By Tim Cary
Published 09/03/2023; Updated 09/03/2023

Why super?  Well, today’s ride goes way above and beyond any sort of standard Saturday Morning Ride length and elevation.  We used to do these type of rides once a month for the season, and they were pretty popular.  So, today we rode to, and up Mt. Greylock- the highest peak in Massachusetts.

Today’s ride came about for two reasons. One was my personal craving to ride to Greylock- as my last ride to there was 2016. But, amazingly the second reason was that I had more than several club members ask me if I would organize this ride.

Before I get into the ride report, please join me in congratulating Elissa and Eddie on their first Greylock ascent.  The other five of us had climbed it several times before today and knew what we were in for.  It is a huge accomplishment not only pedaling up the highest peak in Massachusetts, but- pedaling TO it, and back home as well!

After a few days of discussing the route plan with our “King” of alternative routing, I decided on a remote start from Shelburne Falls, as a majority of those whom asked me to do the ride reside closer to there, and makes the ride to Greylock more manageable (though, less epic from Northampton!). The route kept us off the major roads, and also had us descend Greylock on the south side.

Seven riders rolled out around 7 AM under slightly foggy skies and with temperatures around 50 F.  A bit of fall in the air, and one of those rides where you have to decide to keep the warmers and vests on, or tough it out as you warm up.  Speaking of warming up, it was not long until we felt like we were climbing Greylock, as out of Buckland, climbing up Charlemont Rd with a 15%-er in there. At least it was not a very long climb.

After a chilling descent into Charlemont along the Deerfield river, we crossed Rte 2 over into Zoar.  If you know the area, you know what that means when heading to Greylock.  Yes, I (we??) opted to take Whitcomb Hill Rd.  It hurts and never seems to end, but it is also very scenic and quiet.  At least I vetoed the Kingsley route 🙂  Before the climbing began, Eddie had a mechanical, which was quickly resolved by our resident King of routes.  At Whitcomb summit, we took a pause to enjoy the view and let the bikes cool down.


The descent down into North Adams is always very beautiful and fun.  Rte 2 has been freshly paved with a clean shoulder, so that helped too. I love the sharp switchback with the restaurant on the corner, while taking in the views.  The breeze was picking up at this point, and it was a cross-wind, so I had to take it easy this time, as my deeper wheels tend to cause a little shaking.

Once we got into the center of North Adams, we noticed Benny was nowhere to be found.  We stopped for a quick break while I dialed up Benny- where are you? “I am climbing Mt Greylock”.  OK then!

Ten minutes later, the rest of us began the ascent up the north side of Greylock.  We were all spaced out and climbed at our own pace.  It was nice to not chase anyone or look for a PR, and enjoy it.  It was also nice that most of the climb was in the shade, and the temperature was prefect.  I had not been up Greylock since 2018 (when I did the club race) .  Not much has changed.  All the switchbacks and steep bumps were still there. I was just a lot slower this time.

At the summit, it was just about as perfect as you can get this time of year.  Not even cold, but not hot.  Clear views for miles.  We took time to hydrate, put in some calories, and take in the views and what we had just all accomplished.


But, even though it seems all downhill from here, the ride was only half over, which meant more climbs!  It was a fun descent down the south side of Greylock- one that I have only done a few times.  Much less “steepness”, less curves, and as a result, more pleasure.

At the bottom, our route took us onto the Ashuwillticook Rail Trail.  I have only visited this trail once, way back in 2012- and only a small portion.  I had no idea how long and beautiful it was.  It is well maintained, and runs along the scenic Chesire Reservoir.  We were disappointed when we had to turn off of it to head up into Savoy.


So the thing about this route, and type of ride….. at this point, everyone just wants to get home.  And, with the lack of places to stop and refuel, supplies were getting low.  When we got to the center of Savoy, options were discussed- one being, climbing into Windsor for the store. But, we decided to press on.

Climb, climb, climb into the center of Plainfield.  I remembered from Don Frank, that the Plainfield town office had a water spout.  So, I pulled over to check.  Indeed, cold, fresh water was had by all.  As a bonus, there were apple trees there- that hit the spot!

The descent into Ashfield was welcome.  We headed over to the Bear Swamp area… one of my top five places to ride all times of the year.  So beautiful and peaceful.  Once we got to Rte 112, a quick vote was taken to simply head downhill back to Shelburne Falls, rather than stick to the more scenic route over Baptist Corner.  On the descent I encountered the same crosswind issue I mentioned earlier- and as such, the ride leader got dropped and rode solo back to Shelburne Falls.

When I got back to my car in Shelburne Falls around 3:30PM, I had 91 miles, and 8885′ of climbing.  Couldn’t asked for a better day or weather for this ride, and I am so grateful for the group of riders that join me on these crazy adventures!

Do you want to bike up Greylock?  Consider signing up for the Greylock Hillclimb Time Trial, which is happening next weekend.  It is a fun, low-key event. Ride it to support NCC!