Cycling season: A roundup of our region’s rentals and where to ride them

Cyclists head south on the rail trail from Copake Falls.
Alec Linden

Cyclists head south on the rail trail from Copake Falls.
After a shaky start, summer has well and truly descended upon the Litchfield, Berkshire and Taconic hills, and there is no better way to get out and enjoy long-awaited good weather than on two wheels. Below, find a brief guide for those who feel the pull of the rail trail, but have yet to purchase their own ten-speed. Temporary rides are available in the tri-corner region, and their purveyors are eager to get residents of all ages, abilities and inclinations out into the open road (or bike path).
For those lucky enough to already possess their own bike, perhaps the routes described will inspire a new way to spend a Sunday afternoon. For more, visit lakevillejournal.com/tag/bike-route to check out two ride-guides from local cyclists that will appeal to enthusiasts of many levels looking for a varied trip through the region’s stunning summer scenery.
Covered Bridge Electric Bike
Instagram @coveredbridgeebike
West Cornwall:
421 Sharon Goshen Turnpike
West Cornwall, Connecticut 06796
(860) 248-3010
Closed Tuesday, open 10 a.m. to 5 p.m. all other days
Kent:
25 N Main Street
Kent, Connecticut 06757
(860) 248-3010
Open Wednesday to Sunday,
10 a.m. to 5 p.m.
North Canaan:
1 Railroad Street
North Canaan, Connecticut 06018
(860) 248-3010
Open Wednesday to Sunday,
10 a.m. to 5 p.m.
With three locations in the Northwest Corner, this outfit offers a speedier way to zoom on two wheels through the hills with electric-powered offerings for sale or rent. Rentals are available for two hour trips, half days or full days, with several sizes and models in both throttle and pedal assist e-bikes of various styles. Route maps and e-bike trainings are on offer for renters, and guided tours are available on select weekdays. Visit the website, call or email at info@coveredbridgebike.com for pricing and more information.
Each location has its own suggested routes of varying difficulty. Ethan at the Kent location says, “The first place we send people is Macedonia Brook,” the shady and bucolic state park just northwest of downtown. For a more involved ride, Ethan also recommended the quiet country roads that wind through the picturesque hill valleys to the east of town, especially off of Kent Hollow Road and toward Lake Waramaug.
Spencer, who works at the newest location in North Canaan, said that a dual-state two hour ride that takes cyclists into Massachusetts in Ashley Falls, then down into Taconic on Barnum Street and back to North Canaan via Twin Lakes Road and Cooper Hill Road, is his favorite. At the company’s West Cornwall location next to the its namesake bridge, Spencer said a classic ride is up River Road all the way to Falls Village, where riders may visit Great Falls or find some refreshment at the soon-to-open Off the Trail Café. For a longer journey, Spencer suggested continuing up Housatonic River Road north from Falls Village, where it turns into dirt and passes through gorgeous riverside farm country.
The Music Cellar
Instagram @the_music_cellar
14 Main Street
Millerton, New York 12546
(860) 806-1442
Scheduling is available via call or text 24/7
The Music Cellar is an all-instrument music school for aspiring instrumentalists, but it also rents beach cruiser bikes during the warmer months. “They’re perfect for the rail trail,” says owner and music instructor Johnny, referring to the currently 26-mile (and expanding) bike and footpath that passes just outside the storefront. “You don’t have to worry about hitting little bumps or potholes or curbs or whatever – they’re good all-purpose bikes,” he said.
Unique among area bike rentals, the Cellar offers rates starting at $20 for those looking for a shorter ride up to $50 for the day and Johnny said that he’s happy to accommodate sliding scale pricing for locals might have trouble affording the full rate. “It does help keep the lights on, though,” he said, “so if you’re renting bikes, you’re helping kids learn music!”
Johnny said that with the Harlem Valley Rail Trail at his front doorstep, he usually sends riders for a journey on the reclaimed abandoned railbed. The path currently stretches from Wassaic to the hinterlands of Hillsdale, with another 20 miles to Chatham planned to be built in the next five years pending funding. Johnny said riders can choose to head north for sweeping valley vistas below the Taconic mountains, or, “for a more shady ride, you could go south – also equally scenic, lots of wildlife. You can go all the way to Wassaic Station and jump on a train to New York.”
