Day 1 - Hopedale to Greenfield

115.9 miles

ROUTE DETAILS: A Ride Into The Berkshires

The start of the second day marks the joining of the Team Riders and The General Class Riders.  The Team Riders will start at dawn with the General Riders heading out at 7:00am.  Riders on this stage will see an immediate change in the terrain with a couple of short but challenging climbs in Oxford.  But the real climbing comes as you hit the first series of climbs heading up to the Quabbin Reservoir.

Once the riders leave Amherst they will have the chance to grab some of the last Sprint Points on the tour along the the Northampton Bikeway.  After leaving Northampton it is a steady 15 mile climb into the foothills of the Berkshires.  This is where the riders endurance will be tested as the serious climbing starts at mile 80.  Expend to much energy early in the day and you might not have the stamina to keep up with the pack later in the day. Day 1 comes to a close as all riders roll into Shelburne Falls for the night to rest up for the final accent up Mt. Greylock the following day.

Day 2 - Greenfield to Pittsfield

62.4 miles

ROUTE DETAILS: To The Top Of Mt. Greylock!

The final day of the Tour may be the shortest in miles at 47.6 but will prove to be the most challenging for the teams due to several elements riders will have to face. The grueling topography and changes in temperatures as riders ascend from the days starting point to the summit of Mt. Greylock at 3,491 feet above sea level.

Prior to even getting to the base of the climb to the summit Teams will have to make the long arduous climb and decent along Rte 2 into North Adams.  Once arriving Teams will have little time to recover in the valley before hitting the wall that faces them at the start of the ascent.

For an average daily ride this route proves to be challenging but compound that with the two days and 250 miles of cycling prior to this stage and many of the Teams legs and spirits will be pushed to their limits. 

Pain in the Mass Tour -

Qualifying Century Ride

​109.2 miles

ROUTE DETAILS: Around the Quabbin and back...the hard way, up Mt. Wachusett.

Due to the rigors of the terrain and the limited daylight on the date of the Pain in the Mass 300 Tour, all TEAMS that wish to ride in the 3 Day tour must ride in the Qualifying Century Ride.  A predetermined start and finish time will be established to define the riders avg. speed over the course.

The riders finish time will determine if they qualify to represent that particular team in the Tour.

General Riders will be encouraged to participate in the Qualifying Century Ride as well as riders will be pulled off the course if daylight becomes a factor in the safety of the riders.​