Outgoing Region One super reflects on teaching tenure

Superintendent Lisa Carter is retiring at the end of this month after 21 years as an educator and administrator with the Region One school district.
Debra A. Aleksinas
Superintendent Lisa Carter is retiring at the end of this month after 21 years as an educator and administrator with the Region One school district.
NORFOLK — When Lisa Carter joined the Region One school district in 2002 as a social studies teacher at Housatonic Valley Regional High School (HVRHS,) following her work with the U.S. State Department where she helped write the curriculum for teaching Foreign Service Officers how to speak Mandarin Chinese, she envisioned retiring in that role.
She never imagined her teaching position would serve as a steppingstone toward a 21-year career in education, capped by her appointment as superintendent, with responsibility for leading and managing seven schools and seven boards of education, as well as one regional school board, during one of the most tumultuous times in the history of American education.
In an interview in late May at The Hub in Norfolk, her hometown, Carter reflected on her tenure with the Region One school district, from which she is stepping down at the end of June.
“I’ve done a lot of things, but this has been the most rewarding career that I’ve had in my life. I never thought I’d have the opportunity to learn from so many people, and for me to have impact on the lives of so many people, and to send our students out into the world with big dreams and aspirations, along with the confidence to achieve those dreams,” said Carter.
Prior to becoming superintendent of the Region One school district — which includes, in addition to the regional high school, six elementary schools: Lee H. Kellogg, Cornwall Consolidated, Kent Center, North Canaan Elementary, Salisbury Central and Sharon Center— she held the position of assistant superintendent from 2017 to 2020.
Carter, who earned a Bachelor of Science degree in Mandarin Chinese and a minor in Business from Georgetown University, a master’s in business administration from the University of Southern California and a second Master’s in Educational Leadership from Central Connecticut State University, served as Salisbury Central School Principal from 2011 to 2017, after teaching social studies at HVRHS for nine years, from 2002 to 2011.
The China Connection
Carter, who has two sons, was born in Georgia in 1956. “I lived there for 10 days. My father was in the service and was sent to France for 18 months. Today, at age 91, he still feels bad for missing the first 18 months of my life,” she explained.
She and two younger brothers grew up Pittsburgh, and she eventually went off to college at Georgetown University, where she majored in Chinese and minored in business. Carter spent her junior year in Taiwan. “This was before you could go to Mainland China. It helped me with the fluency of the language,” she recalled.
After graduation, she landed a job with the U.S. State Department. By that time, she noted, Mainland China opened up and people were being assigned there. Carter worked with a team that created curriculum used to train diplomats looking to relocate to Bejing.
“I had always thought I wanted to be in the diplomatic corps,” she explained. So she attended a diplomatic language learning center in Arlington, Va., in preparation for her service exam. “I really wanted to go to Mainland China, which had been closed off to the rest of the world, and wanted to be one of the first people to see what it was like.”
Carter recalled the disappointment of finding out that it was “highly unlikely” that she would be posted in China as a junior member of the Corps, as it was a “plum assignment” reserved for longer tenured staff.
The then 23-year-old received another disappointment upon learning that a job as an office assistant with Dravo Corporation, where she was to assist with opening their office in Beijing, fell through when they did not get the contract.
For the next five years, Carter worked closely with the engineering teams on Union Oil Company in California. “The development was so rapid,” she recalled. “The Chinese people are so friendly and so loving and it was really great to get to know them and see them come alive and open themselves up to industrialization. And I got one of my dreams.”
After meeting her future husband, she moved to New York City, got married and had two sons, now ages 27 and 30. She was hired by real estate maven Barbara Corcoran, selling co-ops and condos. Referring to her new boss, “she was a pistol,” noted Carter. “I liked the people in the business, but I did not like the business.”
The family relocated from the Big Apple to Norfolk, where they had a “big circle of friends.”
“I always wanted to be a teacher, but I didn’t think the kids would like me. I was pretty serious as a young woman and didn’t have a lot of confidence and belief in myself.”
Prompted by teachers at the high school, she applied to Salisbury Central and HVRHS as a substitute teacher, hoping to get hired as a history teacher. She obtained her teacher certification and a year later was hired full time when a position opened up at the high school.
‘The ideal leader’ during a volatile period
While at the high school, Carter opened the relationship with the Shandong Experimental School in Jinan, China, and introduced the Civic Life Project, a program that teaches civics through the production of short documentary films.
“I loved teaching there, and I had great colleagues,” she noted. “We were always keeping track of current events and helping kids see the connections between what came before and what’s happening now.”
In many ways, Carter’s background shaped her success as a teacher and administrator.
