People Cycling Rides

Western New England Greenway.

This is a Approved Ride
Ride Info
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Ride Leader
Rick Gallo
Tour Dates
Start Location
Kent, CT
End Location
Kent, CT
Cost (est.)
$1550 (USD + $100.00 ride fee)
$800 (USD
Payment Due
Avg. Distance
53 mi / 85 km
Avg. Elevation
2200 ft / 671 m
Ride Description

The Western New England Greenway was developed by the Housatonic Heritage Foundation as part of their work for the Upper Housatonic Valley National Heritage Area, a program of the National Park Service (that serves the Housatonic River watershed region) to highlight western Connecticut, Massachusetts, and Vermont (

As part of their mission, they developed a bicycle route which goes from Stamford, CT into Canada. Their route uses some primary roads, but mostly secondary and back country roads (including some hard-packed dirt). It takes one along rivers and lakes (big and small), some cities and towns (numerous quaint towns), rural areas, some bicycle trails (most paved, but a couple have hard packed surfaces) and through covered bridges.

This tour will take us pedaling in CT, MA and VT (up to the Canadian border) in a repeat of a shortened / truncated Covid impacted tour from June 2020. 

The major towns / cities / villages for our tour:

In Connecticut: Kent, Cornwall Bridge, along the Housatonic River, pass the waterfall in Falls Village.

In Massachusetts:  We pedal the entire state, south to north, through Berkshire County. From Bartholomew’s Cobble (… (Join People Cycling to read more)

Join People Cycling to read the full description, and even request to go on this ride (psst, it's free to join!)

People Cycling's Ride Rating

People Cycling has four categories for our rides – Easy, Moderate, Difficult, and Challenging. It should be somewhat obvious what these categories mean, but please become familiar with the elevations and distances that define them:

Easy rides are under 30mi/48km in average distance and 1600ft/500m in average elevation
Moderate rides are over the Easy rating but under 50mi/80km and 2460ft/750m
Difficult rides are as over the Moderate rating but under 75mi/120km and 3280/1000m
Anything over the Difficult rating

NOTE: This is not a strict guideline. There could be rides that have a day or two where the average elevation or distance exceeds the values given above. These anomalies should be outlined in the ride description. It is recommended that you read it carefully.

About People Cycling

People Cycling is a bicycle touring club, which you can join for free. We offer Domestic and International Cycling Tours which are led by volunteer Ride Leaders. Our tours are made up of a small group of participants (typically 15-20 or so) who want to ride an average of 30 to 55 miles a day over a one or two week period in interesting regions of the world. Our tours range in price from frugal getaways to luxurious adventures. We travel road, gravel, or mountain bike styles, and all bicycle types – including e-bikes, recumbents, and tandems are typically allowed.

Our ride leaders are volunteers and do not financially profit on tours they lead. They are also given broad discretion on how to lead their tours, and we consider them our greatest asset.

People Cycling tours are operated at cost or at lower cost (as negotiated by our ride leaders) than individuals can obtain on commercial tours. Within the cost of a tour, there is a nominal fee to support club operations and provide tools to ride leaders to manage their rides.

What are you waiting for? Join today to see what bicycle adventure awaits you in our club.

A lifetime membership in People Cycling is absolutely FREE, so please join us and become one of us – we the people, cycling together.