Bash Bish Bicycle & Tour Co.
Instagram @bashbishbicycles
247 NY-344
Copake Falls, New York 12517
(518) 329-4962
Tuesday to Saturday, 10 a.m. to 5 p.m.; Sunday 10 a.m. to 3 p.m.
Located a dozen or so miles up the rail trail is the “ye olde bike shop of the Hudson Valley,” as described by its owner Sam. The shop is just two years from its 30th birthday, and appropriately exudes small-town charm without skimping on modern equipment and service. “It’s the best little bike store in the Hudson Valley,” said Northeast resident Dan Sternberg, who was clad in a cycling kit outside the store on a sunny Friday afternoon in June.
The shop is situated steps from the rail trail, just below the deep, clear and refreshing water of Ore Pit Pond in Taconic State Park, a short jaunt from the old Copake Iron Works site and a mere half mile from the parking lot for one of the Taconic’s region’s treasures and the store’s namesake – Bash Bish Falls. Sam offers day tours to highlight the richness of the region – not only in its natural resources but also the pastoral, cultivated splendor of the farm roads that cut through the hills to the west of Route 22.
Sam says he plans to start running multi-day tours, drawing on experience he had guiding extending bike excursions while operating a lodge in Colorado. Also upcoming is a pop-up shop in Millerton for the summer, which he anticipates opening shortly once the permitting is in order.
In addition to tours, the shop offers sales, repairs and rentals, starting at $35 for a two-hour hybrid bike session ($15 for kids) and $45 for two hours on an e-bike. Visit the website for full pricing details on four hour, full day, multi-day, and weekly rates. Bookings can be made online or via phone.
Sam says he likes to direct guests towards the scattered gems of restaurants, bars and shops that pepper the rail trail corridor and into the hills and dales beyond. The Copake General Store, dishing coffee and café fare alongside locally-produced provisions is just down the road, while market and cultural center Random Harvest and beloved seafood peddler Zinnia’s Dinette sit a close ride away in Craryville. For a summer afternoon tipple, Roe Jan Brewing Company is up the rail trail in Hillsdale, and the creek-side beer garden atmosphere of the Lantern Inn is a somewhat stouter 25 miles down the path in the other direction.
Berkshire Bike & Board
Instagram @berkshirebikeandboard
29 State Road
Great Barrington, Massachusetts 01230
(413) 528-5555
Monday to Friday, 10 a.m. to 6 p.m.; Saturday closing at 5 p.m.
and Sunday at 4 p.m.
With Berkshire locations in Great Barrington and Pittsfield, and two other satellites in Hudson, New York and Bloomfield, Connecticut, Berkshire Bike & Board offers the gamut of cycling needs – a wide variety of gear, expert sales assistance, service and repairs, and of course, rentals.
All four locations carry an e-bike, which costs $69.99 for a single-day rate or a discounted price of 49.99 for longer rentals. The Great Barrington store also offers a non-electrified gravel bike for a single day rate of $99.99 or $79.99 for multiple days. All bookings for rentals are made online on the company’s website.
Great Barrington employee Wyatt described the gravel bike as “a little more aggressive” than a standard hybrid, and “able to handle packed dirt, a little bit of loose gravel, back roads, but not be super slow like a mountain bike” on pavement.
He said both the e-bikes and gravel bikes are well suited to handle one of his favorite routes, the Alford Loop. An approximately 20 mile ride, cyclists take Alford Road northwest out of Great Barrington, and then upon reaching Alford, may choose to take East Road to West Road or vice versa for a scenic and easy circle through the Berkshire forest and fields. In Wyatt’s words: “Great loop, super quiet, not a lot of cars.”
Natalia Zukerman
Tremaine Gallery exhibit ‘Vulnerable Earth’ explores climate change in the High Arctic.
“Vulnerable Earth,” on view through June 14 at the Tremaine Gallery at Hotchkiss, brings together artists who have traveled to one of the most remote regions on Earth and returned with work shaped by first-hand experience of a fragile, rapidly shifting planet, inviting viewers to sit with the tension between awe and loss, beauty and vulnerability.
