By Jonathan O'Keeffe
Published 11/09/2013; Updated 09/21/2021

by Jonathan O’Keeffe » Sat Nov 09, 2013 8:06 pm

Our first real cold-weather ride of the fall, with the temperature sitting at 34° at the start, and staying below that most of the day. Nevertheless, a surprisingly large group of 18 showed up to challenge the weather. Tim laid out another outstanding route for us, targeting some back roads and dirt roads in Cummington and Plainfield that we haven’t seen before, with some great scenery and quite a lot of climbing.

We started by heading out Route 66 to Outlook Farm, and then turned north through Westhampton towards King’s Highway and Reservoir Road. Northwest Rd took us past the Krug Sugarbush into Chesterfield, where we stopped to refuel, warm up a bit, and scarf down some of their chocolate-chip-cookie whoopie pies. It was tough to leave the warmth to face the freezing descent down into Chesterfield Gorge.

From the gorge, we followed Fairgrounds Road north into Cummington, crossing Route 9 and heading further north on Plainfield Road. We turned off on Pleasant St, which started a great stretch of quiet back roads and well-surfaced dirt roads. On Pleasant St we were immediately confronted with a flock of goats giving us the stink-eye from the edge of the pavement, and later passed some long-horned cattle that seemed determined to sprint alongside us as we rolled along.

We successfully avoided the wildlife and made our way back down and across Route 9, picking up Loomis Road heading south, which has a great steep paved climb initially, and then turns into a nice dirt surface climbing a fair bit higher. We took Sugar Hill Road down to Route 143, and then did the big descent from Bofat Hill down to Spring Street. People had been dropping off here and there along the way, and we were down to a crew of five as we rolled back to the slightly warmer temperatures back in Northampton.

Altogether I had about 53 miles at 15.4 mph, with about 6,000′ of climbing.