Western Mass. ‘Hilltowns’ look for a foothold

Often overlooked region banks on tourism, arts, and history for revitalization

THE ARRIVAL OF warmer weather means visitors will be flocking to the Berkshires, where a set of towns come to life as summer homes to renowned music and dance enterprises at Tanglewood and Jacob’s Pillow. They add to a year-round arts economy in the region anchored by the Massachusetts Museum of Contemporary Art in North Adams.

But visitors coming from the east, who generally zoom out the Mass Pike, are at best only vaguely aware of the nearby “Hilltowns” that dot the high hamlets and eastern foothills of the Berkshire Mountains. A collection of 39 sparsely populated communities, the Hilltowns are too far west to fall in the Pioneer Valley, with its well-known cluster of college towns, but not far west enough to be in the heart of the Berkshires and its vibrant tourism economy.

Instead, as the The New Yorker captured in a piece last fall about a small theater company based in the Hilltown of Chester, the region suffers a betwixt-and-between fate in which it “exists in a kind of insular netherworld—a dead zone of small, economically challenged former factory and farm towns.”

Against that backdrop, the Hilltowns are waging a comeback fight, working to jump-start economic activity through a creative economy mix of tourism, arts, and history, while supporting local food and small manufacturing operations. And although no Hilltown is typical—and you’d likely get the side-eye for saying so—Chester (population about 1,500) offers a prism for gleaning some of the region’s challenges, as well as its charms and assets.

The 39 communities that make up the Hilltowns region

The area has never been easy to settle, due partly to a long, steep escarpment that defines its economic geography and cuts it off from centers of commerce in the Connecticut River Valley and eastward. Subsistence farmers were slow to arrive, in the 1720s, and quick to continue further west. Situated on Route 20 amid two branches of the Westfield River, about 20 miles southeast of Pittsfield, Chester eventually became a bustling mill town. Its industrial activity took off with the discovery of emery, a rare mineral used in abrasives for industrial applications, flooring, and, yes, emery boards. By the mid-19th century, the town had established several grinding mills, a rail depot for the Boston-Albany line, and a modicum of prosperity.

But most of this activity came to a halt by the 1960s with the earlier development of synthetic emery, leaving behind legacy industrial buildings, a proud sense of local history, and a struggling economic base. As the Massachusetts tech economy took off in the 1980s and the decades that followed, Chester, with a median household income that is 75 percent that of the state, was largely left behind.

“Places like this can be a poverty vortex,” says Aaron Allen, 43, who with his 35-year-old wife Erin Patrick owns Chester Common Table, a locally sourced restaurant housed in a former saloon on Chester’s Main Street. “You lose your car, you can’t get to a job, and everything goes downhill from there,” he says, describing the isolation of rural poverty that can quickly overtake those caught in its web.

Well aware of the region’s precarious condition, Aaron and Erin (as they are known to everyone) are nonetheless investing in Chester’s future, in hopes that historical, arts, and outdoor recreational tourism will draw visitors and jobs to the area. With double-digit sales growth since launching Chester Common Table in 2016, they are developing another nearby older property, this one a former Mobil gas station and garage on Route 20, painted white and emblazoned with the iconic red Pegasus required by the company’s former branding.

Carms Restaurant after a late winter snow in March. The garage next door will become home to the new Hilltowns Visitors Center. (Photo by Catherine Tumber)

With an eye toward retaining the building’s retro exterior, they have plans for three ventures in the space, including another restaurant and a vistors center to promote the Hilltowns region. Aaron and Erin, who also works as production and operations manager for the Chester Theater Company, know that executing the turnaround vision for the town will be a challenge. But when asked about it, Erin exudes a can-do optimism that could serve as the mantra for all those working to revive the area’s Hilltowns.

“Individual action can have a huge impact in a small struggling town like Chester,” she says. 


Getting deep into the Hilltowns, as I did one wintry weekend in March, it becomes clear why its regional economy is so fragile. It shares New England’s demographic profile in acute form: predominately white and aging, it has difficulty retaining and attracting the young. Along with tourism, most residents are engaged in farming and food processing, small manufacturing, timber works, cottage industries, and other productive enterprises typical of rural life, along with “eds and meds,” the education and health care sectors that are the area’s largest employers. With populations ranging from 500 to 2,000 residents, each Hilltown has its own distinct character and priorities, which makes it difficult to act in unison when seeking policy support from the state.

