlington’s Penny Cluse Café (802-651-8834; pennycluse.com) draws hordes of locals and tourists alike for its varied breakfast fare. Be sure to try its gingerbread pancakes. Named after one of area resident Robert Frost’s poems, Fire & Ice in Middlebury (802-388-7166; fireand icerestaurant.com) offers an impressive range of lunch and dinner options (including a popular salad bar) set amid a museum-like atmosphere of antiques. Feeling carnivorous? Try Souza’s in Burlington (802-864-2433), an authentic Brazilian churrascaria (barbecue).

Treats: Lake Champlain Chocolates in Burlington (802-864-1807) offers hourly tours of their facility (and samples of their yummy handiwork).

Scenic Drives: Route 125, aka The Middlebury Gap Road, from Ripton to Hancock; Route 108 from Cambridge to Enosburg Falls; Route 105 from Enosburg Falls to St. Albans; Route 78 from Swanton to Route 2, which will wend you onto and through the islands in Lake Champlain and back onto the mainland.

Scenic Walks: The Trail Around Middlebury, or TAM, is a 16-mile footpath encircling the village of Middlebury. The Robert Frost Interpretive Trail, also in Middlebury, celebrates the works of Vermont’s poet laureate. Excerpts of Frost’s poems are posted throughout the trail, which spans several boardwalks and bridges.

Scenic Cruises: The Spirit of Ethan Allen in Burlington (802-862-8300; soea.com) provides a 90-minute narrated lunch cruise around Lake Champlain daily.

Shopping Stops: Church Street Marketplace (churchstmarketplace.com) is a brick-lined, pedestrian-only shopping arcade running through the heart of downtown Burlington, often featuring live entertainment and special events. A free bus service shuttles pedestrians between Church Street and Burlington’s sprawling waterfront. Pick it up at the corner of Church and College streets.

Photo Ops: Smuggler’s Notch, a breathtaking mountain pass in Mount Mansfield State Forest, east of Burlington, offers several spots to park and snap away at the scenery below.

Rainy Day Plan B: Head to the Ben & Jerry’s Factory in Waterbury (866-BJ-TOURS; benjerry.com). After taking a tour of their plant (and learning just how many quarts of Chunky Monkey employees can take home free each month), sample some for yourself. Be sure to visit the Flavor Graveyard outside, and pay your respects to all the favors that have come and gone through the years.