The Berkshires Massachusetts
The Berkshires Massachusetts

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Fall Favorites

Wine As the green leaves of summer turn magenta and gold, harvest time in the Berkshires brings a celebratory, yet tranquil air to the region's stunning vistas, fascinating history and renowned arts. Fall is the time to explore those out-of-the-way, unspoiled small towns, drink fresh-pressed apple cider and join in the autumn festivities. The cooler weather also invites outdoor adventures such as hiking and biking.

To help you make the most of your vacation, we've compiled a list of ten favorite fall activities. Choose one or mix and match for a truly memorable Berkshires experience.

  1. Go antiquing. Put your hunting and gathering instincts to the test! You'll find hundreds of antiques shops along both Route 7, known as the "Antique Highway," and Route 20. Local dealers offer everything from 17th century English furniture to Asian sculpture to estate jewelry. You can even learn how to become an antiques dealer yourself through "Encore Berkshires!"

  2. Take a hike. Join in a Berkshires tradition by participating in the 38th Annual Mount Greylock Ramble. Every Columbus Day, hundreds of hikers ascend to the top of Mount Greylock, the state's highest peak, along the Cheshire Harbor Trail. The moderate hike is fun for all ages. This year's event will take place on October 13. Contact the Berkshire Chamber of Commerce for more information at 413-663-3735.

  3. Toast the season. Visit the family-run Land of Nod Winery in nearby Connecticut and take a leisurely walk through the picturesque vineyards. Afterwards, enjoy a special wine tasting. Call 860-824-5225 for information.

  4. Leaf peeping. Peak foliage time in the Berkshires is usually around the first week in October, so hop in the car for an unforgettable fall foliage experience. Travel north along Route 7 from Sheffield to Williamstown to see stunning vistas swathed in array of red and golden shades. Another popular (though sometimes crowded) drive is along Route 2 through the scenic Mohawk Trail.

  5. Follow the Mohawk Trail. This "Highway of History" began as a small Native American footpath nearly three hundred years ago. Today, the Mohawk Trail stretches along the Massachusetts/New York state line with more than 100 attractions along the way, offering excitement for the entire family. See the unique, beautiful Bridge of Flowers stretching across the Deerfield River; explore ancient glacial potholes at Salmon Falls; marvel at New England's only Natural Bridge; buy homemade wares at craft villages; watch a Native American Pow Wow; and much more. For more information on the Trail, call 413-743-8127.

  6. Celebrate. During the fall season, harvest festivals and old-fashioned fairs showcase the bounty of local farmers. Sample apple cider at the Bennington Museum's Apple and Harvest Festival, or see an animal parade at the County Fair and Crafts Festival in Hancock Shaker Village. The weeklong Fall Foliage Festival hosts numerous events, including the annual Fall Foliage Parade and a Phantom Leaf Hunt. The 17-day Big E is the ninth largest fair in North America. Celebrate the start of autumn at the 24th Annual Apple Squeeze Festival or venture back in time to the Gilded Age at the 12th Annual Tub Parade, both of which take place in Historic Lenox Village. And don't miss the Berkshires' longest running event: the Annual Harvest Festival. The fun takes place at the Berkshire Botanical Garden and includes rides, games, food and more.

  7. Shop 'til you drop. Bring home a one-of-a-kind decoration or objet d'art from one of the many unique galleries and boutiques throughout the Berkshires. Area artists experiment with a variety of unique media, and the galleries range from the artist-owned, single-focus gallery to large houses with international reputations that exhibit world-renowned masters of their craft. Art aficionados can also check out the gift shops at MASS MoCA, Norman Rockwell Museum and the Berkshire Museum. Pick up seasonal gifts at the Holiday Marketplace or get an original work of art at the Berkshire Art Festival.

  8. Go gourmet. Berkshire chefs excel at artful creations and will tempt you with a mouthwatering array of gastronomical delights. Cooks showcase their talents at area food festivals, including the Epicurean Tomato Fête and the Berkshire/Columbia Slow Food Festival. Another special treat is attending a Shaker Supper, in which you can enjoy dinner by candlelight at the Hancock Shaker Village.

  9. Bike the Berkshires. For those who prefer two wheels to four, journey through the Berkshire Hills along the Great Barrington Short Loop. This 11.1-mile ride begins just north of Great Barrington on Route 7 and goes uphill to Monument Mountain. It then loops back down Monument Valley Road to Route 23, past the Butternut Basin ski area and back into Great Barrington. Happy trails!

  10. Do it yourself. A scenic drive along a backcountry road will most likely lead to a farm where you and your family can pick your own apples or pumpkins. The apples are ripe and ready for the picking at Windy Hill Farms in Great Barrington and Mohawk Orchards in Shelburne. Find the perfect pumpkin at Ioka Valley Farm in Hancock or Whitney's Farm Stand in Becket.