Discover Massachusetts: The Berkshires All Year Long

by Matthew Wexler

EDGE Media Network Contributor

Monday July 27, 2015

Head to western Massachusetts for a Gilded Age dream any time of year. From rolling orchards and farm-to-table cuisine to an unparalleled cultural scene that draws global talent, the Berkshires is the perfect D.I.Y. getaway for romance, adventure, and a true sense of American spirit.

While gay marriage is now legal across the U.S., Massachusetts was at the forefront when it became the first state to allow same-sex marriage back in 2004. The LGBT community will find the Berkshires welcoming visitors with open arms whether it's for a blowout wedding, weekend getaway, or fun-filled day trip from Boston or New York City. Take a peek at our favorite picks and starting planning your vacation.

Last-Minute Summer Getaways: Pittsfield

Summer is high season in the Berkshires and with good reason. The region is packed with live performances of every variety and the restaurants overflow with seasonal ingredients. Be sure to check out:

  • From the theater that originated the Tony Award-winning "25th Annual Putnam County Spelling Bee" and this season's Broadway revival of "On the Town," Barrington Stage Company presents "His Girl Friday" (August 6-30), a new play adapted by John Guare based on the hit film of the same name that examines the cutthroat antics of the Chicago press world circa 1939.

  • Before or after the show, head to Pittsfield's newest restaurant, Methuselah Bar and Lounge. The quirky name references the oldest living man from Biblical scriptures and likely speaks to a well-fed life with cocktail in hand. Be sure to check out the craft cocktail menu, featuring intoxications such as the Heather in Queue, made with Ransom Old Tom barrel aged gin, Dolin Blanc vermouth, Pierre Ferrand dry curacao and Fernet Vittone. The menu offers twists on familiar favorites with some Mexican flair, including 'Pigs in a Blanket' made with Red Apple Butchers brats and Hosta Hill Crimson Kraut; and roasted butternut squash tacos.

  • Stay for the night at the newly opened Hotel on North. Two 19th century buildings were preserved, restored, and reimagined to create a unique footprint that honors the past while still including modern amenities. Each of the 45 rooms is different, some with working fireplaces, others with curated minibars featuring locally sourced items, and the pièce de résistance, the Library Suite, a majestic 644-square-foot corner suite featuring 125 bookshelves, clawfoot tub, and panoramic views... you may never want to leave.

  • Falling in Love

    As the nights get crisp and the leaves begin to change, there is no other more picturesque setting than the Berkshires. Head to the region in fall and discover the following:

  • Hilltop Orchards offers 200 acres to explore amid woodland trails designed by seven-time Olympic athlete John Morton. After a day in the field, enjoy a wine tasting at on-site Furnace Brook Winery, pick some apples from the orchard (which grows more than 26 varieties), or indulge in Hilltop's famous cider donuts.

  • Formed in 2005 as the Pittsfield Jazz Festival, the founders rebranded themselves and established an independent identity as Berkshires Jazz with a mission to present jazz performances and promote jazz education throughout the year, including the Pittsfield City Jazz Festival. Scheduled for October 9-18, this year's line-up includes a "jazz crawl" over Columbus Day weekend at some of the region's best restaurants and lounges, as well as headliners Frank Vignola, Grammy winner Randy Brecker, and the Greg Hopkins Jazz Orchestra performing the following weekend.

  • For art in the most picturesque setting, head to the newly expanded Sterling and Francine Clark Art Institute. The couple's private collection was opened to the public in 1955 and has since grown to include several exhibition and educational buildings amid a sprawling 140-acre campus. Be sure to visit "Thomas Schütte: Crystal" (through December 31, 2015), the German artist's first site-specific, large-scale architectural artwork installation in the U.S.

  • The Secret is Out: Winter Visits

    Snow-dusted trees and clear skies set the scene for winter in the Berkshires. Cozy up at these locales:

  • You may feel as though you've walked into a Dickensian novel as you stroll among the estate at Cranwell Spa & Golf Resort, a Gilded Age dream that dates back to 1853. A range of accommodations is offered for any budget. Be sure to allow time to cross country ski or snowshoe amid the six miles of groomed trails, or go for a slippery spin at the on-site skating rink. At the end of the day, the Spa at Cranwell offers everything from facials to massages as well as a signature Grand Mosaik dry float body treatment.

  • Stay warm with a visit to Barrington Coffee Roasting Company, where you can enjoy a cup of fair trade, environmentally sustainable java. Better yet, learn how to taste and brew the perfect cup by participating in the newly launched cupping class where participants will roast their own coffee, learn about trade standards and methods of evaluating, and of course, go home with a bag of freshly roasted beans.

  • MASS MoCA, one of the world's largest multi-disciplinary arts centers set within a former 19th century factory, recently received a $25.4 million state grant to continue its expansion and help position it as the largest contemporary arts center in the country. The Sol LeWitt installation took nearly six months to implement with a team of 65 artists and will be on display through 2033. Other temporary exhibits of note this winter include Barbara Takenaga's large-scale installation as well as "Clifford Ross: Landscape Seen & Imagined," which includes photography, multimedia, and other juxtapositions of abstractism and realism.

  • Cozy Spring Comforts

    Some may call it mud season, but we look at it as the best time to take advantage of lower rates and enjoy the Berkshires before the onslaught of the summer season. Plan your spring getaway with these helpful tips:

  • Are you ready for an aerial experience? Head to Ramblewild, a tree-to-tree adventure park set in the middle of a 1,400-acre New England landscape. Depending on your thrill capacity, Ramblewild offers eight different obstacle courses, consisting of 15 to 17 elements each, including high wires, zip lines, cargo nets, and more.

  • Stock your home bar with a visit to Berkshire Mountain Distillers, where you can tour the artisan spirit producer's facilities. The Berkshires' first legal distillery to open since Prohibition, BMD's small-batch production includes Greylock and Ethereal gins, Ragged Mountain rum, Ice Glen vodka, Berkshire bourbon, and New England corn whiskey.

  • For a closer look at the latest food trends, Berkshire Farm & Table Find.Eat.Drink. and the legendary Red Lion Inn produced a video that showcases some of the local food artisans and producers who continue to make their mark in the region:

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  • Matthew Wexler is EDGE's Senior Editor, Features & Branded Content. More of his writing can be found at Follow him on Twitter and Instagram at @wexlerwrites.