Best Hiking in Massachusetts

Trying to find the best hiking in Massachusetts? Bivy has great hiking, biking, paddling, climbing, skiing, riding and more, with hand-curated trail maps, as well as detailed driving directions.

1

Massachusetts, Great Barrington

02 :30 hrs
6.3 mi
193.83307 ft
Hard

This trial will take you all the way around Monument Mountain and to its high peak, called Squaw Peak. As you hike around the mountain you will walk along a narrow hiking path through the deep, quiet woodlands, past beautiful flowers and a waterfall. At Squaw Peak there is a large, free-standing pillar of stone called Devil’s Pulpit and there are amazing lookout points over rocky cliffs. The views from Squaw Peak include the Housatonic River Valley, The Berkshires, the Taconic Mountains, and the Catskill Mountains.

2

Massachusetts, Worcester County

01 :05 hrs
2.9 mi
9.104996 ft
Easy

Nice walk around the pond. Be aware the Blue Trail just ends. But if you follow the railroad tracks to the left, then Freedom Street to the Hopedale Pond Dam, then Hopedale Street, you'll get back to the start.

3

Massachusetts, Williamstown

01 :11 hrs
3.1 mi
92.845795 ft
Moderate

This trail is in the northwestern corner of Massachusetts in the Taconic Mountain Range. You will begin your hike at the Buxton Garden and hike up into the thick hardwood forest. As you climb you will notice spots on the trail where you can look back for a view over Williamstown. You will hike down along the Birch Brook for a bit before climbing up to a ridge. The trail will then follow the ridge all the way back down to your car. This forest is filled with an array of wildlife, watch for signs of these on your hike.

4

Massachusetts, Essex County

00 :51 hrs
2.2 mi
21.745916 ft
Easy

Start your walk in downtown Marblehead and end up at Fort Sewall. Look out over Picturesque Marblehead Harbor.

5

Massachusetts, Berkshire County

00 :52 hrs
2.1 mi
90.469025 ft
Moderate

Kennedy Park in the Berkshires. Wide paths and helpful signs along the way.

6

Massachusetts, New Ashford

03 :41 hrs
3.3 mi
336.42255 ft
Hard

This hike follows the Appalachian Trail and is well-marked and easy to follow. You will tour through a variety of woodlands, grassy meadows, and past pretty streams as you climb Saddle Ball Mountain and follow the ridge up to Mt. Greylock. The majority of this hike is on the mountain ridge allowing for many lookouts, both near and far, along the path. You will first hike through Jones Nose which is a large meadow with a great view and a variety of wildflowers. The end of the trail is at the summit of Mt. Greylock, the highest peak in Massachusetts, where you will find historic monuments and views of the Taconic Mountain range, Hopper Valley, and the cities below.

7

Massachusetts, Hampshire County

02 :54 hrs
6.2 mi
192.54889 ft
Hard

Very hilly

8

Massachusetts, Hampshire County

02 :16 hrs
4.8 mi
213.07938 ft
Hard

Beautiful views of the Pioneer Valley. It can be strenuous at times but is fairly easy. It combines the orange trail and the white trail.

9

Massachusetts, Essex County

00 :34 hrs
1.7 mi
6 ft
Easy

Nice walk along the Spring Pond in Peabody, MA.

10

Massachusetts, North Adams

02 :33 hrs
5.8 mi
345.51617 ft
Hard

The majority of this trail is at a high point, as it follows the ridge, providing great views for the duration of most of the hike. Mt. Greylock’s peak is the highest point in Massachusetts and the views are phenomenal. Following the Old Summit Road on the way back down provides a change in scenery and brings you near the Money Brook Falls which can be easily accessed via Hopper Trail.

See more adventures..

Explore complete list