A bridge on the Farmington Canal Trail

Route Canal

Ah, the poor Farmington Canal—it never stood a chance.

Construction on the waterway began in 1825 in an effort to improve transport throughout central Connecticut and into Massachusetts. The canal’s financiers hoped that the route, which officially opened in 1835 and stretched from New Haven to Northampton, Massachusetts, might be as prosperous as the bustling Erie Canal in New York. However, by then, railroad transport had improved greatly, making the canal financially unfeasible. In 1848, the canal was abandoned altogether and the New Haven and Northampton Company laid down a rail-bed beside it.

Goodbye, boats. Hello, locomotives!

From there, the rail line had many owners, from the New York, New Haven and Hartford Railroad Company in 1887 to Guilford Transportation Industries (now known as Pan Am Systems) in 1980 and many others in-between. Guilford Transportation had difficulty sustaining the route mostly due to irreparable flood damage, and by 1985, it was shuttered altogether and added to the National Register of Historic Places.

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But the land along the tracks was given one last shot-in-the-arm in 1991, thanks to the Intermodal Surface Transportation Efficiency Act. This act of Congress allowed the Connecticut Department of Transportation to access federal funds to convert the defunct tracks into a multi-use asphalt path along the same route, roughly, as the original canal.

Thus the Farmington Canal Heritage Trail was born. The trail is a smoothly paved two-lane path with plenty of room for cyclists, power-walkers and stroller-pushers. Rollerbladers are welcome, too, but does anyone actually rollerblade anymore?

Today, the Connecticut section of the trail is 70% complete with multiple points of entry between New Haven and Simsbury. In Massachusetts, the trail is about half-finished, with a terminus at the Northampton Rail-Trail. Plans are underway to complete the entire route, though there is no concrete timetable for doing so.

It’s both relaxing and invigorating to cycle up the trail to the edge of New Haven for a breezy glide north toward Hamden and Cheshire. To access the beginning of the trail, head to the intersection of Canal Street and Gregory Street in New Haven’s Dixwell neighborhood, not far from downtown. A small, wooden post marks the entryway. Urban landscapes dominate the beginning of the trail as it winds through historic Newhallville and into Hamden. There you’ll ride beside Dixwell Avenue, and if you’re lucky, you might hear powerful gospel music streaming from one of the myriad churches that sit along the trail’s edges. It’s also an excellent alternative route to The Space at 295 Treadwell Avenue in Hamden if you’re looking to catch a show.

Further along, the trail opens up as it runs parallel to Whitney Avenue. Sleeping Giant and Quinnipiac University come into view nearby Lock 13, one of two original canal locks still visible today. The other, Lock 12 in Cheshire, is still well-maintained and even has a functioning lock-house, which serves as a canal museum. It’s open to the public the first Sunday of every month.

The trail currently comes to a halt in Cheshire, as that section is still in the design phase. But things don’t have to end there. If you’re feeling ambitious enough to attempt the entire 84-mile route from New Haven to Northampton, you can do so with some careful planning and a decent map, which you can obtain by contacting the kind folks of the Farmington Canal Rail to Trail Association.

After winding through the quiet, friendly neighborhoods of Cheshire and Southington, the trail picks back up a little past Plainville and heads toward Avon. The ride through these streets is hilly and taxing but well worth pushing through to witness the fantastic scenery ahead. In Simsbury, the trail affords arrestingly serene views of farmland including fields of Connecticut shade-tobacco. That’s right: we grow tobacco in the Nutmeg State, some 2,000 acres of the stuff all along the Farmington River Valley. The leaves grown here are used to wrap cigars and are considered some of the finest wrappers in the world, according to Cigar Aficionado Magazine. The trail follows these fields for miles.

After crossing the Massachusetts border, take a break at Red Robin Hood’s Barn, a lunch and ice cream spot with ample bike racks and a rocking chair-laden porch on which to rest and people-watch. The kitchen will even fill up your water bottle if you ask nicely enough. The trail continues here through Westfield, MA, and on to downtown Northampton where there’s plenty of affordable lodging and excellent restaurants.

End to end, dedicated riders can complete the journey in just under 10 hours. It isn’t easy, especially through hilly Southington, but it’s well worth it. Along with excellent exercise and lush scenery, the journey offers a nice lesson in Connecticut’s past and present.

Though both the canal and railroad iterations of the Farmington Canal Heritage Trail ultimately failed, this latest version seems likely to last. There are no private financiers looking for big returns. No one is making risky bets on any particular transport technology of the moment.

Instead it’s a monument to civic cooperation and engagement—just a trail, yes, but one teeming with good intentions, small surprises and simple pleasures.

Written and photographed by Jake Goldman.

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