WHEN HEATHER THOMSON SCHINDLER learned that the former Egremont Village Inn and Barn were for sale, she saw her next big opportunity. Following careers in fashion, business, and reality TV, she partnered with hospitality entrepreneur Doug Grabe to purchase the property that was known for hosting some impressive live music. After major renovations inside and out, The ButtonBall Inn and Barn opened on Memorial Day, bringing music back to The Barn and guests back to the inn.
B y L a u r a M a r s // P h o t o s b y G r e g o r y C h e r i n
WHEN HEATHER THOMSON SCHINDLER learned that the former Egremont Village Inn and Barn were for sale, she saw her next big opportunity. Following careers in fashion, business, and reality TV, she partnered with hospitality entrepreneur Doug Grabe to purchase the property that was known for hosting some impressive live music. After major renovations inside and out, The ButtonBall Inn and Barn opened on Memorial Day, bringing music back to The Barn and guests back to the inn.
The vision for ButtonBall is to be the heart and soul of the community: a place to celebrate culture, enjoy nature, and gather around the table and on the property for a myriad of events, from game nights to farmers markets. After moving at breakneck speed for six months to get the place up and running, Heather is now taking a breath and engaging with the town and community to take the steps necessary to make the vision reality.
A local girl from neighboring Copake, New York, Heather became a cast member on The Real Housewives of New York City( RHONY) in 2012, where she stayed for three seasons before the craziness was too much.“ There was a beginning, a middle, and an end for me as a full-time cast member— I had to stay true to myself,” she says.
Before RHONY, she had made a name for herself as a fashion designer in New York City. She worked with Calvin Klein, Ralph Lauren, and Sean John Combs, and was co-creative director of Jennifer Lopez’ s and Beyoncé’ s labels. Then she founded the shapeware company Yummie by Heather Thomson based on her patented designs, which she sold in 2012. She credits getting her start in fashion by working at Cypress Apparel in Sheffield( later Monarch Robes whose Sheffield office closed last year). Before Cypress, Heather worked at Kenver Ltd., which just closed after a 60-year run. She also recalls
Catamount Ski Resort being practically her second home, where she skied from the age of seven, eventually becoming an instructor until she left for college at SUNY Plattsburgh, graduating with a marketing degree. Through the years, she also worked at her mother’ s longtime breakfast and lunch restaurant, The Hub in Copake, which closed in 2015.
ButtonBall brings her full circle back to the Berkshires full-time, where she and her husband, Jonathan Schindler, built a second home 24 years ago. After spending the pandemic in the Berkshires, their two children chose to go to Monument Mountain Regional High School, so they switched home base from their place on Manhattan’ s West Side to North Egremont.“ I never wanted to leave for good,” says the 55-year old entrepreneur, who knows that running a big business in a small town comes with challenges.“ I left to explore, to find my way in the world, so I could come back home. I grew up here. I understand small towns. What some call small-town mentality, I see as small-town integrity— people care, and there’ s always a way to work together. After being a Housewife of New York City on reality TV, I have grown a thicker skin. Sometimes, you have to just keep going and it will reveal— you prove that you share peoples’ values.”
“ She’ s doing an amazing job of cleaning up the property,” says Betsy Andrus, exec-
Opposite, Heather Thomson Schindler and her business partner and friend Doug Grabe in front of ButtonBall Inn.
Heather on the cleaned-up property behind the ButtonBall Inn with The Barn in the background.
Holiday 2025 BERKSHIRE MAGAZINE // 73