The hardest cycling climbs in Massachusetts. From this page you may navigate to the top 10 most difficult bicycling climbs in MA.
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.
Williamstown is the hub of top Massachusetts bike climbs.
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
Highest point in all of Massachusetts.
Ride nine miles gaining 2,772’’ at 5.7% average grade.
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.
#2 BIKE CLIMB IN MASSACHUSETTS
Cycling Whitcomb Hill Road
Ride three miles gaining 1,441’ at 9.1% average grade.
No distant views, but a fantastic ride, particularly during fall colors.
#3 BIKE CLIMB IN MASSACHUSETTS
Enough said -- that’ll get you #3 for just a 1.5 mile climb.
#4 BIKE CLIMB IN MASSACHUSETTS
Memorial Tower center top, Appalachian Trail middle, Rockwell Road right.
Cycling Mt. Greylock South (Lanesborough)
Ride 8.9 miles gaining 2,279’ at 4.5% average grade.
#5 BIKE CLIMB IN MASSACHUSETTS
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.
Monroe Hill is a peaceful climb along a lightly used road surrounded by forest.