HVRHS Principal Ian Strever put it this way: “Lisa’s experience prior to becoming a teacher brought a worldly and innovative thinker to Region One. Her creative and flexible problem solving made her the ideal leader during what has been one of the most volatile periods in American education shepherding us through a pandemic, massive societal change, and a wave of legislation that has redefined the purpose of school.”
In 2020, Carter had settled into her role as assistant superintendent, when the superintendent’s job opened up.
“They chose me and believed in me in a very difficult time, supported by every single board member and a 50-person transition team,” Carter recalled. The group met weekly and was tasked with “making decisions on how to open up the schools when very few schools were doing that. As stressful as that was, it was so much better for the students than to be at home and on the computer.”
From nurses to bus drivers, paralegals and teachers, town and state health and education officials, as well as the Litchfield County superintendents’ group, “everyone leaned in and every person touched my life and I touched theirs in a really meaningful collaboration.”
Patricia Mechare, chair of the Region One Board and the Lee H. Kellogg Board of Education, praised Carter’s leadership and flexibility during that tumultuous time. She described Carter as a “wonderful partner to all our schools and a very effective superintendent.”
As for what comes next for Carter, she is looking forward to the next chapter in her career as Assistant Executive Director with EdAdvance in Litchfield, which is a full-time position, “but will not demand as much of my time.”
While playing outside in the early post-pandemic days, Berkshire Busk! founder Eugene Carr had an epiphany: why not expand the idea of performing on the street (aka busking)into a full-fledged festival in Great Barrington?
As an entrepreneur and cellist, Carr envisioned a well-organized jamboree featuring regional talent, including musicians, acrobats, storytellers, fire-eaters, and more. He formed a team, connected with local businesses and the town of Great Barrington, and launched Berkshire Busk! in 2021. Since then, Berkshire Busk! has grown into a summer staple for Great Barrington.
In the summer of 2024, over 25,000 people experienced Berkshire Busk!. The festival is free to the public, provides a big boost to local businesses, and spectators can tip performers.
Busking takes place all over the world, either organized by individual performers or via busking festivals. Artists like The Roots, Tracy Chapman, Phoebe Bridgers, and Old Crow Medicine Show have all cut their teeth performing on the street.
General Manager Carli Scolforo is a Berkshire native with a love of music and writing. She can often be seen roaming the streets of Great Barrington, making sure everything’s in order, and serves as the festival’s face on social media.
“This year is the fifth anniversary of Berkshire Busk!, and it’s been an amazing summer,” said Scolforo. “We were able to welcome back a lot of our favorite performers, and bring in some new experiences as well. After getting rained out last year, we were able to host our first outdoor movie night in partnership with The Triplex Cinema and the Boondocks Film Society.”
Scolforo added, “This summer, we also introduced our first Open Mic Night, hosted by local recording artist and music producer Jackson Whalan. We were really pleased with the turnout of talent. The sheer amount of talent that’s hidden within an hour or so drive of Great Barrington always astounds us.”
Local businesses sponsor various busking spots, like the Berkshire Money Management Stage in the parking lot between the Triplex Cinema and Mama Lo’s BBQ. Typically, buskers bring their own amplification, while there are few spots — such as Berkshire Mountain Distillery in Sheffield — provide power.
Berkshire Busk! will end its season with a fireworks display on its last night on Saturday, Aug. 30.
Berkshire Busk! is endorsed by the Select Board of the Town of Great Barrington and is entirely supported by sponsorship fees from companies and organizations, as well as philanthropic donations from granting organizations, individuals and the Town of Great Barrington.
It operates under a fiscal sponsorship agreement with the Nonprofit Center of the Berkshires and participates in Mass Cultural Council’s Card to Culture program — in collaboration with the Department of Transitional Assistance, the Department of Public Health’s WIC Nutrition Program, the Massachusetts Health Connector, and hundreds of organizations — by making cultural programming accessible to those for whom cost is a participation barrier.
For more information, visit: berkshirebusk.com
What if the dog onstage was played by a person? That’s the delightful twist in A.R. Gurney’s “Sylvia,” opening at the Sharon Playhouse on Aug. 29. In this clever and heartfelt comedy, the title character — a stray pup who disrupts the lives of a married couple — is portrayed not in costume but by an actor who brings insight, charm, and chaos to the role.
Stepping into Sylvia’s paws is Jen Cody, who is returning to the Sharon Playhouse in a starring role for her third year in a row, ready to bring this spirited dog to life. She’s joined by Jonathan Walker as Greg, the middle-aged man smitten with his new four-legged friend, and Jennifer Van Dyck as Kate, his wife, whose patience and identity are tested by Sylvia’s sudden presence in their home.
