Top 10 Winter Hiking Trails in New England
Plus what we wear, how we prep, and what we listen to along the way.
At The Merrimack Company, winter doesn't mean staying inside. It means slowing down, layering smarter, and embracing the quieter version of the outdoors that New England does so well.
Winter hiking isn't about conquering the trail, its about moving intentionally, respecting the conditions and choosing pieces that keep you comfortable without overcomplicating things. With the right preparation (and the right layers), winter can easily become one of the most rewarding seasons to get outside.
Here are 10 of our favorite winter hikes across New England, plus what we bring with us and the playlist we've been building for cold weather days on the trail.
Top 10 Winter Hiking Trails in New England
Mount Monadnock (New Hampshire)
Winter Difficulty: Difficult
A New England classic with fewer crowds in winter. Expect icy rock slabs and big summit views. Traction is essential.
Franconia Falls Trail (New Hampshire)
Winter Difficulty: Moderate
A longer but mostly flat hike that's perfect for steady winter miles. Snow covered trees and frozen waterfalls make it worth the distance.
Welch & Dickey Loop (New Hampshire)
Winter Difficulty: Difficult
Short, steep and exposed. This loop offers incredible views but demands respect in the winter conditions.
Mount Greylock (Massachusetts)
Winter Difficulty: Difficult
The highest point in Massachusetts feels especially quiet in winter. Cold temperatures and changing weather make preparation key.
Bash Bish Falls (Massachusetts)
Winter Difficulty: Moderate
A relatively short hike with a big payoff. Winter ice near the falls can be slippery but the scenery is unmatched.
Kancamagus Highway Trails (New Hampshire)
Winter Difficulty: Moderate but Varies
A collection of accessible trailheads with varying difficulty. Great for choosing your adventure based on the day's conditions.
Jordan Pond Path (Maine)
Winter Difficulty: Easy
A mostly flat loop with incredible winter stillness. Snow covered carriage roads make this a peaceful cold weather option.
Mount Willard (New Hampshire)
Winter Difficulty: Moderate
One of the best effort to reward hikes in the Whites. A steady climb leads to sweeping valley views.
Mount Agamenticus (Maine)
Winter Difficulty: Easy-Moderate
Short trails with coastal views. Often accessible year round and ideal for a quick winter outing.
World's End (Massachusetts)
Winter Difficulty: Easy
Rolling hills, wide paths and ocean views make this a perfect winter walk when you want to get outside without full alpine conditions.
What We Wear on Winter Trails
Winter hiking is about layering intentionally. We keep it simple and rely on pieces that regulate temperature, move with us and transition easily from trail to everyday life.
Unisex Heavyweight Thermal
This is our foundation layer. We wear the Unisex Heavyweight Thermal directly against the skin for warmth without bulk. It traps heat on cold mornings but breathes enough for uphill climbs, making it ideal for winter hikes where conditions change quickly.
Merino Wool and Cashmere Beanie
No winter hike starts without a beanie. Our Merino Wool and Cashmere Beanie keeps us warm even when damp, regulates temperature and packs easily into a pocket when we heat up. It's one of those pieces that earns its place season after season.
Travel Dog Bowl
Winter hikes are better with a trail companion. Or as we like to call them, an Adventure Buddy. The Travel Dog Bowl is durable enough for the trail and easy to clean after. Lightweight, packable and easy to clip onto a bag, it makes quick breaks simple. Whether you are stopping at a lookout, trail junction or back at the car, it will quickly become one of those essentials you'll never hike without again.
Introducing The Merrimack Company Adventure Playlist
What you listen to matters, especially in winter. We're building The Merrimack Company Adventure Playlist. Perfect listening for setting your intentions on the drive, quiet miles in the crunch of the snow, steady climbs and moments when the trail feels almost meditative.
Think:
- Grounded, steady rhythms
- Indie and instrumental tracks that don't overpower nature
- Music that keeps you moving when it's cold and quiet as well as when the sun is shining
This playlist is meant to support the experience, not distract from it.
Listen to The Merrimack Company Adventure Playlist
A Few Hiking Reminders
- Always check weather and trail conditions
- Bring traction and know when to turn back
- Start earlier than you think you need to
- Choose layers you can rely on, not just carry
If you haven't already, download The Merrimack Company Adventure Playlist. It's exactly what we use when out on the trails.
Final Thoughts
Winter strips things down. Fewer people, quieter trail and a slower pace. With the right mindset and gear that works with you instead of against you, it becomes one of the most rewarding seasons to be outside.
Wherever you're hiking this winter, move intentionally, layer smart, enjoy the stillness, be responsible and......
Stay Adventurous
- The Merrimack Company
Share your Adventure Tips with the Community
What are your favorite winter trails? Your go to adventure song? Must have items for the trail? Comment below