Bringing It Home at ButtonBall
- Laura Mars
- 4 hours ago
- 7 min read
LOCAL GIRL AND FORMER CAST MEMBER OF REAL HOUSEWIVES OF NEW YORK CITY BUYS THE EGREMONT VILLAGE INN AND BARN TO BUILD COMMUNITY
By Laura Mars Photos by Gregory Cherin
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, executive director of the Southern Berkshire Chamber of Commerce. Dan Thomas, co-owner of the South Egremont Spirit Shoppe, agrees. “Not that it was an eyesore, but it’s easier on the eyes now,” he says. He also likes that ButtonBall is not just a late-night spot, but offers daytime, family-friendly events. And while a music venue in the middle of town will always have to deal with noise issues, he says that most of the inn’s neighbors he talked to say it’s not a problem.
Wanting to see ButtonBall in action, I walked into the inn’s front parlor amid lively chatter from the dining room, honestly a bit nervous to meet the former Housewife. I found her, her husband, and their pooch, Jesse, warm and charming. With a ready smile, Heather was excited to take me on the ButtonBall journey. I blurted out my first question: “Why UFO wallpaper in the bathroom?”
“You know the UFO thing here was real, right?” Heather says, referring to an “off-world” incident in Egremont and surrounding towns on September 1, 1969. (I vaguely remember hearing about it. Google filled in the blanks of the incident that rocked the Berkshires.) “We wanted to take the scary out of the UFO thing, have fun with it,” she says of the wallpaper she put in the bathroom, and she points to artwork in the room we were in: historical photos and illustrations of the inn that she had superimposed with UFOs, alien figurines on the shelves, all designed to embrace the UFO event in a lighthearted way. ButtonBall hosted an Encounter Festival on August 31, which was not only a wonderful day for the community but also gave lens to zoning issues that are attached to the word “festival.” Heather says it will become an annual event.
With aliens out of the way, we got down to the very real world of renovation. Bringing electricity and HVAC systems up to code were herculean tasks. Removing yards of extension cords from trees—and many of the trees themselves—had to happen before they could get insurance. All 12 guestrooms (six in the main building, four in the attached apartment, and two in the carriage house) were lovingly renovated.
The inn is now a delicious blend of rustic, modern, and quirky. The new innkeeper points out vintage wallpaper and furniture, antique mirrors, a restored luggage rack, and Tillett hand-screened prints. Signature bedding oozes modern luxury throughout. She emphasizes, with emotion, that they could not have opened so quickly or with so much pizzazz without the help of her friends. Designer Patrick McBride, fourth generation owner of Tillett Textiles in Sheffield, collaborated with Heather on interior design. Superstar interior designer Courtney Novogratz, who has a stunning home in Egremont, told her that you can’t have all new or all old. Longtime friend and fellow entrepreneur Jennifer Nacht, former executive director of the Lenox Chamber of Commerce, helped organize the business side of ButtonBall and continues to be involved with special events. “The Barn is where we would all go and have fun—the local Honky Tonk,” recalls Jennifer. “I wanted to be part of bringing it back.”
As we step out the back of the inn, The Barn looms a few hundred yards behind and towards the right. The carriage house, a few steps beyond The Barn, holds guest rooms for the talent and other guests and room for soon-to-be-offered yoga. The property comprises nine acres. Heather points out the lawn that was cleared for outdoor use and protected wetlands beyond. “If you just step a few inches away from The Barn, you hear a symphony of birds,” she says. “We want to preserve nature and history but move it forward in a way to attract people to our community. And the cemetery.” She points to the gravestones right past The Barn. “They are such great neighbors!”
In The Barn, we run into Jonny Rosch, that evening’s musical act and original Blues Brothers band member. “I love it,” he says about the venue. “It’s actually my kind of vibe. I built a log cabin recording studio in the Southern Catskills, very much like this.”
Leaning into the UFO theme with figurines and artwork, The Barn is also undergoing what Heather calls a balance change. “We’ll have shows that are open to everyone, no entry fee—bring your love and we’ll bring the music, like Free Sundays at 6. We’ll also have house concerts that are quiet and intimate, where people come for the artist—different listening atmospheres that are intentional, creating special experiences and nights to remember.” With the help of Jenny Rubin, who ran The Barn with her husband Nick Keene from 2016 to 2024, the docket is full well into 2026.
Jonathan recalls Jim Belushi playing The Barn in June and serenading his daughter, Ella, who was bartending. “I love this place,” Belushi told him at the end of the night.
Jonathan’s childhood friend and Heather's business partner, Doug Grabe, is the owner of seven Little Pub restaurants and The Surfside Hotel in Connecticut. Doug was introduced to Heather decades ago, and they’ve been looking for a project to partner on for a while. Doug looks for anomalies—properties that could use an upgrade and be transformed into a commercial success and a great fit for the community. Heather leans into things when she knows she can help. “There was something missing in the community that I had growing up around here,” she says of why she dove into the project. ButtonBall, whose name comes from Button Ball Lane, just 50 yards from the property, checks all the boxes.
“We’re just getting started,” Doug says of the partnership. Everything is on the table as a possibility: a Little Pub restaurant at the inn, movie and trivia nights, a meeting place for local organizations, yoga classes, walking and hiking trails, art walks, farmers markets, and events tied to topics that the wellness advocate side of Heather explores on her podcast, Health, Harmony & Heather. She hosted a women’s retreat in October and looks forward to a series of wellness weekends in the winter months.
ButtonBall also gives the Berkshires another place to celebrate the holidays. Enjoy a picture-perfect Thanksgiving Day dinner at the inn, or celebrate New Year’s with a sumptuous dinner on the Eve at the inn, dancing and food truck bites at The Barn, and a New Year’s Day breakfast back at the inn. Also available are “stay and play” packages for the holidays and beyond: Simply walk to your room after an evening of celebration and wake up to the smell of coffee!
What’s also on the table is more reality TV. A production company spent several days at ButtonBall, shooting a sizzle reel of the day-to-day reality of innkeeping, and meetings with major networks are in the works. The former RHONY star says they love the concept, love the team, and believe they can build a reality show around it. “People get excited by the Housewives. They are excited that there are more than one who live in Berkshire County.” (The other RHONY cast member is Dorinda Medley, who lives in Great Barrington and was on the show from 2015 to 2020.)
All in all, ButtonBall is rolling toward success in marathon vs. sprint mode. I left the property with Heather’s words in my head: “We are serious about two things here: quality and service. The rest is a hell of a good time.”
ButtonBall Inn and Barn
17 Main Street
South Egremont
413-528-9580