Curated by Greg Lock, director of the Photography, Film and Related Media program at The Hotchkiss School, the exhibition centers on participants in The Arctic Circle, an expeditionary residency that sends artists and scientists into the High Arctic aboard a research vessel twice a year. The result is a show documenting their lived experience and what it means to stand in a place where climate change is not theoretical but visible, immediate and accelerating.
That shared experience — weeks spent together navigating the waters around the Svalbard Archipelago —forms the connective tissue of the exhibition. Artists work across video, photography, performance and digital media, but what binds them is proximity: to the landscape, to one another and to the evidence of environmental change.
“The residency is fantastic,” Lock said. “You fly into the most northerly airport on the planet, get on a ship with a bunch of artists and then sail around the archipelago and find a bay or a glacier, get into little rubber boats and go to shore. There are three guides with rifles … and they form a triangle around us to protect us from polar bears, and then you’re just there.”
That immediacy — of risk, of beauty, of isolation — is evident in the work on view. “Everyone is concerned with the environmental shifts that are occurring, and you’re witnessing it out there,” Lock said. “We were cleaning the beach one day and there’s so much trash on this beach in the middle of nowhere … because there’s plastic in the sea. We are witnessing these things firsthand.”
Lock’s own contributions underscore how quickly the landscape is changing. In one piece, two photographs are mounted on a glacier-shaped metal stand. “I went to photograph the glacier, and we were sailing around and because of the map, we knew we were at the glacier, but we couldn’t see it,” he said. Dense fog, created by warming air meeting cold ground, obscured what should have been unmistakable. Only later, in post-production, did the glacier emerge. “In Photoshop, I could extract the glacier, but to the naked eye, it was no longer visible.”
Other changes are even more stark. Lock recalled the reaction of the ship’s captain comparing current conditions to his charts. “His ‘up to date’ map showed that the glacier was 8 kilometers between one side and the other, but we parked at one side, sailed and moored on the other side and it was 1.4 kilometers,” Lock said. “So, it’s just like bam. It’s happening so fast.”
There is a sense of urgency in these images, but the collection also is a testament to process and to the community that forms in such extreme conditions. “There’s quite a nice network of artists who are pretty tight,” Lock said. “We were on a ship together in tight quarters for three weeks, so we got to know each other really well. And I found connections across the work with my own practice.”
Mindful of the environmental stakes embedded in the work itself, Lock made decisions aimed at reducing impact when curating the exhibition. “A lot of this work I printed with their permission to cut down on my carbon footprint,” he said.
And yet, for all its focus on fragility and loss, the Arctic exerts a pull. “It was funny, I’ve been twice,” Lock said. “When I left the last time, I was like, oh, I don’t know if I need to go back. And then I got back, and all I wanted to do was go back.”
The Tremaine Gallery is located on the Hotchkiss campus at 11 Interlaken Road, Lakeville. Gallery hours are Tuesday - Saturday, 10 a.m. to 4 p.m. and Sunday, 12 noon to 4 p.m.
Kerri-Lee Mayland
Joan Osofsky and Sharon Marston
Joan Osofsky is closing the doors on Hammertown, one of the region’s most beloved home furnishings and lifestyle destinations, after 40 years, but she is not calling it an ending.
“I put my baby to bed,” she said, describing the decision with clarity and calm. “It felt like the right time.”
At 80, Osofsky is stepping away from the business she built into an institution. Yet her attention is not fixed on what she is leaving behind but on what she calls “Beyond Hammertown,” a phase shaped not by legacy but by intention and possibility.
“Not defined by what I created, but by what I choose next,” she said.
Founded in a barn in Pine Plains in 1985, Hammertown grew into a singular brand with locations in Rhinebeck and Great Barrington, known for its warm, layered aesthetic that blended European and American antiques with rustic textures and modern simplicity. Often credited with helping to define a “modern country” sensibility, the store drew a devoted following from across the region and beyond. But for Osofsky, its success was never a solo effort.
“Hammertown was never just my story,” she said. “It was built alongside my family and colleagues, whose support and talent made everything possible.”
That sense of collaboration traces back to her earlier life as a teacher in New Jersey and Rhode Island. While raising her children in the late 1960s and ’70s, she launched a patchwork quilting business, selling work in shops in New York City and the Berkshires. She went on to work with friends on The Sweet Life Chocolate Engagement Calendar, published in the early 1980s and sold nationally, and led a PTA quilting project that still hangs in her children’s former elementary school.
