Best Trails in Massachusetts

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


Massachusetts, Great Barrington

02 :30 hrs
6.3 mi
193.83307 ft

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.


Massachusetts, Worcester County

01 :05 hrs
2.9 mi
9.104996 ft

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.


Massachusetts, Williamstown

01 :11 hrs
3.1 mi
92.845795 ft

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.


Massachusetts, Essex County

00 :51 hrs
2.2 mi
21.745916 ft

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


Massachusetts, Berkshire County

00 :52 hrs
2.1 mi
90.469025 ft

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


Massachusetts, Ipswich

02 :02 hrs
20.4 mi
31.720919 ft

Ipswich is one of the most beautiful towns in the state of Massachusetts with expansive beaches, forests, farmland, country estates, and winding rivers as well as gorgeous architecture and history. The Ispwich River Ramble is an enjoyable flat route with a few short hills, one of which allows you to visit the Crane Estate on Castle Hill. One section on State Route 1A can be busy and congested but the rest of the route is on quieter country roads. On this ride you will visit Crane Beach, Castle Hill which features a grand estate and stunning views, ramble through vast salt marshes, tour open farmland, and border a section of the Ipswich River.


Massachusetts, Lanesborough

03 :28 hrs
35.6 mi
852.1644 ft

This is a strenuous ride that is steep uphill for over 7 miles as you conquer the state’s highest summit, Mount Greylock. This arduous climb is not without reward. The paved roads up to the summit offer beautiful scenery and many observation points along the way and the views from the summit are stunning, including panoramic views stretching 100 miles into six states. The descent is fast and the end of the ride is on gentle roads. These mountain roads can have lots of traffic, especially on holidays and weekends. This area is also very popular for hikers and there are numerous trails that begin on and cross these mountain roads. Caution is advised.


Massachusetts, Concord

10 :01 hrs
101.4 mi
548.1423 ft

This is an epic journey through central Massachusetts from historic Concord, to peaceful Princeton. At Princeton, you will climb Mount Wachusett. This is the biggest climb on the route and offers spectacular views from the top but the rest of the terrain is very hilly as well. The route is mostly low traffic roads or roads that offer wide shoulders with a few major roads crossing and short sections riding along busy roads with a narrow shoulder. As you ride the quiet, country roads you will also visit several quaint towns and view some beautiful ponds and reservoirs. This ride is based on a ride run annually by the Charles River Wheelmen, called Climb to the Clouds.


Massachusetts, New Ashford

03 :41 hrs
3.3 mi
336.42255 ft

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.


Massachusetts, Hampshire County

02 :54 hrs
6.2 mi
192.54889 ft

Very hilly

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