The Berkshire Mountains of Western Massachusetts offer some of New England’s most spectacular winter hiking opportunities. From the snow-covered summit of Mount Greylock to the peaceful trails of October Mountain State Forest, winter transforms the Berkshires into a pristine wilderness playground. However, successful winter hiking in this region requires thorough preparation and respect for the elements.
Prepare with Essential Winter Gear
Before hitting the Berkshire trails this winter, proper equipment is crucial for both safety and enjoyment. A well-prepared winter hiker should carry:
- Microspikes or Crampons: Essential for icy conditions, particularly on popular trails like those at Mount Greylock and Monument Mountain.
- Snowshoes: Necessary after significant snowfall, especially in areas like Pittsfield State Forest.
- Insulated, Waterproof Boots: The Berkshire winters are notorious for deep snow and cold temperatures.
- Layered Clothing: Start with moisture-wicking base layers, add insulating middle layers, and finish with a waterproof outer shell.
- Emergency Kit: Include a headlamp, first aid supplies, a fire starter, and an emergency shelter.
- Navigation Tools: Map, compass, and GPS device with extra batteries.
Food and Drinks: High-energy snacks and plenty of water in insulated containers.
Mount Greylock, Wiliamstown
At 3,491 feet, Mount Greylock is the highest point in Massachusetts! It offers views 60-90 miles in the distance of four states and five mountain ranges. There are several trails leading to the top of Mt. Greylock so choose a trail that is a good fit for you! (There is a road to the top as well Bascom Lodge with overnight accommodations and food options- open Memorial Day to Labor Day)
Ice Glen Trail, Stockbridge
Behind the quaint downtown of Stockbridge sits a stunning area to hike! The Ice Glen Trail’s unique path runs through a forest of pines and takes you through boulders, which is what makes this a moderate 1.4-mile out-and-back trail.
Olivia’s Overlook and the Charcoal Trail, Lenox
Olivia’s Overlook and The Charcoal Trail offer amazing views in the Berkshires located on Lenox Mountain Road. This popular overlook is connected to The Charcoal Trail, a 6-mile trail including a 2-mile loop. It’s located only minutes from downtown Lenox!
Bash Bish Falls, Egremont
Bash Bish Falls is the tallest waterfall in Massachusetts! It is at the southern tip of the Berkshires and has a drop of 80 feet into a plunge pool. Located in a peaceful forest setting, you’ll walk a mile up along Bash Bish Brook to get to the falls. This trail has a moderate rating and is about 2.1 miles round trip.
Project Snowshoe, Williamstown
Williamstown is a college town in the northern Berkshires. During the winter, The Clark Institute’s 140 acres are open for exploring by snowshoe, also known as Project Snowshoe. Complimentary snowshoes are offered if you don’t have any. Visit the museum, snowshoe around the property, and warm up in the cafe with a bowl of hot soup!
Hike to Laura’s Tower, Stockbridge
In the center of Stockbridge behind the quaint downtown of shops and restaurants Laura’s Tower is a beautiful area to hike in Sedgwick Reservation. The trail is 1.8 miles, round trip, up to Laura’s Tower where you see close to 360-degree views at the top! There is a steep set of steps with a railing for support.
Hiking Safety
Winter hiking in the Berkshires demands extra attention to safety. From being prepared for any weather conditions to knowing how to properly navigate various terrains, safety should always be a priority before heading out on a hike!
Weather Awareness Tips:
- Check multiple weather sources before departing
- Be prepared for rapid weather changes common to the Berkshire mountains
- Consider wind chill factors, which can be severe at higher elevations
- Start early to take advantage of limited winter daylight
Navigation Tips:
- Trails can become obscured by snow
- Carry both physical maps and GPS devices
- Know how to use a compass in case electronics fail
- Familiarize yourself with trail markers and blazes before they’re covered in snow
7 Best Practices for Winter Hiking
To ensure a safe and enjoyable experience:
- Never hike alone in winter conditions
- Start early to allow plenty of daylight for your return
- Sign trail registers when available
- Tell someone your planned route and expected return time
- Be prepared to turn back if conditions deteriorate
- Stay hydrated – winter dehydration is common but dangerous
- Monitor yourself and your companions for signs of hypothermia and frostbite
The Berkshires offer an unparalleled winter hiking experience that combines challenging terrain with spectacular natural beauty. From the historic paths of Monument Mountain to the wilderness of October Mountain State Forest, winter hikers can find adventures suited to every skill level. With proper preparation, respect for the environment, and awareness of winter conditions, the Berkshire trails provide memorable winter hiking experiences that showcase the best of Western Massachusetts’ natural heritage.
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