Top 5 Road-bike Rides in the Berkshires

Mt. Greylock (51 km)

Mount Greylock is the one of the best cycling destinations in the whole state of Massachusetts. At 3,491ft., it is the highest point in the state making the ascent challenging or extra challenging depending on which route you choose.

Notch Road from North Adams is the more challenging of the two roads to the summit, with hairpin turns and some very steep sections in the first half of the climb. For a more moderate, but still challenging route, it is recommended to bike to Lanesborough, then taking the 10 mile ascent on Rockwell Road where there are several scenic vistas on your ascent, and a thrilling coasting descent back to North Adams or Williamstown on the north side.

  • Keep in mind when preparing for your trip that it is often significantly cooler on the summit than at the base of the mountain and to pack a windbreaker for the descent. It is also recommended to check your brakes and avoid the heavily trafficked times of year such as fall weekends.

Great Barrington to Umpachenee Falls (49 km)

This route takes you through some of the most pristine sections of the Berkshires, ending in the small town of Mill River, Massachusetts where there is a rolling waterfall that descends over rock ledges. The trip takes about a half of a day and begins from Great Barrington.

First you travel through Sheffield, near the oldest covered bridge in Massachusetts, turning left onto County Road toward the center of town. From here there are some wonderful views of the Housatonic River which you cross and ride through some agricultural lands, soon crossing over into Connecticut.

Make your way to the Clayton-Mill River Road, and when you see a bridge, you’ll turn right on a gravel road over the river you’ve been following. Just after this wooden bridge, turn right into the park. Before heading back, you can buy drinks and goods from the Mill River General Store. To return, take Rt. 183 back toward Great Barrington.

Great Barrington to Philmont, NY (79 km)

This trip will offer some of the most dramatic changes in landscape of any ride in the Berkshires with such a short distance. Take Rt. 23 past corn fields onto Rt. 71 by the rural airport into the quaint town of North Egremont and into Alford.

Take a left onto Rt. 22 for an ascent over the last of the Berkshires for a descent into the remarkably different view of the Hudson Valley and the Catskills in the distance. Passing this beautiful farmland, take a right onto Rt. 21 which you take along a stream, past a number of rural farms until you reach Harlemville where you can rest and refill your rations at the Hawthorne Valley Farm Store, a pace which sounds and feels much like a town in rural Germany, much attributed to this Rudolph Steiner-inspired community.

Follow this road into Philmont where you can get off your bike at the High Falls Conservation Area to check out these massive water falls before returning via Rt. 23 through Craryville and Hillsdale.

Great Barrington to Tyringham (52 km)

This is a varied ride beginning with the ascent by Ski Butternut circling around Lake Bue, passing the Berkshire Fish Hatchery in Hartsville. Continue on to Monterey, MA, where there is a great stop potential at the Monterey General Store. You then can stop for a swim at Lake Garfield before a dramatic descent into the Tyringham Valley.

Riding though South Lee, and onto Rt. 102 you will end up in Norman Rockwell’s favorite town to depict of Stockbridge which features many attractions including the Norman Rockwell Museum and Chesterwood.

Then bike along one of the most scenic stretches in the southern Berkshires along the Housatonic River into the hamlet of Housatonic with its old mill buildings and stop at the Berkshire Mountain Bakery for a fresh pastry before your return into Great Barrington.

An alternative route is to head into Lenox after Tyringham and ride past Tanglewood on Hawthorne Rd., Lake Mahkeenac and historic mansions above downtown Stockbridge such as Naumkeag before joining the other route along the Housatonic.

Mohawk Trail: Williamstown to Deerfield River Ride (96.5 km)

This is no easy ride, but it is one of the most spectacular rural rides in Southern New England. After a steady ascent along Rt. 2 from North Adams to the Western Summit where you can see breathtaking views of the mountains and valley below.

After a 30-40 mph descent, find your way to River Road where you will bike along the wild Deerfield River, often run by white-water enthusiasts from all over the New England region. Pass the Hoosac Tunnel and take Rt. 100  to Rt. 8 south-bound until you find yourself back in North Adams where you can enjoy world-class museums such as Mass MoCA.

Some of these routes were selected from Bike New England’s blog at: https://bikenewengland.com/bicycle-rides-in-the-berkshires/