Western Massachusetts Berkshire Backroad Gravel Grinder (AKA: B2G2)

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West Stockbridge, MA
Date Published:
May 21, 2022
Gravel Ratio:
60% G / 40% P
Difficulty Rating:
Enjoyability Rating:
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This route is brought to you by Sarah Hills, one of our 2022 Route Ambassadors (and hill loving 😉) gravel enthusiast from Conway, Massachusetts.
Photo Credits: Sarah Hills


One of my favorite early spring gravel rides is this B2G2 route supported by Berkshire Velo. The route is also paticularly stunning in Autumn when the leaves turn.

The route crosses back and forth over two sets of Berkshire “hills”, a rural region dotted with villages and small towns. A popular vacation destination, the Berkshires are known for a thriving arts scene, fall foliage, farm-to-table food, and numerous outdoors activities year round. The ride takes you through many small towns on a back door tour of TurnPark Art Space, Tanglewood (Boston Symphony Orchestra), Chesterwood Museum, Norman Rockwell Museum, Wheatleigh, Kripalu Yoga Center, and Berkshire Botanical Garden.

The sights are outstanding all along this route. There are summit overlooks as well as numerous lake, pond, and reservoir views. You also pedal past historic estates, gardens, sculptures, and the Stockbridge Bowl/Lake Mahkeenac.

The view over Gould Meadows is stunning. The arduous climb up Reservoir Road is a grinding 12% but the descent through the woods down the other side makes it well worth it.


The sharp right hand turn off of Great Barrington Road (Rt. 41) onto the Housatonic Rail Trail is easy to miss. Be sure that you are doubling back by the River.

Do this ride if you value cultural landscapes, historic properties, and the arts. It is best if you also enjoy climbing hilly terrain as you cycle past these properties. The long views are the big payoff!

Other Notes:

You may park anywhere in “downtown” West Stockbridge, but there is ample parking near the town water department on Moscow Road.

Any tire 32 or up are fine for this ride; however, the woods sections are definitely more enjoyable on a wider tire.

You could easily add a short spin through Stockbridge to see the famous Alice’s Restaurant, Naumkeag Public Garden, and Mission House.

Driving Directions

Route Contributor

2022 Ambassador: Sarah Hills

I’m Sarah, originally from “the bucolic part of New Jersey” where, when I wasn’t smashing tennis balls on the court, I was spending hours exploring bridal trails and hiking paths on a bike. Ultimately settling in western MA, I prefer to ride dirt roads, class 4/5 roads, and the single track of New England and Canada.

An inquisitive person by nature with a belief that routine is the enemy, I live for getting out into uncharted territory where I thrive climbing hills, hopping over rocks, and traversing gnarly terrain, whether it be farmland or the backwoods. I tease that if my surname wasn’t Hills, it would, undoubtedly, be Woods.

Cycling has helped me learn to be more self-sufficient and I have only needed a ride home once in 9 years of serious cycling. I have become unafraid of negotiating the male-dominated realm of the bike shop and I have learned to maintain my own bikes, the exception being…I don’t bleed brakes! A two-time stage 4 cancer survivor, I credit the bike with helping me rebuild my body while maintaining my sanity and teaching me an immense amount about myself, control, and limitations.

Though I’ve done some CX and MTB races, I am partial to riding any gravel anytime with my partner and cycling inspiration, retired Masters World and National Cyclocross champion Kathy Sarvary, as well as mountain biking with my son, Fisher. When I am not busy torturing my two Jack Russell Terriers, I spend time practicing my other passion for landscape, design, and building projects. Though, never straying too far from the bike or my fellow riders, I enjoy supporting local NEMBA and NCC chapter events, as well as volunteering for community projects such as Franklin Land Trust’s D2R2 annual fundraiser. I believe you are one ride away from a better mood!

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