Directed by Colin Hanlon, this production balances elements of comedy and emotional depth. Gurney’s script may be filled with laughs but at its core, “Sylvia” explores loyalty, companionship, and how love sometimes arrives in unexpected forms. The play premiered Off-Broadway in 1995 and has since become an audience favorite for its wit, warmth, and originality.
Rounding out the cast is Sienna Brann, taking on a trio of roles that highlight the play’s comic versatility. The design team includes Christopher and Justin Swader (scenic), Kathleen DeAngelis (costumes), Bobbie Zlotnik (wigs), Wheeler Moon (lighting), and Graham Stone (sound), ensuring the story is grounded in a fully realized world, albeit one occasionally seen from a dog’s point of view.
Performances run through Sept. 7 at the Sharon Playhouse. For tickets and more information, visit sharonplayhouse.org.
Paul Chaleff’s exhibit at Mad Rose Gallery in Millerton.
The unofficial end of summer is here, and while some of us may mourn the shortening days and cooler nights, the culturally-inclined denizens of the Litchfield Hills, Berkshires and Taconics have plenty to look forward to.
During Labor Day weekend, visit one of the offerings below, and maybe even take home a watercolor, rug, or locally-crafted wooden bowl to ready your home for the indoor season ahead.
Kick off the weekend with libations and bites from legendary New York City importer Rosenthal Wine Merchant at Mad Rose Gallery (5916 North Elm Ave., Millerton). The evening will mark the end of Paul Chaleff’s ceramics exhibition, which closes at the end of the weekend. Ashley Gilbertson and Franco Pagetti’s photography exhibition “Fragments in Time,” which has been extended through Sept. 21, will also be on display.RSVP by emailing info@madrosegallery.com.
Head to the Cornwall Library (30 Pine St., Cornwall) for its seventh annual weekend-long Art Sale, and peruse an endless supply of prints, posters, watercolors, photos, paintings and more, with price tags ranging from a very reasonable $20 to much greater sums.
The Library has announced that this year’s selection will “run the gamut from the antique to the contemporary, from the jazzy and colorful to the classic black and white, from realistic to abstract.” Thanks to generous donors, the sale will feature works from notable artists such as Amedeo Modigliani, Enrique Chagoya, Marc Simont, Leonard Baskin, Ruth Gannett, Robert Andrew Parker, Nicole Eisenman, R. H. Quaytman, and others, as well as a special exhibition of vintage photos, paintings and posters from late artist Duncan Hannah.
For more information and hours, visit cornwalllibrary.org/labor-day-art-sale/.
Visit the Barn at the Pine Plains location of beloved antiques and décor purveyor Hammertown (3201 NY-199, Pine Plains) and find the coffee table of your vintage dreams this weekend. Up to 75% off home goods and furniture of all kinds will be available.
This year’s iteration of the biannual tent sale features a “Makers Market” with local artisans, craftspeople and food vendors.
Visit https://shop.hammertown.com/blogs/journal/hammertown-labor-day-tent-sale for additional details and hours.
The Berkshire Woodworkers Guild, a coalition of local woodworkers that supports the local industry and its craftspeople, is hosting its 25th Fine Woodwork Show at the Berkshire Botanical Garden (5 West Stockbridge Rd., Stockbridge) this weekend. Attendees will have the chance to watch 32 masters from around the Tri-Corner region demonstrate their trades, from woodturning and Chinese joinery to boat building and French polishing.
The event will also announce the allocation of $32,000 from its scholarship fund to support 9 aspiring woodworkers, and host a silent auction of guild member-crafted pieces to support next year’s fund. Works from the artisans will also be available for viewing and sale.
Pittsfield, Massachusetts’ Hot Plate Brewing will provide frothy, local ales for swilling, while SoCo Creamery of Great Barrington will be pedaling its handcrafted ice cream for sweeter options for the whole family. Great Cape Baking Co., from Dover Plains will offer a full breakfast and lunch menu, including donuts, while Pleasant & Main from Housatonic will be providing the caffeine and crepes.Further details can be found at berkshirewoodworkers.org.
Artists across Cornwall will fling open their studio and gallery doors to welcome Labor Day culture ramblers on Saturday afternoon. An eclectic lineup of ten participating artists will show their work, ranging from pottery to sculpture paths, allowing participants a chance to enjoy the fresh late-summer weather as they meander through Cornwall’s green valleys from studio to studio.For a list of the artists, a map, and directions to each studio, visit ornwallct.org/event/cornwall-open-studio-2025/.