By Jonathan O'Keeffe
Published 12/10/2011; Updated 11/25/2021

by Jonathan O’Keeffe » Sat Dec 10, 2011 11:09 pm
Our run of great late-fall cycling weather continued into the second weekend of December, with temperatures around freezing at the start, but the bright sunshine and an initial lack of wind made it feel a bit warmer. We rolled from the Academy with Jonathan B, Mike Y, Chris, Rich, Ron, Roberto, Frank, and me. I’ve been trying to keep us out of the hilltowns the last couple weeks, after a couple of somewhat-treacherous snowy passages through the D.A.R. State Forest in Goshen a few weeks ago. So we started today by following the standard northbound route along the river up River Road, into the teeth of a strengthing wind blowing from the north and west.

Roberto and I, sitting at the back of the pack, conspired to try to challenge Chris for the Deerfield town line at the end of River Road. We sat back behind a gap, and then attacked from the back, with Roberto leading me out. We blew past Chris in the lead group and opened a big gap, but we knew he would respond right away. Unfortunately, we launched way too early, leading to a dual breakaway off the front that neither Roberto nor I could sustain. After about a week and a half, Chris tracked us down and blew by me to easily take the win. The best laid plans…

After the initial flat section, we moved into the main section of the ride, which I had conceived as a tour of the Pocumtuck Range, the ridgeline of trap-rock hills stretching northward from Sugarloaf into Greenfield. I planned the ride as a circumnavigation of the range, punctuated by climbs into the heights where possible.

Chris and Rich turned off at the Sunderland bridge, and the rest of us kicked off the tour with a climb of Sugarloaf, the southern anchor of the range. The park was closed to automobile traffic, which made for a nicer climb, although there were quite a few pedestrians, and big piles of leaves on the road on some of the curves. Ron and Roberto and Frank were pushing a fast pace in the front of the group, while Jonathan decided this would be a good time to hammer me into the ground. He dropped me in the initial steep section; I caught up on the flatter portions midway, and then he found another gear and accelerated on the final steep sections at the top, finishing about a minute ahead of me — great climb!

We descended Sugarloaf and headed further north on River Road for a mile or so before turning left on Hillside Road, which cuts across a col in the middle of the range to traverse from River Road on the east side of the range to Routes 5 and 10 on the west side, with a pretty big climb and some great views to the west along the way. We hit Rt. 5/10 and headed further north, with the wind blowing harder in our faces, and Ron pulling us most of the way. Approaching Greenfield, we took a right turn on Keets Road for a nice climb back up to the top of the ridgeline at Woolman Hill, our third big climb of the day.

Woolman Hill has no outlet, so we we had to retrace our steps back down the hill before heading further north into Greenfield, where I’m pretty sure the normally-proper Jonathan uttered an obscenity as we turned left onto Mountain Road to begin our fourth (and last) big climb of the day up to Poet’s Seat at the northern terminus of the Pocumtuck Range. After a closed gate near the top, there’s a narrow paved road leading up to the tower at the summit, where we enjoyed a very scenic vista overlooking Greenfield, in the face of a stiff and cold wind.

We descended, and had a pit stop, before continuing towards home southward on River Road, where Roberto and I somehow ended up in a two-man breakaway off the front, pushing very hard all the way to 116, where we regrouped. We crossed the river at that point, heading south on Rt. 47, and ended up fighting a crosswind that was now coming from the west.

Roberto and I turned off on Rocky Hill Road to head back to Amherst, while the rest of the group headed back to Northampton. At the split, I had 49.8 miles @ 16.9 mph, 3,200 feet of climbing. 34° at my house at the start, 38° at the finish.

It’s only a matter of time before the weather gets worse, but as long as things stay dry with temperatures in the 30’s, we’re going to continue the Saturday rides as long as we can, so keep an eye on the calendar page for next weekend (and beyond). We’ll have updates there on Friday afternoon and Saturday morning with the current status for the ride.


by Chris deHahn » Sun Dec 11, 2011 5:10 pm
Jonathan O, Mike Y and I were having a nice pleasant little conversation on the front pulling the group into the wind when you and Roberto blew by like a pair of F-15’s. I wasn’t going to even try and catch you, but one of you looked back, so I put it into kilo mode for what seemed like 2+ kilos which just killed me at this time of year. I only beat you by half a wheel. A very impressive effort by the two of you.

Jonathan B, nice job on Sugarloaf!!!

by admin » Sun Dec 11, 2011 9:02 pm
Wow – I had not realized it was a town line conspiracy

Great ride, route, and group as usual – next Saturday’s forecast looks good again but it is still far out


by jonathanbrody » Sun Dec 11, 2011 10:04 pm
Thanks for the compliments. Great route Jonathan. And thanks to Ron who is simply a steam engine on two wheels. He is an athletic site to behold. Hope to see you-all on the years ride. Happy holidays!

by Frank Sleegers » Mon Dec 12, 2011 1:04 am
Was a great ride. Wow I should buy a thermometer…Had to shower me warm.
Great seeing you all again before the break.
Thanks Jonathan for your great report.
I wish everybody a great Chrismas.


by Roberto Ludovico » Mon Dec 12, 2011 8:14 am
Wonderful ride indeed, with a great group still eager to have fun on SMRs despite the mid-December temperatures. Let us hope for dry roads until next Saturday still.
Chris, the failure of the attack plan that Jonathan and I put together hoping to take at least one town line away from you demonstrates once more how strong you are riding this year. Great job!

On a slightly different note, I think I can voice the SMR group’s gratitude to Jonathan B. for organizing this ride, and to Jonathan O. for plotting out fantastic routs every week, both challenging and fun. I thought that I had seen most of the Pioneer Vally and Hill Towns’ roads by now, but the fact that I am still riding on new roads every week is quite impressive. I am sure that this involves a considerable time investment on Jonathan’s part.
Thank you both for a splendid season of SMRs. I am sure I am not the only one looking forward to spring to re-do it all over again. ‘Till then, be well.


by Jonathan O’Keeffe » Mon Dec 12, 2011 8:42 am
Thanks, Roberto and all. I appreciate the feedback, and really enjoy riding with you guys every week.