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Cheesy Road Trip: Western Massachusetts


Wedged between the more well-known cheesemaking regions of upstate New York and southern Vermont, the rural counties of western Massachusetts—Berkshire, Franklin, Hampden, and Hampshire—have a cheesemaking reputation of their own dating back to the Jeffersonian era. In the spring of 1801, John Leland, a Baptist preacher in this northwesterly corner of the Bay State, solicited enough milk from the wives of the farmers in his flock to make a cheese the size of a wagon wheel. This mammoth cheese from Cheshire, the area now divided into the towns of Adams,Cheshire, Lanesboro, New Ashford, and Windsor, was aged and presented to Virginia Republican Thomas Jefferson because the farmers, who had faced persecution and state-mandated support for Congregational pastors under previous administrations, favored the new president’s zeal for separation of church and state.

The round was made in the cheddar style from the milk of 900 cows, formed inside a commandeered cider mill, engraved with the motto “Rebellion to tyrants is obedience to God,” and transported via sleigh, barge, and sloop 500miles south to Washington, D.C. Jefferson praised both the 1,230-pound cheese and its makers, but as he opposed the gift-giving custom on principle, sent a $200 donation (less than half of fair marked price at the time) to Leland’s congregation as a gesture of gratitude.

Modern day owners and operators of the small dairies that still dot the picturesque rolling hills and valleys in this part of the world are an independent sort and likely don’t vote as a block for any candidate as they did in Leland’s time. But it is widely evident that many still separate curds and whey for a value-added product that helps sustain their farms economically.

Given that historical, cultural, and natural attractions are everywhere in Western Massachusetts, traveling there is a year-round possibility. Hiking and camping in state parks are three-season propositions. Performing arts like the Boston Symphony Orchestra at Tanglewood in Lenox; Jacobs Pillow dance festival in Becket; and the Williamstown Theater Festival abound in summer. Foliage blooms in autumn. Ski slopes operate as soon as it snows. And museums that feature anything from Norman Rockwell’s America in Stockbridge to the new world of modern art at Mass MoCA in North Adams are open year-round.

Having a cheese-forward lunch at the ready for whatever perfect picnic spot might be right around the bend is a particularly good idea in this part of the world.

Cheesemakers To Visit

Rawson Brook Farm, Monterey

Monterey Chèvre, which holds seven first- or second-place American Cheese Society awards, was born on this goat farm in 1983. Cheesemaker Susan Sewall and her husband fashioned their operation into a wooded area on her family’s property using chainsaws. Sewall still operates the dairy with its low-fenced paddocks, unassuming barn, and small cheese room. She sells her chèvre plain and with herbs in smaller quantities than in the past from a self-serve stand at the end of the drive during daylight hours between March and January.


High Lawn Farm, Lee

The Jersey girls living on this hillside farm in the heart of Berkshire County have a great view of Laurel Lake and October Mountain, the largest state forest in Massachusetts. Generations of Jerseys have enjoyed this view as they have supplied milk to area residents since the 1920s. Two years ago, Roberto Laurens, Jr. and Matt Schwizer started making a host of farmstead cheeses, ranging from the bloomy rind High Lawn Queen that turns gooey as it sits to a tangy, almost chewy, aged cheese called Wilde Field. If the cheese sold in the farm’s year-round, on-site shop isn’t enough to tempt you to stop on a warm summer’s day, might we suggest the ice cream?


Cricket Creek Farm, Williamstown

Owned by Jude Sabot and her son, Topher, since 2002, this grass-fed dairy sits on protected land. Its flagship homestead cheese, Maggie’s Round, inspired by Italian alpine tomas, is semi-firm, made from raw milk, and aged up to nine months. Larger rounds, made by same recipe but cured for up to 24 months, become Maggie’s Reserve. Tobasi is made from raw milk in the taleggio style while the dairy’s camembert derivative, Berkshire Bloom, is made from pasteurized milk. The honor system rules the farm stand, which is open daily from 7 a.m. to 7 p.m.


Grace Hill Farm, Cummington

Since 2014, Jasper Hill Farm alum Max Breiteneicher and his wife, Amy, have been making raw-milk cheese from their small, pastured herd of Normande and Ayrshire crosses. You can find Grace Hill’s Cheesecake, a tall, tangy, white mold cheese; creamy, mostly mild Hilltop Blue; and cloth-bound farmhouse cheddar on many local restaurant menus. The Breiteneichers also sell their cheese at many farmer’s markets and coops, and from April to November at their own farm stand.


Side Hill Farm Yogurt, Hawley

Side Hill Farm is well known in these parts for the organic yogurt Amy Klippenstein and Paul Lacinski have been making for decades. In 2020, they sold the farm, but not the yogurt operation, to farmers Gus and Kyra Tafel who now own all the cows (as well as many other animals) you see when you visit what is now called Meadowsweet Farm. Gus and Kyra milk the cows, and Amy and Paul make the yogurt and crème fraîche that’s sold alongside Meadowsweet Farm raw milk and pastured meats in the farm shop. The couples also send milk up to Grafton Village Cheese in Grafton, Vermont to have it made into 1- , 3- and 5-year-old School House Cheddar. The cooperation is a lesson in successful farm succession.


Other Noteworthy Stops

Rubiner’s Cheesemongers & Grocers, Great Barrington

As witty as he is knowledgeable, Matthew Rubiner is single mindedly set on giving customers a taste of great cheese from around the world and all the accompaniments that could possibly be served alongside it. If it’s a grilled cheese you’re after, check out Rubi’s Café next door.


Corsello Butcheria, Easthampton

Vincent Corsello’s popular butcher shop was inspired Italian butchers at the Mercato di Testaccio in Rome. He and his family source the meat they expertly cut fresh to order, transform into charcuterie, or put into sandwiches, from farms throughout the Pioneer Valley.


Picnic Recommendations

Around almost every bend in the roads in Western Massachusetts, you’ll find a formidable place to set out your picnic blanket. But two especially perfect ones are Bartholomew’s Cobble in Sheffield, named for its two rocky knolls—or “cobbles”—rising above the Housatonic River valley, and Chapel Brook Falls in Ashfield that shows off the rugged forest of the Pioneer Valley region and the streams that roar or trickle with the seasons. Both land conservation properties are managed by the non-profit The Trustees of Reservations.

Where To Stay

Chambery Inn, Lee

The Chambery Inn in Lee is a nineteenth-century schoolhouse turned boutique hotel in this small mill town. Enlightening eight-foot windows, embossed thirteen-foot ceilings, and the original blackboards contribute to the ambiance of this gracious Inn.

Hotel Northampton

Built in 1927, Hotel Northampton exudes historical elegance in its common areas, has modernized guest rooms, and sits within walking distance of this quaint city’s cultural and culinary offerings.


Want to keep traveling? See what other stops are on our cheesy road trip here.

Christine Burns Rudalevige

Christine Burns Rudalevige has been a working journalist for 30 years and has considered cheese her favorite food group for even longer. Ten years ago, when she attended culinary school, one of her goals was to write for culture.

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