The region is divided in other ways as well. It comprises parts of four counties: Hampden, Hampshire, Franklin, and Berkshire. It is broken up into multiple legislative districts, each shared with dissimilar neighbors. It is served by three nonprofit community development corporations, each with its own strategic emphases, plus the new six-town Gateway Hilltowns economic development collaborative.

Fiercely independent and proud of their rural character, the Hilltowns have long had a troubled relationship with the seat of state wealth and power in Boston, dating back to Shays’ Rebellion in 1780s. Over the years, their sense of grievance and distrust has remained at a low boil with actions such as the submergence of four nearby towns to create Quabbin Reservoir to supply Boston’s water, the effective dissolution of county government that left residents directly dependent on the state bureaucracy, and unequal per capita spending. With Greater Boston’s remarkable success in the global economy, it remains to be seen whether the Hilltowns can tap into the state’s economic vitality while preserving their autonomy and rural small-town culture.

Pittsfield native Dave Christopolis knows the terrain well. The energetic 50-year-old Goshen resident is executive director of the Hilltown CDC, which serves 22 towns in the heart of the region. He is also vice president of the Massachusetts Association of Community Development Corporations and an at-large board member of the governor’s Rural Policy Advisory Commission.

Like many in the Hilltowns, he stitches together several jobs, including part-time work as a musician—his first love. Established in 1981, the Hilltown CDC began primarily as a small-business development program, providing training and technical assistance to new and established firms, forming a bed & breakfast association, and publishing a business directory that comes out annually to this day. Within six years, the Hilltown CDC had moved into housing, constructing and rehabbing affordable dwellings, and building community centers and public-safety facilities, mainly with federal community development block grant funds that are now drying up. Over the years, the CDC has also assisted with infrastructure projects such as road repaving, septic system repairs, and accessibility upgrades.

In the absence of meaningful county government, which was abolished out this way some 20 years ago, the CDC acts as a “rogue county,” says Jeanne LeClair, economic development director for Gateway Hilltowns, with Christopolis the de facto county executive coordinating shared services and leading advocacy efforts.

A ceiling hangs over the Hilltown CDC’s economic development efforts: limits to infrastructure development and arcane zoning regulations more suited to suburban development. Not only is the area thinly settled, but the rocky geology makes it cost-prohibitive to blast for sparsely distributed natural gas lines (which the locals successfully resisted in any case) and sewer development. Service infrastructure is stretched thin as well, with just two nonprofit ambulance companies serving the roughly 600-square-mile Hilltown CDC region, and several recent school mergers due to steep drops in student enrollment. Last year, Chester and Blandford merged their police departments.

Loose zoning bylaws, along with poverty-driven demand for reliable tax revenue and super-cheap consumer goods, have also left these communities prey to Dollar General super stores. The national chain is moving aggressively into Western Mass., willing to take temporary losses while competing with local businesses operating on perilously slim margins. While it succeeded just north of Pittsfield, the company faced stiff resistance to a new store in the Hilltown of Cummington (and nearby Deerfield) and ultimately lost the fight in January. The contentious local battle was something of a “proxy” for national party polarization, says Christopolis, who hopes that lingering raw feelings won’t stall regional economic development efforts.

Dave Christopolis, executive director of the Hilltown CDC, which acts as a sort of “rogue county” to knit together efforts across the region. (Photo by Catherine Tumber)

When asked what would help stem the population loss and draw young people to the region, Christopolis is quick to say that broadband would make a huge difference to the local economy. Fast and reliable digital infrastructure would not only enable knowledge workers to telecommute, but it would also make it easier for the farmers, value-added food producers, and artisans in this fiercely rural area to market their goods to distant consumers.

Several towns are working with Comcast or WiredWest (a cooperative of municipally owned broadband services), with partial funding from the Massachusetts Broadband Institute, but coverage will not be complete without additional funding. With more internet customers for local retail and commercial services, the Hilltowns would have a fighting chance to keep the Dollar Store franchise at bay.

