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Looking for a fun fall getaway? There's not much better than time spent in Stockbridge, MA during Autumn. Whether your perfect day involves fall festivals, shopping in one-of-a-kind boutiques, getting outdoors in all that nature has to offer, experiencing history and art, Stockbridge is guaranteed to please. Come & Stay in our quintessential New England town! Plan a weekend escape or an extended getaway to see the Autumn Leaf Show. Start your visit at StockbridgeChamber.org. | |
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Can't Miss Fall Activities
The Berkshire Botanical Garden's Harvest Festival in Stockbridge, MA is Oct. 12-13. The Harvest Festival has earned a reputation for being a quintessential Berkshire family event celebrating the autumn harvest when the 24-acre Garden is transformed into a vibrant hub featuring family fun and 50+ regional artisan food and craft vendors. The festival features live music performances, a giant tag and plant sale.
The Incredible Naumkeag Pumpkin Show is BACK from September 27 through October! This year with more pumpkins, more fun, and an expanded schedule! It's a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds. Hot cider and fall treats will be available for sale on-site. Advanced purchase of timed tickets is required and suggested as it does sell out fast.
For those seeking Ghost Tours, the Mount and Ventfort Hall Mansion and Gilded Age Museum, both in Lenox, MA offer tours through their historic estates sharing tales of their hauntings. Stand in the places where the eerie encounters occurred, listen to the first-hand accounts of those who experienced them, and maybe even experience something unusual yourself.
Another family fun activity is the tradition of apple and pumpkin picking at Windy Hill Farm located just a few miles south of Main Street, Stockbridge. Since establishing their farm in 1980, they typically have over 25 varieties of apples, including several heirlooms as well as their own fresh-pressed, all-natural unpasteurized sweet cider blend.
In addition to the can’t miss fall activities, there’s always live performances and exhibitions to view. From Folk-pop musician Suzanne Vega on October 5 and Pink Martini on October 12 at Mahaiwe Performing Arts Center in Great Barrington, MA to tributes bands like Van Morrison on October 18 and Bon Jovi and Journey on October 19 at the Colonial Theatre in Pittsfield, MA. The Stockbridge Library presents Honor and Hope: Two Mohican Artists, works of Terri OConnor and Rebecca Burr in their October art exhibit. The exhibit is open to the public during regular library hours from October 1 to 31. Portraits of extraordinary women go on exhibit November 9 at the Norman Rockwell Museum. Anita Kunz: Original Sisters, Portraits of Tenacity and Courage, presents selections from the artist’s groundbreaking series of portraits of diverse and extraordinary women from ancient times to today, many unknown or underrecognized. This exhibition uncovers, amplifies, and celebrates the achievements of changemaking women worldwide, while also weaving together a “lost history” of women’s distinctive contributions within every possible field of endeavor.
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Where to Dine
Alice’s Restaurant is no longer with us, but you can still get nearly anything you might want when dining out in the Stockbridge area. Whether your preference is an intimate café, a casual family-friendly restaurant, an old-fashioned lunch counter, or an historic inn, you’ll find it here. Part of the pleasure of being outdoors in Stockbridge includes its atmosphere for dining al fresco, many of which offer pet-friendly patios. High Lawn Farm in Lee, MA has been in continuous operations since the 1900s. It's a historic landmark fun for all ages. Enjoy a farm-fresh ice cream cone or artisanal cheese board at one of their picnic tables as their Jersey girls roam in the fields behind the shop. Then have a walk around the idyllic property, see where they milk their herd, and enjoy some of the best views in the Berkshires. At their on-site farm store, the Farmstead Creamery, they offer artisanal dairy products as well as a variety of other locally produced goods.
Where to Shop
As you travel in the Berkshires of Western Massachusetts viewing the spectacular autumn scenery, you will find fine art & craft galleries lining our main streets and back country roads. Some are open to the public by appointment only, while others welcome walk-ins. From upscale clothing to vintage finds to locally made gifts, specialty foods & wine, original art to home furnishing this area offers something of interest to everyone. In West Stockbridge, MA, Joel Hotchkiss has been designing and creating hanging mobiles for private and commercial installations since 1981 at Hotchkiss Mobiles Gallery. His hanging mobiles are currently owned and enjoyed by "mobile enthusiasts" throughout the United States, Europe and Canada and are sold in prestigious Museum Stores such as the GUGGENHEIM NYC, THE NATIONAL GALLERY in DC, THE ART INSTITUTE IN CHICAGO, SF MOMA as well as select galleries nationwide. Joel can be found most days in his studio crafting when you stop by the gallery to shop.
Where to Stay
Our New England Inns, B&Bs and Hotels are offering getaways complete with fires to lounge by, heated pools or saunas, afternoon teas, and scenic views. All properties are close to downtown Stockbridge where you can shop and dine. Get an overview of the properties in our area, go directly to their websites for the full picture, then book directly with the property of your choice. The Inn at Stockbridge is a six-acre Berkshires retreat, now revitalized into a modern bed and breakfast experience. Choose from spacious suites in the Main House to the cozy Cottage quarters while unwinding over delicious hot breakfasts or peaceful strolls around the grounds. This year they introduced a newly opened Bar & Lounge with entertainment on weekends.
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Hiking is an ever-popular autumn activity, and the variety of beautiful destinations for hiking in the Berkshires is plentiful. Within walking distance of downtown Stockbridge, located at the end of Park Street are three Laurel Hill Association Stockbridge trails. Founded in 1853, The Laurel Hill Association is the nation’s oldest village improvement society. They maintain over 460 acres of properties in Stockbridge for the public to enjoy. Download maps for Mary Flynn, Laura’s Tower, and Ice Glen Trails.
Ice Glen Trail: A climber over, under and around giant boulders in a glacial ravine 1-mile round trip. The sides of the glen are covered with old stand pine and hemlock. At the south end of the glen is reputedly the tallest pine in Massachusetts.
Laura’s Tower Trail: A quiet 1.5 mile round trip, wooded assent, starting out through old stand pine and hemlock. Nearing the end of the climb is a large section of birch interspersed with mountain laurel. A metal tower at the summit provides a panoramic view of the middle Berkshires. On a clear day, one can see 68 miles west to the New York Catskills, and 50 miles north to the Green Mountains in southern Vermont.
Mary V. Flynn Trail: An easy 1.2 mile round-trip walk in the woods and along the Housatonic River, on a wide, packed-gravel trail, built mostly on the bed of the old Berkshire Street Railway trolley line. Those looking for a family-friendly picnic can also visit Bidwell Park nearby. There, picnic tables, playground equipment, and tennis courts await.
Outdoor Gardens & Art Walks: Discover the beautiful gardens, grounds, and scenic views in our area. Most of our gardens, museums and historic sites are open for use of their outdoor grounds and sculpture parks with restrictions. Check out each venue’s website for their offerings.
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Autumn offerings: click on image for details | |
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