Organized Rides

A number of fun, challenging, and well-supported group rides and races take place in and around our area. From week-long tours to intense hillclimb time trials, there’s an event for everyone.


Downtown Bike Around

All are welcome for a fun community ride around downtown North Adams.  Meet at 6:30PM each Thursday this summer (2017) at the St. Anthony’s Drive city parking lot, and join a group of riders from 3-83 (really!) to enjoy a slow and flat ride through the city.  This group has a great time promoting cycling in North Adams!


Pittsfield Mountain Bike Training Series 

Pittsfield State Forest contains well-maintained trails that are ideal for beginner through advanced mountain bikers. This summer, the Berkshire Cycling Association sponsored a free training program for beginner mountain bikers. Go to for more info.


Adams Pedal N’ Plod 

The town of Adams hosts the annual Pedal N’ Plod race every summer. Partners can team up to split the 4-mile run and 22-mile bike legs of the race, or an individual can enter as an “iron person” and complete both legs solo. This race is ideal for friends and family to challenge each other in a competitive environment at a great value (pre-registration is only $40 per team and $30 for an individual entry).

2017 race coverage by the Berkshire Eagle:
Press ReleasePhotos 

HOORWA River Ride

Held by the Hoosic River Waterrshed Association, the 13th Annual Hoosic River Ride will be held on August 12, 2017. A full-day event, complete with a delicious breakfast beforehand and picnic afterwards, contains rides with lengths varying from a family-friendly 7-mile ride to a full century ride.

You can find a detailed map of the Hoosic River Watershed area, which includes much of North Berkshire county, here.


NCC Mt. Greylock Hillclimb Time Trial

Distance: 9.3mi

Elevation Gain: 2,704 ft.

Description: Hosted by the Northampton Cycling Club, the Mt. Greylock Time Trial is exactly what it sounds like: a race to the top of the tallest peak in MA. While you can ascend at whatever pace you’re comfortable with, there’s really no easy way up Greylock. This event is well-run by a number of enthusiastic volunteers, and you can register here.

View Photos from the 2016 Mount Greylock Hillclimb here.

BCA Mount Greylock Century Ride

The Berkshire Cycling Association holds the Mt. Greylock Century every Summer. As not only the biggest and baddest century in North Berkshire County- over 10,000 ft. of elevation gain, including climbing the tallest peak in the state – it certainly offers the most bang for your buck. A pre-registered entry fee of a mere $45 grants you access to coffee and bagels in the morning before the race, and fully-stocked aid stations to replenish with throughout the ride.

Mount Greylock Century home page

Berkshires to Boston Tour 

The Berkshires to Boston Bicycle Tour is a four-day, 240 mile bike tour crossing Massachusetts from the New York border to downtown Boston. Showcasing the best of Massachusetts cycling, the tour begins in the scenic Berkshire hills, meanders through the Connecticut River Valley, rolls over the state’s central plateau and spins through Lexington and other historic communities before arriving in the vibrant capital – Boston. There, riders join more than 5,000 cycling enthusiasts for TD Bank Hub on Wheels, Boston’s annual bicycling festival.

Read more about the tour/register here: 


The Western New England Greenway – A Heritage Bikeway – Heritage Ride

The Western New England Greenway (WNEG) is a bicycle route in progress, connecting the East Coast Greenway at Norwalk to the Route Verte in Quebec Province, Canada.  The WNEG concept really came into being at a conference held in November 2011 at Bennington, VT attended by different bicycle organizations working on trail development and bicycle routes in western CT, MA and VT. Riders gather casually for an 8-day tour from Wilton, CT to Montreal that passes through the Berkshires.

2016 Route Details

2016 Berkshire Eagle coverage 


Overland Camps


Overland offers adventurous summer experiences worldwide for 4th to 12th graders.  Far more than simply a summer experience, Overland is a life experience with value and resonance that extends beyond the boundaries of a single summer. In everything we do, we seek to inspire our students to see how beautiful and exciting, how full of promise the world is.