Those early experiences of building a home, raising a family and creating by hand became the foundation of Hammertown. Even now, that instinct remains unchanged.
“I still love knitting for babies and making scarves for friends,” she said.
As news of the closing spread, Osofsky said she felt both the weight of the decision and the depth of the community it touched.
“I felt its weight and its love when I announced Hammertown was closing,” she said.
Still, her focus returns to what lies ahead. She describes this next phase as open, undefined and deeply personal — a shift away from building a business toward following curiosity wherever it leads. Writing, travel and creative exploration are all part of that vision, along with revisiting ideas once set aside.
Among them is a book she once considered publishing traditionally. Now, she is rethinking that path, reflecting a broader change in how she approaches creativity. No longer tied to a store or a brand but “just for the joy of it,” she said.
That shift also makes room for other parts of her life, including time with her granddaughter, cooking, learning to garden and spending time in France.
“I’ll be at Trade Secrets helping my dear friend Sharon from Marston House,” she said of the annual garden event in May benefiting Project SAGE. “She lives in France most of the year, and I visit her frequently — we shop the markets, share life and walk the French countryside. This has become an important part of my life.”
Other constants remain. Tennis, she said, has long provided not only recreation but connection. She hopes to spend more time on the court, possibly even competitively, while continuing her work with the Northeast Community Center and the Little Guild. These commitments she describes as deeply meaningful and essential to what comes next.
“That has meant a great deal to me beyond Hammertown.”
As she prepares for the transition, Osofsky speaks less about loss than about clarity — a desire for space, a readiness for quiet and the ability to move forward on her own terms. She describes this next phase as rooted in authenticity and an “imperfectly perfect life,” acknowledging that it carries both release and uncertainty.
“I’ll let go, but I’m not sure where I’m being led, and that is OK,” she said.
A year from now, she expects people might see a shift in her — someone lighter, less burdened.
“Still deeply connected to creative beauty,” she said, “just less tied to outcomes and more open to surprise.”
Though many have framed Hammertown’s closing in terms of legacy, Osofsky resists that perspective. For her, the present moment feels far more alive.
“Legacy is something you come to understand later,” she said. “Possibility is something you feel in the present.”
What she hopes people carry forward is not just a memory but a feeling of something less tangible.
“I hope people don’t just remember Hammertown,” she said. “I hope they feel it — that sense of warmth and comfort, like walking into a place that felt like home.”
She sees Beyond Hammertown not as retirement but as the beginning of something new and intentional. There is still more to try, more to learn, more to become. It just might be her most personal design yet.
“And that, more than anything,” she said, “feels right.”
Richard Feiner And Annette Stover
Amid the many cultural attractions in the region, the Barrington Stage Company in Pittsfield, Massachusetts, stands out for its award-winning productions and comprehensive educational and community-based programming. The theater’s 2026 season is one of its most ambitious; it includes two Pulitzer Prize-winning modern classics, one of the greatest theatrical farces ever written, and new works that speak directly to who we are right now as a society.
“Our 2026 season is a celebration of extraordinary storytelling in all its forms — timeless, uproarious and boldly new,” said Artistic Director Alan Paul. “This season features works that have shaped the American theater, as well as world premieres that reflect the company’s deep commitment to developing new voices and new stories. Together, these productions embody what BSC does best: entertain, challenge and connect our audiences through theater that feels both essential and alive.”
The company has several theaters within a few blocks of each other. In the Boyd-Quinson Theater, BSC’s main stage, the season features “A Chorus Line” (July 15-Aug. 8), a new 50th anniversary production of the Broadway musical that won nine Tony Awards and the Pulitzer Prize for drama. This will be followed by Michael Frayn’s beloved door-slamming comedy “Noises Off,” in a first-time BSC production directed by Gordon Greenberg.
At BSC’s Blatt Center for the Performing Arts, the St. Germain Stage season will open with “Driving Miss Daisy” (May 27-June 21), a collaboration with Palm Beach Dramaworks directed by BSC founding artistic director Julianne Boyd and starring Ray Anthony Thomas and Debra Jo Rupp. This is followed by the world premiere of “Estate Sale” (June 30-July 25) by Keelay Gipson, an Afro-surrealist artist, professor and award-winning playwright and BSC Sparks grant recipient.
