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.”
Lakeville Journal
NORFOLK — Sally Sterling Ellis Quale, of Norfolk, Connecticut and St. Petersburg, Florida, formerly of Bronxville, New York, died unexpectedly of heart failure on July 7 at the age of 87.
Sally will be remembered for her deep commitment to her family and communities and for her warmth, kindness, intelligence, creativity …and, of course, for her beautiful smile and deliciously sweet sense of humor. She was a gentle leader, contributing her talents as a teacher, writer, musician, athlete and organizer.
Born in Chestnut Hill, Philadelphia, to Addison Sterling Ellis and Marion Mullison Ellis, Sally was the eldest of three sisters. She graduated from Springside Academy and Smith College, where she was a student leader and an All-American in both lacrosse and field hockey. Devoted to Springside throughout her life, she served on its Board of Trustees and received its Distinguished Service Award for leadership, including establishing an American chestnut arboretum---the restoration of the American chestnut being a lifetime interest of Sally.
Sally began her career as a teacher at The Park School in Brookline, Massachusetts, where she quickly became head of the middle school. Her love of books and writing then led her to New York publishing, where she worked at Random House, Alfred A. Knopf, and Viking Penguin. She continued her active athletic life, playing tennis, co-ed softball and soccer in the publishers’ league in Central Park, and even skiing Tuckerman’s Ravine on Mount Washington.
A gifted pianist, organist and singer, Sally performed with New York’s Blue Hill Troupe, where she met and married the love of her life, Drew Quale. Soon two spirited sons, Andrew III and Addison, arrived and the family moved to Bronxville, New York.
Together they built a life centered on family, community, education, music and sports. She founded the Bronxville Bulletin, became the Bronxville School’s first Public Information Officer, served as Project Director for the publication of the school’s history and produced six Blue Hill Troupe performances to benefit the Bronxville School Foundation, which she and Drew were instrumental in establishing. She directed and accompanied the Bronxville Hilltop band and singers at the Hilltop’s annual Holiday Party. She encouraged many NYC friends to move to Bronxville, who themselves contributed greatly to Bronxville’s educational and musical life.
In 1984, Sally and Drew purchased a 1780 farmhouse in Norfolk, Connecticut as their “casa de campo,” beginning a decades-long love affair with Norfolk, Doolittle Lake and the entire Northwest Corner. In Norfolk, she helped found the town newspaper, Norfolk Now, organized many concerts and cabarets, and produced several Blue Hill Troupe productions for the pre-season opening benefit of the Norfolk Chamber Music Festival. In recent years, Sally and Drew also found a welcoming winter home and deeply caring friends at Westminster Shores in St. Petersburg, Florida.
Sally is survived by her husband, Andrew Christopher Quale Jr.; her sons, Andrew Christopher Quale III and Addison Sterling Ellis Quale; her daughter-in-law, Nágila Pereira Quale; her grandchildren, Strynden Pereira Quale, Amattan Pereira Quale, and Hannah Zeilyn Pereira Quale; her sister, Mimi Garrett; Andrew’s partner, Jessica Euphamie Moore; and many nieces, nephews, extended family members and friends.
Two Memorial Services will be held: Saturday, August 22, 11 AM, at United Church of Christ Congregational, 12 Litchfield Road, Norfolk CT 06058; and Saturday, October 10, 11 AM at Reformed Church of Bronxville, 180 Pondfield Road, Bronxville, NY 10708.
Lakeville Journal
KENT — Dorothy McEnroe Casey, 93, a longtime resident of Kent, Connecticut, passed away peacefully on Thursday, July 23, 2026, at New Milford Hospital in New Milford. Born on July 28, 1932 in Sharon, she was the daughter of the late Leo McEnroe, Sr. and Dorothy Belter McEnroe.
Mrs. Casey was a graduate of Amenia High School and a homemaker. On Dec. 1, 1951, at Immaculate Conception Church in Amenia, New York, she married John Finn Casey who died on April 17, 2006.
She was a longtime parishioner of Sacred Heart Church in Kent.
