Convince Bostonians They Like Hiking with These Seven Hikes

Mount Chocorua offers fine views all along the trail.

September is by far the best time to go hiking in New England. The bugs are (mostly) dead, the skies are (generally) blue, and the air is just cool and crisp enough that your 3,000-foot ascent is no longer going to turn you into a dehydrated, sweaty mess. It’s the perfect time to climb mountains — and the perfect time to get the uninitiated hooked on hiking.

But many people trying to lure their friends and relations into the joys of hiking make a critical tactical error: they either aim too high, dragging their beloved couch potato on a death march to their favorite spectacular summit, or they aim too low, giving in to the newbie’s requests that the hike not be too distant, too long, or too steep. In the first case, the would-be peakbagger is too traumatized to attempt a second hike (if they even successfully complete the first), and in the second, the outing is too boring to ever inspire them to make the effort again.

So here are my six Goldilocks-perfect, “just right,” hook-a-rookie hikes within 2.5 hours of Boston. (Note: all of these are in New Hampshire; I don’t think there’s much great hiking in Mass or Connecticut within two hours of Boston. But I’m happy to be persuaded otherwise!) I’ve also included recommended eateries, since one way to ruin someone’s first hike is to not feed them enough.

The trail to Lonesome Lake is a crowd-pleaser.

1. Lonesome Lake: 5.2 miles round-trip, elevation gain 1,200 feet, 2 hours from Boston.

A number of attractive and moderately inclined trails lead up to beautiful Lonesome Lake and Lonesome Lake Hut, where you can buy a brownie from the “croo” or just use the restrooms before heading back down the trail. My favorite is the Basin-Cascades Trail, which begins just off of I-93 in Franconia Notch State Park, at a remarkable glacial pothole (the so-called “Basin”) and ascends along Cascade Brook past a number of waterfalls.

Recommended eating: Load up on piping hot flapjacks before you set out at Polly’s Pancake Parlor. Call up to an hour ahead of time to get your names on the waiting list, so you don’t have to delay your hike.

2. Old Bridle Path to Greenleaf Hut: 5.8 miles round-trip, elevation gain 2,450 feet, 2 hours from Boston.

Bridle paths were originally cleared for horses, and so make up some of the more reasonable climbs in the whites. The advantage of this trail, which also leaves from Franconia Notch State Park, is that it will give you ample opportunity to stop and admire the views of the valley below and of the peaks above as you ascend. You can either turn around once you get to Greenleaf Hut or, if your legs aren’t too tired, continue an additional 1.1 miles (and additional 1,000 feet) to the summit of Mt. Lafayette, a 5-thousand footer with spectacular views.

Recommended eating: The food in the Lincoln area is not spectacular, but the Gypsy Cafe is a popular spot for creative and reasonably tasty offerings.

3. Mount Moosilauke: 7.5 miles round-trip, elevation gain 2,450 feet, 2.5 hours from Boston.

They call this mountain “the gentle giant.” Although it’s another five-thousand-footer, the grades are moderate, the trails are wide, there’s a lovely hut at the bottom (Moosilauke Ravine Lodge), and the summit offers one of the finest 360-degree views in New England, as well as an alpine-zone meadow bestrewn with wildflowers. My preferred route is up Gorge Brook to the summit, down the Old Carriage Road (which does what it says on the tin and is quite a nice, wide, gently sloping trail), and back to your starting point via the Snapper Trail.

Recommended eating: Grab some beers and pub fare after the hike at the Woodstock Inn and Brewery in Woodstock, NH.

Fall foliage from the top of Mount Whiteface

4. Mount Whiteface: 8.4 miles round trip, elevation gain 2,900 feet, 2.5 hours from Boston.

The Blueberry Ledge Trail begins just northwest of the townlet of Wonalancet. To be honest, one of my favorite parts of hiking Whiteface is the drive up through Ashland, Holderness, and Squam Lake to the trailhead. After a beautiful drive past the farms of rural New Hampshire, you find yourself in Ferncroft, park in a field, and head up the trail. You don’t have to wait for the summit of 4,020-foot Whiteface to start enjoying beautiful views of the Granite State’s lakes. The last few feet to the summit is a rocky scramble, but everything before there is straightforward enough (especially if it’s dry).