The season includes other provocative and timely new works. “The Zionists: A Family Storm” (June 16-July 3), produced in association with Miami New Drama, focuses on a family gathering on a Caribbean island where old grievances give way to new political fears. “Dead Girl’s Quinceañera” (Aug. 5-29), a collective world premiere by BSC, Chicago’s Goodman Theatre and Hartford Stage, is a dark comedy about true-crime obsession, teenage bravado and what happens when girls decide to stop waiting for answers. Another world premiere, “The Urmetazoan” (Sept. 30-Oct. 25), by playwright Alex Rugman and directed by Jack Serio, tells the story of two sisters facing an imminent goodbye as one prepares to leave Earth for deep space.
“BSC is deeply committed to our home in the Berkshires, producing as many or more shows this summer than ever before, for a devoted and engaged audience,” said Managing Director Greg Reiner. “And we are continuing our deep work within this community, showing up where it matters to bring new audiences theater that matters.”
Since moving to Pittsfield in 2006, Barrington Stage has prioritized its connection to residents and families through extensive and inclusive education and community engagement programs that help make its productions accessible to all. The company strives to make BSC an artistic home for an inclusive community of talented actors, writers, designers, directors and musical directors, as well as a home for its staff, students, interns and educators.
BSC has gained attention beyond the Berkshires, with productions that have moved on to Broadway and to major regional theaters around the country. The company believes that its work to support playwrights, and their visions of the world we live in, is central to its success in creating meaningful theater that resonates with all audiences.
“BSC’s season is a thrilling reflection of who we are right now as a society, wrestling with division and longing for connection,” Paul said. “It’s an exciting season because it’s alive and designed to bring us together in the dark to experience something unforgettable.”
For tickets and more information on the 2026 season, including additional productions, concerts, cabarets and the company’s annual gala, visit barringtonstageco.org.

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Brian Gersten
Student festival directors Trey Ramirez (at the mic) and Leon Li introducing the Hotchkiss Film Festival.
The 15th annual Hotchkiss Film Festival took place Saturday, April 25, marking a milestone year for a student-driven event that continues to grow in ambition, reach and artistic scope. The festival was founded in 2012 by Hotchkiss alumnus and Emmy-nominated filmmaker Brian Ryu. Ryu served as a festival juror for this year’s installment, which showcased a selection of emerging filmmakers from around the region. The audience was treated to 17 films spanning drama, horror, comedy, documentary and experimental forms — each reflecting a distinct voice and perspective.
This year’s program was curated by student festival directors Trey Ramirez and Leon Li, working alongside faculty adviser Ann Villano. With more than 52 submissions received, the selection process was both rigorous and rewarding. The final lineup included six films from Hotchkiss students.
For Ramirez, the festival represents both a personal and creative evolution. His interest in filmmaking began with producing sports media during his freshman year, creating highlight reels for the Hotchkiss boys varsity basketball team during its 2026 NEPSAC championship season. That early work led him into photography and eventually into narrative and experimental filmmaking. Among the films screened was Ramirez’s own experimental piece, “Paradise Waits,” an abstract, montage-driven work emphasizing editing and visual rhythm.
“What I enjoy most about organizing the festival is the opportunity to curate a program that reflects a wide range of voices and styles,” Ramirez said, “while also creating a space where student filmmakers can share their work with a larger audience.”
For many filmmakers, this was the first time seeing their work projected on a large screen before a live audience, an experience Ramirez described as especially meaningful given the time and dedication behind each project.
Now in its 15th year, the Hotchkiss Film Festival continues to build on its legacy as a platform for young filmmakers. The festival not only celebrates student achievement but also signals a promising future for the next generation of storytellers.
Natalia Zukerman
‘The Laundry Room,’ a painting by Maira Kalman from the exhibition “Shaker Outpost: Design, Commerce, and Culture” at the Shaker Museum’s pop-up space in Chatham.
With “Shaker Outpost: Design, Commerce, and Culture,” opening May 2, the Shaker Museum in Chatham invites artist and writer Maira Kalman to pair her own new paintings with objects from the museum’s vast holdings, and, in the process, reintroduce the Shakers not as relic, but as a living argument for clarity, usefulness and grace.
