By Tim Cary
Published 08/26/2021; Updated 09/12/2021

Here is a fun historical ride report of one of the most epic rides I have taken the club on.  I am still undecided if I will do it this year (please comment below if interested!).  While we have your mind on Greylock, the TT is indeed happening this year, September 11.  We’d love to see you participate- race it, volunteer, or both.  Head over to the Greylock Hillclimb TT page for more details.

Ride Report


Post by Tim_Cary »

We had Zinj, two Jonathan’s, Sam, Joe, Clayton, Mike, Todd & myself at the start. Perfect day for this ride- clear and cool temps all day (50-70 F).A rather rapid pace for a ride this long to start with…. rolling out of town through Conway and Shelburne Falls into Cherlemont at our first water stop. I had nearly 18 MPH at that point! Joe, Clayton & Todd headed home at that point, as the rest of us continued on up through Zoar- one of my favorite areas that goes between the railbed and the Deerfield River. And of course, the Whitcomb climb. I love Rte 2 up through Florida, but it was time to visit Whitcomb again. I burnt most of my matches there- awesome climb that I am sure had everyone swearing at me. Mike told us not to wait, as he was going back home after that via Rte 2, so after regrouping the remaining 5 of of us, we made our way down the Mohawk Trail the other way though the fun switchbacks into N. Adams. Then up Greylock we went. I heavily conserved and pretty much crawled up Greylock. But it was a beautiful clear day. We did not stay too long, and had a fun descent back down the north side, where Jonathan had a flat- lucky it was not on the descent. We rolled into our second refreshment stop to get more salt and sugar in us (at a fancy Cumberland Farms where “Walking on Sunshine”was playing and got stuck in our heads, perhaps appropriate!) before climbing back up to 116, where Jonathan had his second flat. At first it was nice to rest, but I wonder if the resting hurts more. Long slog up 116 through Cheshire and Savoy, and guess what- at the top, flat #3 for Jonathan! What a bad tire day. We could not find what kept causing it, but boy, glad I had two tubes! Then onward through Plainfield Center (second to last climb of the day!), and a nice descent to the shortcut over to Rte 9- Cummington Rd where wait for it…. Jonathan had is 4th flat! About this time, for some reason, I started getting more energy, and instead of being so far back, ZInj and I were wheel and wheel on several townlines and on the last climb into Goshen. Last stop in Goshen for final refreshments, and the fun descent down Rte 9 to Northampton- with Zinj doing a fair amount of work again on the flats. Got back in Northampton at 4:45- about 30 minutes earlier than last year. Great day, great guys to ride with.

This is what it looked like atop Greylock:


But before we got there, this is a cool snap from the hairpin descending into N. Adams:

Proof we made it:

The ride back is always painful as well, but pretty easy on the eyes: Image

Finally- we had some fun during all those flat tire times:


I had my Garmin VIRB camera along with me as well, and took selected scenes along the way. Some highlights are:

Climbing Whitcomb:
Descending the hairpin to N. Adams:
Descending Greylock:
Homeward bound in Chesire/Savoy:

Full video (58:10):

I’m still recovering from an epic day, but always look forward to this ride every year. We got back to Northampton at 4:45 this year- about 30 minutes earlier than last year. Fun day. Great company.