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 millertonnews.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.”
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/.