Born in Tel Aviv, Maira Kalman is a New York–based artist and writer known for her illustrated books, wide-ranging collaborations and distinctive work spanning publishing, design and fine art.
“I always approach my work from an aspect of love,” she said. “I fall in love with a face or a chair or a shoe. And then it is my pleasure to paint. That is how I approached the pieces I chose for the installation. They spoke to me. They SANG to me.”
Her selections for the Shaker Outpost include clothing of daily life — hats, shoes, socks, gloves — alongside objects shaped by hand and necessity. A pair of bear fur mittens, a glove form, a forged iron stake. Items that once moved through ordinary days now sit in conversation with Kalman’s paintings, which draw from the museum’s photographic archive. “As I looked at the photo archive, I gravitated to images that made me happy,” she said. “The Shaker work is so full of delicate elegance and superb utility. I love that.”

The idea of utility that is elevated to poetry is at the center of the show. Kalman described the impulse to “edit your life” after encountering Shaker design, and here that instinct becomes both curatorial method and invitation. “After seeing their work, you want to run home and throw out everything you have,” she said. “You want to edit your life. You only want what is essential. The simplicity and beauty of Shaker design are rarely equaled… They have wit and wisdom. Clarity and kindness. They are practical and they sing. You just cannot go wrong.”
The exhibition also marks a return. After more than two years at the Kinderhook Knitting Mill, the museum’s programming comes back to Chatham — if only temporarily — before the opening of its future permanent home.
The pop-up exhibition at 4 Depot Square in downtown Chatham extends beyond the gallery walls. A small, carefully assembled General Store — also curated by Kalman — offers books, textiles, notecards and handmade goods by local artisans. Like the Shakers’ own public-facing shops, it blurs the line between commerce and ethos, asking what it means to buy something made with care. It is, deliberately, a place to linger.
Kalman sees the Shakers as kindred spirits. “Even though my mother was a Russian born Jew, she could have been a Shaker,” she said. “But then all of the women in my family could have been. A sense of beauty, care, simplicity and love imbued all that they did. They were frugal and fastidious.”
That inheritance feels newly relevant. “Today we have a very fast-moving day. Never enough time,” she said. “And I think that the sense of taking time to make beauty resonates very much these days. It restores the soul.”
Kalman worked closely with her son, Alex Kalman, on this exhibit. “Working with my son Alex Kalman on this installation has been a joy,” she said. “He curates for his museum MMUSEUMM, in a defunct elevator shaft on Cortland Alley in Manhattan. He is always looking for the intersection of humor and human expression and endeavor. That is how I approach the installation at the Shaker Outpost. Everything should matter.”
Shaker Outpost: Design, Commerce, and Culture runs through July 5 at 4 Depot Square in Chatham, with subsequent installations by Paula Greif and Kiki Smith later in the year. For more information, visit shakermuseum.us.
Jennifer Almquist
The Ticking Tent Spring Market returns to Spring Hill Vineyards in New Preston on May 2.
The Ticking Tent Spring Market returns to New Preston Saturday, May 2, bringing more than 60 antiques dealers, artisans and design brands to Spring Hill Vineyards for a one-day, brocante-style shopping event from 9 a.m. to 4 p.m.
Co-founders Christina Juarez and Benjamin Reynaert invite visitors to the outdoor market at 292 Bee Brook Road, where curated vendors will offer home goods, fashion, tabletop and collectible design. Guests can browse while enjoying Spring Hill Vineyards’ wines and seasonal fare.
Juarez is president of Christina Juarez & Co., a communications and business development consultancy. Reynaert is market director at ELLE DECOR, an interiors stylist and author of “The Layered Home,” which he will sign at the event.

“The Ticking Tent is about reimagining the joy of discovery — bringing together antiques dealers, artisans and design enthusiasts in a setting where community and creativity thrive,” Reynaert said.
Among returning vendors is Rhonda Eleish of Eleish Van Breems Home, with shops in New Preston, Roxbury, Westport and Nantucket. “The Ticking Tent is a fun event where you can shop curated goods, meet friends and enjoy the setting,” she said.
The market partners with ELLE DECOR as national media sponsor, along with Home & Garden CT & NY, Connecticut Cottages & Gardens, New England Home CT and Litchfield Magazine.
For information and tickets, visit thetickingtent.com or follow @thetickingtent.

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