Best Crosscountry Skiing in Massachusetts

Trying to find the best crosscountry skiing 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

Connecticut, Windham County

03 :50 hrs
8.4 mi
58.043884 ft
Easy

George Washington Management Area offers around 4000 acres of beautiful wilderness. This skiing adventure loops through the heart of the park and features the forest of the area, Wilbur Pond, wildlife and an unnamed small pond. Wildlife that may be seen include cottontail rabbits, snowshoe hare, grey squirrel, white-tailed deer, fox, raccoon, muskrat, grouse, wild turkey, ring-necked pheasant, woodcock and waterfowl. Be apprised that dogs must be kept on a leash while on the trail.

2

Connecticut, Fairfield County

02 :56 hrs
5.2 mi
166.23541 ft
Moderate

The Zoar Trail, running through the Lower Paugussett State Forest, is blue-blazed, runs along the shores of Lake Zoar, through heavily wooded, rolling terrain. Some of the features of the ski include Prydden Falls, Lake Zoar (good ice fishing), great forest views and wildlife. The forest is full of maple, hemlock, beech and birch trees. Be apprised that dogs must be kept on a leash and that during hunting season you will need to wear bright colors.

3

Massachusetts, Monterey

03 :53 hrs
8.6 mi
73.72443 ft
Expert

This is a very popular place for snow sports and there are designated trails for different activity types so please stay on cross-country ski trails. Part of this trail is shared with snowmobile and snowshoe activities so please respect other trail users. This trail begins at Benedict Pond following a cross-country only trail and you will reach a lookout point with gorgeous snow-covered views. As you continue you will ski around the shoulder of Beartown Mountain and return on Benedict Pond Road, a multiuse trail. There are a couple steep sections and tight corners but the trails are wide.

4

Massachusetts, Great Barrington

04 :27 hrs
9.7 mi
115.828094 ft
Moderate

This is a popular place for snow activities and this is a multiuse trail so be aware of other trail users. You will begin at Benedict Pond and follow a lookout trail which offers gorgeous views and continue onto Benedict Pond Road. You will meet up with Mount Wilcox Road, reaching the summit of Mount Wilcox, before your long downhill return. There are several river crossings and some sharp corners but the trails are wide and easy to follow.

5

Massachusetts, Goshen

02 :05 hrs
1.8 mi
61.251892 ft
Easy

Located in D.A.R. State Forest, this trail follows Moore Hill Road from the parking area near Highland Lakes to Twinning Brook Pond. The trail has gorgeous scenery along the way and you will reach the top of a hill which has a fire tower and displays sweeping views over the valley and Mount Holyoke Range. There are several trails surrounding Twinning Brook Pond which allow you to explore the area before your return.

6

Connecticut, Fairfield County

02 :26 hrs
4.6 mi
85.466736 ft
Moderate

The Upper Paugussett State Forest Ski runs through a heavily forested area that offers a beautiful skiing opportunity. There are several different tree species here including hemlock, maple, birch, beech and oak. The trail follows bluffs along the shores of Shepaug River and Lake Lillinonah. There is some Indian lore that surrounds this area, a story that involves an Indian chief's daughter and her European lover that were both swept away in the river's rapids. Be apprised that dogs must be kept on a leash while hiking in this park.

7

Connecticut, Windham County

03 :50 hrs
8.4 mi
58.043884 ft
Easy

George Washington Management Area offers around 4000 acres of beautiful wilderness. This skiing adventure loops through the heart of the park and features the forest of the area, Wilbur Pond, wildlife and an unnamed small pond. Wildlife that may be seen include cottontail rabbits, snowshoe hare, grey squirrel, white-tailed deer, fox, raccoon, muskrat, grouse, wild turkey, ring-necked pheasant, woodcock and waterfowl. Be apprised that dogs must be kept on a leash while on the trail.

8

Massachusetts, Windsor

02 :16 hrs
4.7 mi
90.47772 ft
Hard

Notchview Reservation features more than 3,000-acres of rolling terrain that is most popular for its winter sports, especially cross-country skiing. This trail combines sections of both groomed and ungroomed trails, creating a wide loop throughout the reservation and a comprehensive tour of what the reservation has to offer. This trail reaches the top of a hill where there are great views of the surrounding rolling hills. The trails in Notchview Reservation are created especially for skiers but snowshoeing is popular as well to the side of the skiing trails.

9

Connecticut, Litchfield County

03 :06 hrs
2 mi
77.26691 ft
Hard

This cross country skiing adventure is located just west of the Barkhamstead Reservoir, and utilizes the tunxis trail running through a beautiful forest area offering a quiet, scenic ski. Some of the features of this trail include Kettle Brook, forest views and the Indian Caves. The forest is full of a variety of trees including red oak, maple, hemlock, tulip tree and ash. Be apprised that dogs must be kept on a leash while on the trail.

10

Connecticut, Litchfield County

04 :27 hrs
7.2 mi
204.0983 ft
Expert

The 2,300 acre piece of land that constitutes Macedonia Brook State Park came from the White Memorial Foundation in 1918. The park offers interesting ridge-line tours, peaceful forest, a gurgling Macedonia Brook and great views; this ski has all of these things. Another feature of this ski is Hilltop Pond, a descent place to fish for any interested. Be apprised that dogs must be kept on a leash while on the trail and there is a parking fee.

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