It was ‘so good to see you’: Rosey’s to close Aug. 14

Rosey’s, at 2987 Church St. in Pine Plains, will close its doors on Monday, Aug. 14.
Photo by Matt Petricone
PINE PLAINS — Come Monday, Aug. 14, the residents of Pine Plains will have one fewer place to land for coffee, breakfast and lunch. Announced over Instagram on June 21, the closure of Rosey’s will end a run of just under three years.
Jamie Gerber, Rosey’s owner and manager, came to the decision to close shop for a variety of reasons, but chief among them was the impending departure of Rosey’s chef, Brit Ko. Ko is off to Rutgers to get a master’s degree in poetry, and to Gerber, the departure of a chef who is “such a creative and thoughtful cook” and who meshed so perfectly with Rosey’s fit and feel presented an opportunity for reevaluation. “There’s a part of me that thinks that I don’t want to work with anyone else,” said Gerber.
“It has been such a great adventure, and I’m very pleased to know so many more people in town, and feel involved in Pine Plains. But to be honest, I don’t totally enjoy running a business. If you want to make it as a business owner, you have to want to make money, and I’m not motivated by that.”
What Gerber has been motivated by is the community they’ve found in town and at Rosey’s. Gerber first moved to Pine Plains from New York City to work at Chaseholm Farm. They had little to no experience farming, but Sarah Chase, co-owner of Chaseholm with her brother Rory, was an old college friend and took a chance on Gerber.
“Chase took a big risk in taking me on, and it was truly a lifesaving gesture. … [She was] so incredibly generous, in terms of bringing me into her community,” Gerber said.
While at Chaseholm, Gerber began to operate a food cart that offered coffee and pastries. Customers were mostly neighbors and friends visiting Chaseholm’s farm store, and Gerber described that first venture as a way, in part, to “trick friends into visiting us at the farm.”
From that food cart, Gerber eventually built toward a business, and in October 2021, they signed a lease on the space at 2987 Church St., marking the beginning of Rosey’s. That decision to open a cafe/restaurant arose from Gerber’s love of sharing food with people, but also a desire to “create a space where my friends and neighbors could share food that was also grown by our friends and neighbors.” Indeed, a hallmark of Rosey’s menu has been a wide variety of food produced at Chaseholm, from farm-fresh eggs to tender pork—and Gerber gave full credit for the delicious dishes that arose therefrom to Ko and the kitchen staff.
But another element of Gerber’s decision to start Rosey’s had to do with Rosey’s namesake and its motto. The store is named for Sarah Chase’s mother, Rosey, with whom Gerber has developed a strong connection.
“Rosey and her twin sister, Tully, are always saying, ‘So good to see you.’ I love that spirit [of] I’m so glad to see you, I’m so glad to connect, I’m so glad you’re here. I’ve always felt very seen and loved by Rosey, and I wanted to cultivate a space that had that feeling to it.”
And while Gerber was able to build that atmosphere at Rosey’s, over time, the demands of running a business began to take a toll: “You’re always working, there aren’t really any days off. At the beginning, there literally were no days where I wasn’t there. It’s really hard to step away, have a boundary, not answer a phone call, do orders, answer an email.”
For that reason, plus continual staffing difficulties—an issue plaguing many businesses in the region—Gerber came to the decision to wrap up the Rosey’s chapter of their life. And by way of reflection on that chapter, Gerber had nothing but positive things to say.
“I feel unbelievably grateful for the friends and community that I’ve got here. People have been so kind and generous to us. Whether that was my friends who were sanding the floors for weeks on end, or our neighbors bringing us pastries every week. I have just been struck by people’s openness and generosity.”
In terms of what’s on the horizon for Gerber, they’re heading back to Chaseholm Farm to work with Sarah. And while what they’re looking forward to most at the moment is a bit of rest and distance from managing a business, they hope to continue to do catering, pop-up food events, and maybe even bring the food cart back to life. The biggest project for Gerber after Aug. 14, however, will be making peace with an ending, even if the journey itself was successful.
“We really want things that we love to last forever. But they don’t, and it’s okay that things end. It’s okay that things change. I’m really excited for the next folks that go into that space and get to try something out. And I’m really excited for Brit’s next adventure. But it’s bittersweet for sure.”
From left, chef Brit Ko and owner Jamie Gerber of Rosey’s in Pine Plains, which will close on Aug. 14. Photo by Matt Petricone
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/.