Biking the Western New England Greenway

The Western New England Greenway. John Yuill Photos.
The Western New England Greenway. John Yuill Photos.

Biking From New York to Canada

By Andy Christian Castillo
Anyone who's been anywhere in New England knows that the landscape features some of the most beautiful scenery in the world. From vibrant trails through fall foliage toThe trail starts in New York and ends in Canada rolling, diverse forests and sweeping valleys, the northeast region of the United States is a biker's paradise.

The trail starts in New York and ends in Canada
The trail starts in New York and ends in Canada

"Biking is a great way to enjoy all of the natural beauty that Connecticut has to offer," said Brianna Lertora, a Yoga Instructor and cycling enthusiast; "Nothing beats biking past local farmland and woods, especially in the fall!"

She is one of many New Englanders who value an active lifestyle; in 2012 Health.com ranked six New England states in the top ten of the nations healthiest states – Rhode Island ranked number ten, Maine ranked ninth, Connecticut was number six, Massachusetts number four, and Vermont topped the list at number one.

Chief among all biking trails in the North East, the multi-segment, multi-state Western New England Greenway connects New York City and Montreal with a continuous network of bike trails. A recent release posted on Bike Walk Connecticut, said that "the aim is to enhance sustainable transportation and recreation opportunities by linking the communities along the route."

Volunteer Driven

The entire project is volunteer driven, and follows Route 7 through the very western portions of Connecticut, Massachusetts and Vermont. The route, which traverses over 300 miles of mapped trail, connects with the Merritt Parkway near Norwalk, CT and ends at Quebec's Route Verte.

"Ultimately, we'd like to see as much dedicated bikeway as possible," said Dan Bolognani Executive Director of the Upper Housatonic Valley National Heritage Area. "We'd like to see more, or all of the Greenway to be either rail beds, or dedicated bikeway. Right now, maybe 10% is dedicated bikeway." He went on to say that the rest of the route is over roads.

According to a press release, "Since 2010 a group of volunteers from the three New England states have been working to coordinate an annual conference, create a website / Facebook site, and to map and publish the most favorable on-and-off-road route."

The project started with the Houbike Trail, a 35-mile route through the Housatonic River Valley.

"In the course of working that local piece, we realized that immediately to the north and south of our area, we had local bike groups working on similar projects," said Bolognani, "so we got in touch with others and started talking with them. There are now 11 organizations working on the freeway, all with a common goal, to create a route from Long Island Sound to Montreal."

The WNEG winds through a rich tapestry of picturesque New England towns, and takes travelers to locations they might otherwise miss – here are just a few:

Bikers head out on the annual ride down the Western New England Greenway
Bikers head out on the annual ride down the Western New England Greenway

1. Danbury, CT
About an hour away from Manhattan by train, with a population over 80,000, Danbury is within the New York metropolitan area. The city has a rich history, and a heritage that has carried over into the modern era; there are a plethora of things to see, like the Danbury Rail Museum, Military Museum of Southern New England and Tarrywile Park & Mansion.

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2. Norwalk, CT
Norwalk is also in the New York metropolitan area, and is the sixth largest city in Connecticut. It's a thriving coastal city with deep roots that go back to Colonial days. While you're there, stop by the South Norwalk Historic District, or spend the day at The Maritime Aquarium; check out the many museums, or take the ferry to Sheffield Island and explore the trail system and lighthouse.

3. Pittsfield, MA
Tucked into a beautiful natural landscape of the Berkshires, Pittsfield was home to the great American author Herman Melville during his most productive writing years – his home, Arrowhead, which is registered with the National Historic Landmark and National Register of Historic Places, is open to tours. A few other places to check out, are the Colonial Theatre, which was built in 1903 and offers year round entertainment, and Mass Audobon's Canoe Meadows Wildlife Sanctuary – a 253-acre sanctuary that includes hiking trails, along the Housatonic River.