Mrs. Casey is survived by three daughters, Kathleen (Katie) Casey Moore, and her husband, Jonathan, of Kent, Connecticut; Margaret (Meg) McEnroe Casey, of Milwaukee, Wisconsin and Jacqueline (Jackie) Casey McGuinness, and her husband, Michael, of Fairfield, Connecticut and two brothers, Joseph McEnroe of Amenia, New York and James McEnroe of Burlington Flats, New York. She is also survived by six grandchildren, Andrew Casey Moore, and his wife, Kristen; Christopher Sizer Moore; John Finn McFadyen; Margaret Casey McGuinness; Caroline Grace McGuinness and Patrick Edward McGuinness and a great grandson, Aiden Casey Moore.
Besides her parents and husband, she was predeceased by a brother, Leo McEnroe, Jr. and a sister, Margaret Wilcox.
There will be no calling hours. A Mass of Christian Burial will be held at 10 a.m. on Wednesday, Aug. 5, 2026, at St. Kateri Tekakwitha-Sacred Heart Church, 17 Bridge St., Kent, CT. Burial will follow at Sacred Heart Cemetery, Kent, CT. Memorial contributions may be made to the Kent Volunteer Ambulance, 28 Maple St., Kent, CT 06757.
Lakeville Journal
MILLERTON — Louise R. Black, 86, born July 16, 1939, in Queens, New York, died on July 15, 2026, with her partner of 26 years, Mary Howard, by her side. She is also survived by her nephews David Black and Jason Black, and his wife, Kerri; and niece Tiffany Black and her husband, Shlomo Toledano.
After graduating from the University of North Carolina Women’s College and earning two master’s degrees, Louise taught physical education for 35 years at Scarsdale (NY) High School, chairing the department and serving as the first woman Athletic Director. An accomplished fencer, tennis player, and swimmer, Louise’s enduring fondness for sports included a love of the Brooklyn Dodgers, though she never quite recovered from their move to the West Coast.
Louise’s artistic talents came through in her knitting, her painting, and her gardens. A master knitter, for many years she and Mary hosted a weekly knitting group at their home. She was recognized for her Japanese watercolors and landscapes; her passion for flowers was expressed in the abundant roses bordering her property.
An avid traveler, she also found great joy spending summers at her family camp on an island in the Hudson River. Cars and jazz were perennial fascinations, and Doris Day was a favorite.
Louise dedicated much of her life to community service, first as an enthusiastic volunteer at Habitat for Humanity in Westchester County. Following retirement, she moved to Millerton, New York, and was soon immersed in the local library, developing a finders’ guide for the North East Historical Society; and the co-founding of Comida de Vida food pantry at St. Thomas EpiscopalChurch in Amenia, New York.
In lieu of flowers, please consider donating to Food of Life / Comida de Vida Food Pantry St. Thomas Episcopal Church, 40 Leedsville Road, Amenia, NY 12501 (845) 373-9161 www.stthomasamenia.com or Habitat for Humanity: https://www.habitat.org/support
A celebration of Louise’s life will take place on Thursday, July 30, 2026 from 2pm to 4pm at the Scott D. Conklin Funeral Home, 37 Park Avenue, Millerton, NY 12546. To send an online condolence to the family, please visit www.conklinfuneralhome.com

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Lakeville Journal
MILLERTON — Mary Simmons, 96, a fifty‑six‑year resident of Millerton, New York, and formerly a lifelong native of College Point, Queens, New York, died peacefully on July 26, 2026, at her daughter’s home in Sharon, Connecticut. Mary devoted her life to her family; to know her was to love her.
Born July 15, 1930, in College Point, Queens, New York, she was the daughter of the late Anthony and Sarah (Longo) Marano. On Oct. 26, 1952, in College Point, New York, she married Ray Daniel Simmons II. Their marriage lasted nearly sixty‑two years; Ray passed away on April 24, 2013. Mary was a longtime parishioner of St. Patrick’s and Immaculate Conception Churches, where she belonged to the Rosary Altar Society. For many years, she enjoyed spending winters in Florida with family and friends. Mary was famous for her Sunday macaroni dinners, which she lovingly prepared for her family and many dear friends throughout the years. All were welcomed, and it was always a packed house. Her greatest joy was spending time with her siblings, children, grandchildren, great‑grandchildren, and her large extended family. She will be deeply missed by all.
