By Jonathan O'Keeffe
Published 10/13/2012; Updated 09/15/2021

by Jonathan O’Keeffe » Sun Oct 14, 2012 5:02 pm

It felt like we skipped fall and went straight to winter on Saturday, with temperatures below freezing at the start. Apart from the cold, though, it was a beautiful day, and the low temperatures didn’t deter the hardy group of six that showed up at the start — Roberto, Tim, Bryant, Frank, Joe, and myself.

We rode out to Williamsburg, and then took a series of back roads (Village Hill, Old Goshen, and East Street) up into Goshen. This is a nice series of climbs which avoids the traffic on Route 9, with some good scenery and a bit of dirt along the way. From Goshen we had a fast and cold descent westward into the wind on Route 9, stopping to warm up at the Olde Creamery in Cummington. A big climb south on Route 112 leads up into Worthington, and then on to Trouble Street, a road I’ve been wanting to check out since I found it on a map last year.

Trouble Street is indeed troubling, with a pretty good climb initially before it turns to dirt, followed by a fairly steep descent, and then another climb which leads up to Route 143. 143 descends for a bit, and then rolls upward for a big long climb up to the windswept highlands of central Peru (the highest town center in Massachusetts, at about 2,100′). We cut south on South Road to pick up the northwestern end of the Skyline Trail and headed south through Middlefield. The Trail mostly descends in this direction, but packs a few good rolling climbs along the way. Approaching Huntington, the Trail drops rapidly as it approaches the Westfield River, and it was on the steepest section, rolling along at 40+ mph, that we came around a bend to find a large porcupine slowly crossing the road directly in front of us. We scattered, somehow managing to avoid both the porcupine and the oncoming traffic, and then rolled down the rest of the descent with elevated heartrates and residual adreneline.

We stopped at the general store in Huntington to refuel, and then headed up the last big climb of the day, slogging up County Road to the high point of Route 66. From there it was all downhill back to Northampton, where we arrived around 2PM with tired legs. My computer said it was around 70 miles @ 16.3 mph, with around 6,500′ of climbing.