Mount Wachusett - Cycling

Made possible by




A fun ride through inland Massachusetts ascending a 2000ft mountain with views of the Boston skyline.

Written by

Eric Gilbertson


60.0 miles

The three distance options are 26 miles, 60 miles, or 100 miles.

Destination Distance From Downtown

43.3 miles


4 of 5 diamonds

The full 100-mile ride is difficult but shorter options of 60 miles or 26 miles make it easier.

Time To Complete

1 days


Spring, Summer, and Fall

Dog Friendly


Fees Permits




This is a great ride for experienced cyclists, bringing you through small towns, rolling hills and forests on the outskirts of Boston. A grueling climb up the 2000 ft tall Mt. Wachusett at the very end rewards you with panoramic views of the Berkshire Mountains to the west, Mt. Monadnock to the North, and the Boston skyline to the east. Return to Boston for a full-day century ride (100 miles), or take the commuter rail back for a 60-mile ride. The ride mostly follows quiet back roads, with an option of including the Minuteman bike trail.

What Makes It Great

This ride is a great opportunity for cyclists to put on some miles and get in lots of climbing in a scenic location. While most of the route from Boston to near Westminster passes over gently rolling hills, the last five miles are packed with over 1300 ft of ascent! That will really get your quads burning.

Start your ride by following the Minuteman rail trail from Boston to Concord. No cars here to deal with – just other cyclists and joggers. After Concord follow 2A or nearby backroads to the town of Westminster. You’ll know the climbing is about to start when you see the wooded hill in the distance with ski runs crisscrossing down. That’s Mt Wachusett, which is a popular skiing destination in the winter.

Don’t be too intimidated - there’s a road switchbacking up to the summit. Start up the road from the east side of the mountain, and a few miles later you’ll be at the top! The views there are amazing. Because Mt. Wachusett is the biggest hill around, you can see almost your entire bike route back to Boston in the distance. Mt. Monadnock looms up to the North in New Hampshire, and the Berkshire mountains dot the western horizon. Autumn time is especially beautiful there with colorful leaves all around.

When you’re done with the view, you can either retrace your route back to Boston on bike, or make a loop by taking different backroads like 117. If you’re tired out and just want a relaxing return journey, no problem! There’s a commuter rail stop just 13 miles away in Leominster. Hop on with your bike and enjoy the ride back to Boston.

Who is Going to Love It

Experienced cyclists will love the scenic miles and steep hill climb to the summit. It’s hard to find a bigger climb this close to Boston, and it makes a great lunch stop in the middle of a century ride.

But you don’t need to be an experienced cyclist to enjoy Mt. Wachusett. There are plenty of hiking trails winding up the mountain if you’d rather park your bike at the base and walk up for the great view. And if 60 miles is more your cup of tea, just use the convenient commuter rail at Leominster for the return journey. You can even start and end your journey at Leominster for a 26 mile round trip ride. There are options for everyone!

Directions, Parking, & Regulations

You can start this ride from anywhere in Boston for the 100-mile and 60-mile options, following the Minuteman trail and either 2A, 117, or nearby backroads to Mt. Wachusett. The nearest commuter rail stops to Mt. Wachusett are in Leominster and Fitchburg, both about 13 miles away by bike. If planning to take you bike on the Commuter Rail on a weekday, ensure that you avoid peak hours when bikes are prohibited. (Generally 5-9 am inbound, 4-7p  m outbound, but check for more details).

Similar Local Cycling Spots

See all

More Boston Activities

View Boston

More Mount Wachusett - Cycling Activities

Boston Recommendations

Local Boston Stories


Mount Wachusett - Cycling

42.489506, -71.886979

Get Directions