Mary is survived by her children; Ray D. Simmons III of Millerton; Maureen Chodan and her husband Jimmy of Florida; Robert A. Simmons and his wife Dara of Amenia Union; Ralph J. Simmons and his husband James Segrue of Spain; Mary Ellen Simmons of Vermont; Roseann Roux and her husband Brian of Sharon, and Louis A. Simmons of Millerton. She is also survived by many grandchildren, great‑grandchildren, and several nieces and nephews. In addition to her parents and husband, she was predeceased by seven siblings and several dear friends and extended family members.
Calling hours will be held on Friday, July 31, 2026, from 1 p.m. to 5 p.m. at the Scott D. Conklin Funeral Home, 37 Park Avenue, Millerton, NY 12546. A Mass of Christian Burial will take place on Saturday, August 1, 2026, at 10 a.m. at St. Kateri Tekakwitha Parish, St. Bernard Church, 52 New Street, Sharon, CT. Rev. Gregory Jaworowski officiating. Interment will follow at St. Patrick’s Church Graveyard at the corner of Barton and Church Streets in Millerton, NY. Memorial contributions may be made to the Millerton Fire Company, P.O. Box 733, Millerton, NY 12546. To send an online condolence to the family, flowers to the service, or to plant a tree in Mary’s honor, please visit www.conklinfuneralhome.com.
Lakeville Journal
STANFORDVILLE —Margaret Anita Layton passed away on April 30, 2026, after a recurring battle with cancer, surrounded by friends and loved ones. She was predeceased by her parents, Anita and Jack Egan, brother John P. Egan, III, and nephew Michael Egan. She leaves behind a brother, numerous nieces and a nephew, as well as a community of chosen sisters who loved her very much.
Margaret was born in the Bronx, New York, and moved to Clinton Corners as a small child. Margaret spent her adult life in Stanfordville, where she owned Margaret A. Layton, E.A. Tax and Business Consulting. Margaret was a lover of all animals and an avid horse enthusiast with an active presence in the draft horse community. Midge lived out loud. Her vibrancy left a mark that will never be forgotten and will be sorely missed.
A private burial will take place at Friends Upton Lake Cemetery in Clinton Corners, New York.
Memorial donations may be made to Dutchess County SPCA, 636 Violet Ave., Hyde Park, NY 12538. Arrangements have been entrusted to Scott D. Conklin Funeral Home, 37 Park Avenue, Millerton, NY 12546.
To send an online condolence to the family or to plant a tree in Midge’s memory, please visit www.conklinfuneralhome.com
Lakeville Journal

Join The Lakeville Journal for a community celebration, featuring local nonprofits and businesses, festive family fun, great food, and engaging activities.
Danny Tieger | 11am - 12pm
John Keilty/Johnny Rox | 1-3pm
Face Painting
Scavenger Hunt
Balloon Animals
21st Century Fund for HVRHS
Berkshire Taconic Community Foundation
Community Health & Wellness Center
Congregational Church of Salisbury, UCC
The Corner Food Pantry
Crescendo
Housatonic Child Care Center
Noble Horizons
Nuvance Health (Sharon Hospital)
Project SAGE
NW Connecticut Community Foundation (Women & Girls Fund)
Salisbury Association
Salisbury Affordable Housing Commission
Salisbury Housing Committee
Salisbury Housing Trust
The Salisbury Forum
Western Connecticut Area Agency on Aging
Cousins Maine Lobster food truck
The Taco Shack
LaBonnes’ Market
Provisions at The White Hart
Sweet William’s
See you at the Lakeville Journal Street Fair!
If you have any questions, please email streetfair@lakevillejournal.com


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