Introducing: The Berkshire Triple Crown

When life gives you mountains, invent your own little Giro d’Italia.


I came up with the idea in June, on my first post-surgery climb of my old mistress, Mt. Greylock. Massachusetts is my favorite state, and my home, and for the most part, cycling is thriving. Boston’s hubway and cycling infrastructure set a standard for the northeast, cycling clubs are sprouting like wildflowers, and the Pan-Mass Challenge continues to be a national event, with riders coming from the opposite coast just to participate.

Still, the humble Berkshires remain an undiscovered cycling paradise. Some major events exist, like the Josh Billings Runaground Triathlon or the Northampton Cycling Club’s Greylock Time Trial. In my neck of the woods, North Adams, a tiny glimmer of arts and culture in an otherwise mountainous and rural corner of the state, cycling is a rare bird.

So, I invented a race. Come, cyclists, ride with me!

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The route’s objective is to tackle three of the toughest climbs in the state. First, Route 116 into Savoy supplies some extremely steep, winding roads in the pastoral Savoy/Plainfield/Cheshire region of Western Massachusetts. Second, the Whitcomb Summit gives you an unrelenting crawl out of North Adams that peaks at the incredible 60-mile vista near the Elk Monument. Finally, the highest peak in Massachusetts, Mt. Greylock, puts an epic stamp on a ride that takes you to every single one of my favorite places in the Berkshire hills.

Part tourist escape, part masochistic ritual!

Stage I: Rt. 116 to Plainfield Pond

The first hill, Henry Wood Road.

Start in North Adams, and head south on Church Street until you see McCann Technical School, and hang that left onto East Road for several miles of rolling warm-up.

Mt. Savoy is a wide, formidable mountain spanning several towns, and is the furthest destination in the Berkshire Triple Crown. Plainfield Pond isn’t quite the summit, since the actual highest point is between someone’s farm and the woods. It doesn’t boast the panoramic views of Greylock or Florida, but the climb will leave you gasping and the incredibly beautiful beaches at this glacial pool will keep your breath caught in your throat.


Nestled in coniferous forest, the pond is a gem that isn’t flooded in tourist traps and scenic view towers. Dip your feet in and relax before heading back down the mountain along 116. Don’t worry- we’re taking a detour before Adams.

When you see red, take a right.

There’s a dirt road off to the north from 116 called Burlingame Hill, which takes you down to the epic view your legs will be craving after the pasture Savoy calls a summit. Here’s a taste:



Next stop, breakfast. Head back down Burlingame Hill to the bottom, but use caution; the grade can hit 15% or more. Once you reconnect to East Rd, take a right on Upper East Hoosac Street to the best breakfast joint in Adams, The Daily Grind.


The Grind is a staple of any good Berkshire recreationist’s diet. With an expansive menu that waxes and wanes between the traditional and the absurd, there’s something for everyone.


I fuel up with some classic toast and eggs and head back up to East Road for the next summit, Mt. Florida.

Stage II: The Mohawk Trail to the Whitcomb Summit


Coming down Church Street, you can swing left towards the Massachusetts College of Liberal Arts’ athletic complex, a nice vertical sprint before… well, more climbing. Route 2, also called the Mohawk Trail, is the most iconic entry into this part of the Berkshires. Often referred to simply as the Hairpin Turn, this climb swings around at the Golden Eagle Restaurant for the view above, but it’s a teaser. We’re going to the opposite side of the summit.

Climb… Climb… Climb…. Tired yet?


Two down, one to go. Don’t head back down to North Adams until after you’ve had your picture taken with the Elk Monument. I’ll have to let my bike stand in.


Before tackling Greylock, you’ll need to replenish some lost nutrients. That’s why God invented the superfood, the only sports fuel I’ll ever fully endorse: Jack’s Hot Dogs.


Fit for a king, fit for a cyclist. Three or four of these babies will be all the extra weight you need to get that serious calf burn you can’t find on the East coast.

Stage III: Mount Greylock

Head west along Route 2 past Mass MoCa, and hang a left at Notch Road. You can’t miss it; there’s a big sign for the Mt. Greylock State Reservation. This is what locals refer to as the “Steep Side” and cyclists refer to as “Career Suicide.”


Once you’re at the base of the mountain, you’ll want to pull a few yoga poses. Stay limber! There’s no turning back now! The Mt. Williams Reservoir will help keep your spirits up before you face the winding climbs on Mt. Greylock.


Notch Road runs all the way to the summit along a pretty steep path. After the first four hairpins, the grade does let up until the summit. You’ll even peek the Veteran’s War Memorial Tower, affectionately known as the Beacon, somewhere along the ridges of Greylock’s lesser slopes.

See it?

When you feel like you’re about to break, when you sit back and stagger at the sheer veracity of the climb, it’s over. And just like that, a race is born.



So, how did we do?

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Almost 7,000 feet of vertical climbing and 60 miles of pedaling, with a final elevation of 3, 491 feet. I met my dad at the top, who swapped a wreath and two trophy girls for a big glass of water and an ice cold beer. It couldn’t have been a more perfect day to ride, and it encapsulates everything I love about the Berkshires. From the home-cooked restaurants that locals uses as a second kitchen, to the epic views that put our town permanently on the map as a vacation destination, the Berkshires fully represents the wild, untamed green mountains that define the Northeast.

So, next time you’re considering a cycling mecca, save a buck on that ticket to Italy and see what’s hiding in your own backyard. There’s likely a triple crown right out your front door.

Keep Riding!








5 thoughts on “Introducing: The Berkshire Triple Crown

  1. Pingback: Lenore Koch
  2. Pingback: Daryl Bujak

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