Top Winter Hiking Trails in New England

Best Hiking Trails in New England

The best part about hiking in New England? The sheer diversity. Stroll along the rugged Maine coast, scramble up a sheer cliff on iron rungs, follow a stream to a gorge-carving waterfall or huff-and-puff to the top of New England’s highest peak where the weather is notoriously wild.

Two classic trails are always a good bet for exploration: the 273-mile Long Trail, a mountainous corridor running the length of Vermont from Massachusetts to Canada, and the 2179-mile Appalachian Trail (AT), which blazes through Connecticut, Massachusetts, Vermont, New Hampshire, and Maine.

But if you’re looking for other hikes that aren’t quite so long or so famous, these are some of the best spots in New England, from the Green Mountains of Vermont to the White Mountains of New Hampshire to the summit of Mt. Katahdin.

Mount Monadnock, New Hampshire

Best hike for those looking for a workout
4.2 miles (6.8 km) roundtrip, 4-5 hours, strenuous

Nature lover Henry David Thoreau climbed New Hampshire’s Mount Monadnock for the first time in 1858. He enjoyed it so much he returned two years later to tackle it again. Thoreau’s not the only person to enjoy the hike to the top of this 3165 ft peak, which is climbed by more than 100,000 people every year.

Monadnock denotes “special” or “unique” in Abenaki, reflecting its isolated prominence. The most direct path to the summit is the steep and rocky White Dot Trail. The summit offers a breezy rock pile perfect for picnics and stunning views. For variety, return via the less steep White Cross Trail.

Ladder Trails, Maine

Best hike for experienced hikers
1 to 4.3 miles roundtrip; strenuous

One notable highlight is the short but treacherous Beehive Trail, featuring iron rungs that climb boulders and steep cliffs. The Beehive ends at the 520 ft summit of a granite dome, providing superb views of Sand Beach below. More challenging is the Precipice Trail, where ladders climb the steep Champlain Mountain.

Bridges and more ladders help hikers ascend a sheer cliff on the Jordan Cliffs Trail, which summits the 1194 ft Penobscot Mountain. Alternatively, for a less crowded experience, visit the Beech Cliff Trail near Echo Lake.

Note: The Precipice, Jordan Cliffs, and Beech Cliff Trails may close from mid-March to mid-August during peregrine falcon nesting season.

Mount Washington, New Hampshire

Best hike for the highly trained
8.4 miles roundtrip, 6-8 hours, extremely strenuous

The hike to the summit of the highest mountain in New England is a must for adventurous souls. However, preparation is key. This 6288 ft summit, known as “The Rock Pile”, sees some of the most extreme weather conditions in the US, with hurricane-force winds frequenting the area.

The popular Tuckerman Trail is a strenuous ascent that culminates with a rocky headwall and barren cone. Be aware—many have faced challenges due to unpredictable weather. Before departing, ensure that you check the weather at the Pinkham Notch Visitor Center.

Bash Bish Falls, Massachusetts

Best hike for artists
2 miles roundtrip, 40-60 minutes, easy to moderate

Located near the New York state line, Bash Bish Falls is Massachusetts’ tallest waterfall. The water pours down a series of gorges and drops as a picture-perfect double waterfall, greatly admired by landscape painters.

A short steep trail leads directly to the falls from Massachusetts, while a gentler path can be accessed from New York. To get to the Taconic Mountains, take MA 23 west to South Egremont, then drive to the falls’ parking area.

Mount Mansfield, Vermont

Best hike for extraordinary views
3 to more than 6 miles roundtrip; half day; strenuous

Mount Mansfield is Vermont’s highest peak in the Green Mountains, offering panoramic views from Lake Champlain to New Hampshire’s Mount Washington. The summit’s ridgeline resembles the profile of a human face, and several trails make for a versatile hiking experience.

The rocky Sunset Ridge Trail provides stunning views of the surrounding landscape. It’s essential to stay on the designated paths and avoid damaging the delicate alpine tundra.