But Christopolis is also clear that broadband is not a silver bullet. “This is a uniquely rural area,” he says, with an escarpment location that is more challenging than in other pockets of Massachusetts rural activity. Compounding the difficulty, the US Census regards the southeastern Hilltowns as part of the Springfield Metropolitan Statistical Area. As a result of this federal designation, the region is not eligible for rural entitlement funds to support activities such as infrastructure and service buildout, and it must compete with more densely settled parts of the Census region for housing support and other types of funding.

Since that arrangement is unlikely to end anytime soon, Christopolis argues, the Hilltowns need a master rural economic development plan, one supported by the state working hand-in-glove with the area’s constituent towns and the private and nonprofit sectors. A Hilltown regional plan, he says, should include both broadband and “a multi-year strategy to redevelop a series of shovel-ready properties to address vacant mills, homes, and village centers, including some infrastructure improvements.” A rural variation on smart growth planning, the idea is to concentrate hard infrastructure, such as sewer districts, in town centers that can support housing and business clusters. He adds that planning should also “establish a local small business brand cooperative to move locally made products through a supply chain, and include a marketing plan to new homeowners, once broadband is complete, with some down-payment assistance—all while educating neighboring areas about the value of supporting sustainable rural communities.”

Christopolis presses for this vision locally and through the state’s Rural Policy Commission and legislative Rural Caucus, both established in 2015 to pool interests in a way similar to the Gateway Cities initiatives established a decade ago. Currently, the commission is researching establishment of a statewide Office of Rural Policy, similar to those in Maryland and Pennsylvania, with a full-time executive director.

“Economic development is a bit harder in the Hilltowns than in other rural areas of Massachusetts,” says state Sen. Adam Hinds of Pittsfield, whose sprawling district covers most of the Hilltowns and all of Berkshire County. “It is farther from the state capital and it has less access to state transportation networks linked to regional and national population centers.”


In Chester, the same wariness of national chains that helped Cummington beat back a Dollar General store proposal was crucial to Aaron Allen and Erin Patrick’s ability to acquire the former Mobil station building they’re now redeveloping.

The former owners ran the small, much-beloved Carm’s Restaurant out of the 1863 building for some 50 years and refused to sell it to Cumberland Farms, preferring to pass it on to an independent enterprise. Eventually, it was purchased by Erin and Aaron. They plan to reopen Carm’s as a local breakfast-and-lunch gathering place, with much of the original 1930s furniture and fixtures intact and an additional “rural Starbucks” vibe inviting to younger and digitally inclined patrons.

The lunch counter at Carm’s, which Aaron Allen and Erin Patrick aim to preserve when they reopen the restaurant. (Photo by Catherine Tumber)

Next door, in the front of the old garage, they will lease space for a new Gateway Hilltowns Visitors Center, with renovations and a part-time position supported by a $75,000 earmark in last year’s state economic development bond bill. It will be operated by 43year-old Bryan Farr, an enthusiastic bear of a man who heads the nonprofit Historic US Route 20, established in 2014, which aims to turn the old roadway running clear across the country from Boston’s Kenmore Square to Newport, Oregon, into a historic tourism trail through pre-Interstate small-town America. Route 20 overlaps with the Jacob’s Ladder Scenic Byway, the designation for a 33-mile stretch of the road running through Western Mass. from Russell to Lee.

More controversially, the large space in the back of the garage will be rented to a marijuana cultivation firm. Although 70 percent of the town supported state legalization, vocal opponents had to be reassured that this would be a production facility with strong security, not a retail shop with big traffic and users milling about.

As with their restaurant Chester Common Table, which also hosts live music and community events, at Carm’s Aaron and Erin expect to serve both a local clientele and visitors drawn to the town’s other offerings.

With an active historical society, the Chester town center is a designated historical district that hosts three history museums—including a railway museum, housed in the original 1841 depot, that attracts industrial-heritage and rail buffs. The town itself is adjacent to Worthington, ground zero for Shays’ Rebellion and home of instigator Daniel Shays. Both towns sponsor self-guided walking tours of the now-overgrown 18th-century terrain and other historical programs established with Mass Cultural Council support.