Stop in at the many historic and cultural sites along the way
Stop in at the many historic and cultural sites along the way

4. Lenox, MA
Another beautiful, quiet town in the Berkshires, Lenox is Tanglewood/Boston Symphony Orchestra's summer home; each season offers diverse concerts in a broad range of musical forms and styles. After the show, tour the Frelinghuysen Morris House & Studio and see the abstract artwork of George Morris and Suzy Frelinghuysen, or go to The Mount: Edith Wharton's Home, and see where author Edith Wharton penned The Age of Innocence. Lenox is also the home to the famed Jacobs Pillow Dance Company, with performances every summer.

5. Stockbridge, MA
Not far from Lenox, Stockbridge is one of the most beautiful towns in New England; with a quiet downtown set in a breathtaking landscape, there's a lot to see and do in the city: browse the Berkshire Botanical Garden, or paruse through the Norman Rockwell Museum.

6. Great Barrington, MA
Another absolute gem of a city, Great Barrington is a haven of quiant local shops and out-of-the-way eateries. It's an artistic treasure trove; the boyhood homesite of W.E.B. DuBois, and the birthplace of one of the oldest surviving theaters in the country – Mahaiwe Performing Arts Center. You'll notice lots of cars with New York state plates here, and the restaurants offer these summer and weekend residents plenty of tasty dining options.

7. Manchester, VT
According to the Western New England Greenway's website, "the American Museum of Fly Fishing has the worlds largest collection of angling-related items (rods, reels, flies, tackle, art, and books) and exhibits document the evolution of fly fishing as a sport, art form, craft, and industry, dating back to the 16th century. The Southern Vermont Arts Center (which has almost 800 pieces of 19th and 20th century art pieces) and a classic Vermont landscape, make Manchester a great place to stop and take a break. Manchester is the home of Orvis, where you can cast into their trout-stocked pond and pick up some clothing, camping gear or a top-notch flyrod.

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8. Bennington, VT
Few covered bridges remain in service – and two of them are in Bennington. Located in postcard-esque Vermont, one of the finest and best preserved Victorian Mansions in New England is close by, and a monument commemorates the Battle of Bennington – a battle that was instrumental in the outcome of the Revolutionary War.

9. North Adams, MA
This list wouldn't be complete without including Mass MoCA – or the Massachusetts Museum of Contemporary Art. The center is one of the largest centers for contemporary visual and performing arts in the United States. And as big as it is, it's now being renovated to be twice its current size! Mass Moca is where the Chicago rock band Wilco holds their annual Solid Sound festival in early summer, and where Fresh Grass celebrates bluegrass every September.

Also in North Adams, the Western Gateway Heritage State Park & Museum commemorates the construction of the Hoosac Tunnel – a monumental feat of engineering during the 19th century.

10. Addison, VT
A French fort sits near the shores of Lake Champlain – built to prevent the advancement of British forces during Colonial America. The D.A.R. State Park provides a great place for camping and picnics, to break up the ride.

11. Shelburne, VT
Often, Shelburne is overshadowed by it's sister city, Burlington – but don't miss out on great places like Shelburne Farms, which has rolling hills and a farmhouse with a Hogwarts type courtyard, where you can pet animals and eat homemade cookies. On the ride home, stop by Shelburne Museum a fantastic collection of transplanted historic buildings, or check out Vermont Teddybear.

"The trail typically takes about six days to complete," said Bolognani, "And there are dozens and dozens of places to stop and enjoy along the route. Eventually, we'd like to include all of the services (in a brochure, and website), like lodging, parkways, and heritage sites, so that it's more than just biking – we'd like to include cultural and historical sites, like the Danbury Railway Museum, the Eric Sloan Museum and the Kent Falls State Park."

Ride a bike from New York to Montreal across some of the finest countryside in the US. Read about the Western New England bikeway.
Ride a bike from New York to Montreal across some of the finest countryside in the US. Read about the Western New England bikeway.
Andy Christian

During a deployment as a firefighter with the USAF to the sweltering Middle East, Andy was bitten by the travel bug and smitten with the allure of adventure. Since then, he’s traveled everywhere; and when he isn’t on the road, he’s dreaming of far away places.

A 2016 graduate of the University of Massachusetts Amherst he’s now at Bay Path University studying an MFA in Creative Non Fiction, and works as a beat reporter at a small daily newspaper. Andy lives in S. Deerfield Mass.