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Boston Trails

Boston's Top 5 Dayhikes

The best local trails, as selected by BACKPACKER Local scout Daniel Nelson.

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Beantown: city of colonial history, collegiate culture, the Red Sox, and premium access to the mighty White Mountains of New Hampshire. Boston hikers can easily go from the center of urbanity to sweeping New England summits for a day’s escape, with options ranging from waterfalls to lonely lakes to peakbagging missions. And closer to home, you’ll also find nature adventures at the nearby Middlesex Fells Reserve. 

The view from Mt. AdamsTim Sackton

1. Mt. Adams via Air Line Trail, Presidential Range, NH

Trailhead: Air Line 
Mileage: 8 (round-trip)
Drive time from Boston: 3 hours 

The Northeast isn’t exactly known for heart-stopping cliff-edge routes, but I’ve found Mt. Adams’ Durand Ridge pretty fun all the same. I love timing my climb up Air Line Trail, a ragged, 4-mile track through Mt Adams’ weathered terrain. And after a long week of classes, the 4,700-foot ascent can be the perfect challenge for my underworked calves. Aim to go on a clear, sunny day (a big ask, given the Presidential Range’s notoriously wicked weather) to snag panoramic summit views.

Tripyramid viewsDavid Smith

2. Tripyramid Trail, White Mountains, NH

Trailhead: Livermore (Waterville)
Mileage: 11.5 (round-trip)
Drive time from Boston: 2.5 hours

There are few better ways to spend a White Mountains day than by bagging the three peaks of aptly named Mt. Tripyramid. And when I say day, I really do mean the whole day – the nearly 12-mile, north-south trek takes me about seven hours. I usually start with the North Slide for its exciting rock scramble, and then keep heading south until I’ve hit all three peaks. Don’t worry about getting stranded far south of your car; after clearing the peaks, the trail loops back to Livermore Trail.

Vistas on the Glen Boulder TrailTim Sackton

3. Mt. Isolation via Glen Boulder Trail, Presidential Range, NH

Trailhead: Glen Ellis Falls
Mileage: 12 (round-trip)
Drive time from Boston: 3 hours 

Although I haven’t yet notched off all 48 peaks of New Hampshire’s 4,000-Foot Club, I can claim the one that many trail junkies save for last because it’s one of the most remote: Mt. Isolation. Looking back, I probably should have waited – my first attempt up the 4,003-foot mountain ended in failure. You might blame my midday start, or my lack of layers, or my leaky CamelBak. Or, you could learn from my mistakes and try Isolation for yourself. Start early, pack smartly, and be prepared for bone-chilling cold once you reach the top. For the well-prepared, the trip is a challenging climb with lots of above-treeline hiking and views over the southern Presidentials.

Lonesome Lakelawepw

4. North and South Kinsman Mountains

Trailhead: Lafayette Place Campground
Mileage: 9 (round-trip)
Drive time from Boston: 2 hours 

My all-time favorite winter trail (in New Hampshire’s Whites, at least) has to be my trip up North and South Kinsman. I’ve only ever hiked this trail in winter, and by the looks of it the terrain doesn’t seem that challenging come summertime. But hefty snowpack and occasional ice patches added much-needed flair to my day outdoors. Connect the Lonesome Lake, Cascade Brook, and Fishing Jimmy Trails to reach the summits. Some tips: I usually pack snacks for a nosh by the AMC’s Lonesome Lake Hut. And don’t forget snowshoes or MICROspikes if you’re hiking in winter or early spring.

Middlesex Fells ReservationSang-Min Yoon

5. Middlesex Fells Reservation

Trailhead: South Border Road parking lot
Mileage: Choose your own adventure
Drive time from Boston: 10 minutes 

So far, I’ve run through this Boston-area dayhikes list without listing a single trail in Boston. And unless the city’s Freedom Trail counts as a day hike (and it most certainly does not) I’m afraid it will stay that way. But fear not, intrepid local hikers! The Middlesex Fells, found just a few miles from the city limits, should be your day-trip go-to. I’ve visited the 2,000-plus-acre Fells reservation more times than I can count, and each time has been better than the last. Pack a book, a hammock, a pair of binoculars and a tuna fish sandwich, and spend a day exploring the Fells’ many winding paths. Here and there you may stumble upon some standout features. Once I found the lake; another time, a set of climbable boulders. If you’re feeling adventurous, try to find your way to the fire tower without using a map (hint: Keep going up!).

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