Sabbaday Falls, New Hampshire

Best hike for all experience levels
0.4 miles roundtrip, 20 minutes to 1 hour, easy

The hike to Sabbaday Falls, located along the Kancamagus Highway, offers a glimpse of a gorge waterfall cascading through granite walls into serene pools. The area is easily accessible and includes overlooks with captivating views.

According to legend, road workers left their tools near the falls, never to return. The trail is also handicapped-accessible.

Cutler Coast, Maine

Best hike to avoid the crowds
9 miles roundtrip, 7 hours if you complete the full loop, strenuous

This little-known reserve near Cutler features hiking trails surrounded by stunning coastal scenery. It’s perfect for those wishing to escape the crowds of Acadia National Park while still enjoying breathtaking views.

The well-marked trail leads to the shoreline and beyond, taking approximately seven hours to hike the complete loop. Parking is available a few miles northeast of Cutler.

Mount Greylock, Massachusetts

Best hike for nature writers
8.2 miles roundtrip, 6 hours, strenuous

Mount Greylock, the highest peak in Massachusetts, has inspired many nature writers. The summit, accessible via the Appalachian Trail, provides incredible views. Adventurous hikers can explore the Hopper Trail to witness waterfalls and old-growth forests.

Should the War Memorial Tower be open, the 360-degree views include sights from Massachusetts to neighboring states.

Coastal Trails, Maine

Best hike for those who don’t mind getting a little wet
Marginal Way – 1 mile; Ocean Path – 2.2 miles, 30 minutes to 1.5 hours, easy

The Maine coastline is rugged and dotted with scenic features such as lighthouses. The paved Marginal Way in Ogunquit offers a lovely stroll, while the Ocean Path in Acadia National Park offers a more natural experience, complete with views of Thunder Hole.

West Rattlesnake Trail, New Hampshire

Best hike for those with limited time
1.8 miles round-trip, 1-2 hours, easy

The West Rattlesnake Mountain trail offers a short yet rewarding hike. After a brief ascent, hikers are rewarded with stunning views of Squam Lake and its surroundings.

Parking is available nearby, making it convenient for families seeking a quick getaway.

Cadillac Mountain, Maine

Best hike to watch the sun rise (or set)
4.5 miles roundtrip, 2-4 hours, strenuous

Cadillac Mountain in Acadia National Park is the perfect spot for early risers hoping to catch the first sunrise in the USA. Multiple trails lead to the top, with the Cadillac North Ridge offering the easiest access.

Hut-to-Hut Hiking in the White Mountains, New Hampshire

Best hike for adventurers
1.6 to 4.6 miles one-way; 1.25 to 3.5 hours, moderate to strenuous

Day hiking between the eight huts maintained by the Appalachian Mountain Club in the White Mountains offers delicious meals and splendid views—making for a truly enjoyable outdoor adventure. Each hut along the Appalachian Trail provides unique experiences and a comfortable refuge.

Mount Katahdin, Maine

Best hike for scrambling
3-5 miles roundtrip, 8-12 hours, strenuous

As the endpoint of the Appalachian Trail, Mt. Katahdin is a challenging yet rewarding destination. With trails leading from various campgrounds, expect to encounter beautiful scenery and the need for some scrambling.

The Hunt Trail is the most popular route, while the Helon Taylor trail offers a technical challenge for experienced hikers.

Arathusa Falls Trail, New Hampshire

Best hike for photographers
2-5 miles, 3 hours, moderate to difficult

The Arethusa Falls are a highlight of Crawford Notch, showcasing stunning natural beauty against a backdrop of history. The trail features lush woods and magnificent views, ideal for photography enthusiasts.

What You Should Know Before Hiking in New England

Be mindful of seasonal black flies, which peak between mid-May and mid-June. Some recreation areas might charge an entrance fee, so it’s a good idea to check before your visit.

Additional Resources:

Appalachian Trail Conservancy: Offers trail alerts and hiking tips.

Green Mountain Club: Maintains the Long Trail and provides trail news and camping information.

This article was first published Apr 27, 2016 and updated Nov 12, 2021.

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