The town is also home to the professional Chester Theater Company, which opened in 1990 and where thespians Aaron and Erin, who grew up in Beacon, New York, originally met. The theater, which runs summer productions out of the Chester Town Hall, can be viewed as part of a seasonal arts cluster that includes Jacob’s Pillow Dance Center in next-door Becket.

Another asset, this one attractive to outdoor recreational enthusiasts, is the Chester-Blandford State Forest. Privately guided hikes are available for day trippers, if you know where to look, but the state Department of Conservation and Recreation has provided little marketing or wayfinding for out-of-towners, and there are no inns in Chester (or its five nearby sister Hilltowns) for longer stays.

“The money doesn’t stay here,” says LeClair, the economic development director of the six-town Gateway Hilltowns, which is supported in part with state Community Compact funding. Much as the area needs its Airbnbs, LeClair would like to see at least some of them converted to taxable bed and breakfast businesses. Among many other initiatives, she’s also looking into state support for the carbon capture performed by the heavily forested area. As it stands now, only 35 percent of the town’s land is taxable, and payments in lieu of taxes for state-owned land remained flat at just $16,200 for fiscal year 2020.

Chester Common Table, which opened in 2016 and has seen double-digit sales growth. (Photo by Catherine Tumber)

Despite the new buzz of activity in Chester, tourism in the town could use a boost. Economic development in the Hilltowns faces serious “logistical frustrations,” says Erin, with minimal access to groceries, gas, and high-speed internet, and local decision-making that involves a “push-pull” between “more services and support and preserving historic buildings and rural heritage.”

As a result of these conflicting claims and the fact that the entire town votes on the budget, “Chester town meetings are active,” says Aaron, who grew up in Pittsfield. “There is real discussion about minutiae, getting into the nuts and bolts. Everyone has the same goal of ensuring the town’s economic success, but do you do it by bringing in new industries or Dollar General?”

When asked whether national political affinities play out in local politics, given that 55 percent of the town voted for Trump in 2016, he says, “people are too interdependent for that. They can’t afford to cut ties. They are pragmatic and civil about specific local issues, and they are willing to listen. People argue about national politics at the bar.”


Although piecemeal efforts are helping the area hold steady, leaders in the region are looking to do better than just tread water. “We need state government to dedicate resources to a rural regional economic development plan,” says Christopolis. “I think Massachusetts can see the Hilltowns as an asset for recreation, preservation, tourism, and boutique businesses. State support can help make this happen.” And once it does, he says, “then we can engage our local Hilltown residents in determining their own destiny.”

On the ground, “it helps that the Republican governor and lieutenant governor are paying attention,” says LeClair. Thanks in part to their support for climate change measures and small independent businesses, she says, “sustainable is not a dirty word” among those in the Hilltowns who lean politically to the right. Residents understand that coal is over and that solar “just makes sense,” she says—although many resent that China is “winning” the solar manufacturing game.

In the recent round of 30 Green Community designations announced by the Baker-Polito administration in December, six are in the Hilltowns, which one vocally conservative Worthington leader proudly rolls out as a selling point. “Self-determination and control are central to rural America,” says LeClair, who hails from a farming village of 800 people in Missouri. As long as these values are respected, she continues, most conservatives see that “good green jobs can put people to work.”

“Chester is really poor,” says Erin Patrick, yet residents are suspicious of government support and out-of-towners telling them what to do. The state can help put down good educational, transportation, and infrastructure bones, but the feeling is strong that the locals should be in charge.

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Which is why Erin and Aaron don’t want to “cultivate the perception that their restaurant is elite,” says Erin. Chester Common Table has become a seasonal tourist destination. But around town it is known as a “fancy restaurant with reasonable prices,” she says, a place whose name telegraphs the message that it’s a place where all are welcome year-round. She said they look forward to running the more modest Carm’s the same way.

Catherine Tumber, a MassINC Gateway Cities Innovation Institute fellow, is the author of Small, Gritty, and Green: The Promise of America’s Smaller Industrial Cities in a Low-Carbon World.