Massachusetts - Top Bike Climbs

#1
Mt. Greylock North
USA, MA
#2
Whitcomb Hill Rd
USA, MA
#3
Kingsley Hill Rd
USA, MA
#4
Mt. Greylock South
USA, MA
#5
Monroe Hill
USA, MA
#6
Mohawk Trail West
USA, MA
#7
Petersburg Pass East
USA, MA
#8
East Hawley Road
USA, MA
#9
Wachusett Mountain North
USA, MA
#10
Mount Holyoke
USA, MA

Climb List: Massachusetts
(sort by distance, difficulty, elevation and more)

Cycling Massachusetts

Mt. Greylock, as seen from North Adams, aerial view

Mt. Greylock, Massachusetts’ #1 Bike Climb

as seen from North Adams.

There are some extremely difficult bike climbs in Massachusetts.  The toughest ones get that designation because of their extreme grades, not because of length or altitude.  While Mt. Greylock is ranked #1 in Massachusetts, there are a couple climbs that are short but so steep they are almost impossible to climb.

All Top 10 Massachusetts bike climbs, other than Wachusetts Mountain and Mount Holyoke, are clustered in the northeastern corner of the state near its border with New York.

Map of Top Bike Climbs in Massachusetts

Williamstown, Massachusetts

Williamstown is the hub of top Massachusetts bike climbs.

Aerial view of town of Williamstown during fall

We love Williamstown -- it has a lot to do in addition to cycling.

The following are Massachusetts’ Top 5 Bike Climbs:

TOP BIKE CLIMB IN MASSACHUSETTS

MOUNT GREYLOCK NORTH

Cycling Mt. Greylock, Massachusetts  - photo collage, PJAMM Cycling logo in corner, Mt. Greylock Veterans Memorial tower, road sign reading "Welcome to Massachusetts", and bike parked against sign saying "Welcome! Mt. Greylock Summit Elevation: 3,491'"

Highest point in all of Massachusetts.

 Cycling Mt. Greylock, Massachusetts  - PJAMM Cyclists stand with bikes in front of the Veteran's Memorial Tower

Ride nine miles gaining 2,772’’ at 5.7% average grade.

Cycling Mt. Greylock, Massachusetts  - bike parked in foliage on roadside next to sign for Mt. Greylock, Scenic Byways; PJAMM Cycling logo in corner

Mt. Greylock is a fun, scenic, and fairly challenging bike climb in the Mount Greylock State Reservation, Massachusetts.  The climb has some sections that hit 15%, the steepest quarter mile is 12.2%, and one mile averages 10.2%  The climb is through Mount Greylock State Reservation, and we finish at the spectacular Mount Greylock Veterans War Memorial Tower.

Cycling Mt. Greylock, Massachusetts  - photo collage, route map and gradient, fall foliage lining roadways, PJAMM Cycling logo in corner

Cycling Mt. Greylock South, Massachusetts - aerial drone views of Veterans Memorial Tower atop climb's summit, fall foliage

#2 BIKE CLIMB IN MASSACHUSETTS

WHITCOMB HILL ROAD

Bike parked in center of field surrounded by fall foliage and bright blue sky

Cycling Whitcomb Hill Road

Ride three miles gaining 1,441’ at 9.1% average grade.

views along the Whitcomb Hill Road, Massachusetts, bike climb

No distant views, but a fantastic ride, particularly during fall colors.

#3 BIKE CLIMB IN MASSACHUSETTS

KINGSLEY HILL ROAD

Bike parked against guardrail on very steep segment of roadway

Enough said -- that’ll get you #3 for just a 1.5 mile climb.

#4 BIKE CLIMB IN MASSACHUSETTS

MOUNT GREYLOCK SOUTH

Cycling Mt. Greylock South, Massachusetts  - aerial drone view of Mt. Greylock during fall, bright New England Fall Foliage, Appalachian Trail in middle and Rockwell Road on right

Memorial Tower center top, Appalachian Trail middle, Rockwell Road right.

Cycling Mt. Greylock South, Massachusetts - photo collage, blue skies, bright green fields, and fall foliage on the first third of the Mt. Greylock South climb, PJAMM Cycling logo in corner

Cycling Mt. Greylock South (Lanesborough)

Ride 8.9 miles gaining 2,279’ at 4.5% average grade.

Cycling Mt. Greylock South, Massachusetts  - photo collage, bikes leaning against railing overlooking views from summit, bikes in front of Veterans Memorial Tower, and plaque at top of climb, PJAMM Cycling logo in corner

#5 BIKE CLIMB IN MASSACHUSETTS

MONROE HILL

bike parked against power line next to two-lane roadway surrounded by dense foliage

Cycling Monroe Hill

Ride 1.3 miles gaining 737’ at 10.7% average grade.

Not as steep as its neighbor Kingsley Hill Road, this one will still challenge you, particularly in the middle section with a 13.5% quarter-mile average grade.

views along the Monroe Hill, Massachusetts bike climb

Monroe Hill is a peaceful climb along a lightly used road surrounded by forest.