Recommended eating: Either find any scenic spot to stop on your way from Ferncroft back to Ashland (where there’s a nice Common Man, if that’s your style), or break your trip back down at the Tilt’n Diner in Tilton, NH.

5. The Welch-Dickey Loop Trail, 4.5 miles round-trip, elevation gain 1,650 feet, 2 hours from Boston.

If there’s one downside to the trails on this list so far, it’s that so many of them are out-and-back trails, which can often be frustrating for both new and experienced hikers. The Welch-Dickey Loop is, yes, a loop trail. While you never get very high, you do see great views from the exposed ledges of mounts Welch and Dickey. Just don’t try this in the rain; the ledges get slippery when wet, and there’s not a lot of cover on top either.

Recommended eating: This isn’t a very long hike, so I’d recommend you tell your hunger to hold on and break up the drive by stopping off in Manchester, where you can eat at the fantastic Republic Cafe & Bistro.

6. Mount Monadnock, roughly 4.5 miles round-trip, elevation gain 1,800 feet, 1 hour 15 min from Boston.

You know, there’s nothing wrong with this little mountain. For the proximity to Boston, it almost feels like a “real” hike. You’ve got a nice view at the top, and the drive out along 119 is rather pretty. But the popular White Dot/White Cross loop will be jam-packed on any reasonably temperate weekend day, and I personally find the steep ascent up the White Dot trail somewhat monotonously steep and rocky. But if you want a more serious hike than the Fells, Blue Hills, or Wachusett can offer, and you don’t want to drive over two hours, this is pretty much it. (Even the Berkshires are further than that.)

Recommended eating: Groton, MA has two great spots at opposite ends of the foodie spectrum. If you’re not feeling sweatily unpresentable, splurge on steaks at the Gibbet Hill Grill. If you’re feeling sweaty and broke, get delicious comfort food and ice cream at Johnson’s Drive In.

7. Mount Chocorua: 8.4 miles round-trip, elevation gain 2,700 feet, 2 hours and 30 minutes from Boston.

For the purposes of the calculations above, I’m assuming you’re taking the Piper Trail up to the summit and back. It’s one of the most popular trails in the White Mountains, and you’ll have company — but the 360-degree view at the top is worth it. Photographers also love Chocorua because of its dramatic rocky summit cone and its picturesque location next to a lake. Despite the length of this trail, it’s not a particularly strenuous 8 miles (as far as these mountains go). However, note that the summit is totally exposed, and in bad weather has a nasty habit of attracting lightning. But if the day is clear and sunny, you’ll be rewarded with some of the best views in the Whites.

Recommended eating: Stop in Portsmouth, NH, on the way back for a beer sampler at the Portsmouth Brewery  — and any of the delicious dishes they cook with their beer.

7.5. Zealand Falls Hut: 5.6 miles round-trip, elevation gain 1,300 feet, 3 hours from Boston.

This is quite a long drive from Boston, so I initially bumped it from the list, but it’s a great beginner trail nonetheless: beautiful, but relaxed. A relatively flat (until the very end) walk along Zealand Trail will bring you alongside beaver ponds, through woodlands, over the occasional boardwalk, past wildlife, and up to the Zealand Falls Hut, which itself is situated next to the massive falls. Yes, they’re eponymous. And they’re spectacular.

Recommended eating: Skip 93 and drive back south along NH 16, a scenic highway that will take you past the Moat Mountain Smokehouse and Brewing Co. Get anything with BBQ sauce on it, and be sure to try their beer sampler.

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A quick word on breakfast: if you’re going past Exit 28 on 93 (which you would be for everything except Whiteface, Chocorua, and Monadnock) a great place to stop for coffee and a breakfast sandwich to go is Mad River Coffee Roasters. They roast their own beans on-site, and their egg-and-bagel sandwiches are made fresh to order. It’s a great start to any hike — and the owners are putting up a valiant fight against the Dunkin Donuts that recently opened across the street.

A quick word on safety and fun: Newbies never think they’re going to need *that* much water. They will. Just because you can hike 17 miles doesn’t mean you won’t faint at the end of it and ruin everyone’s day (I learned this the hard way). So make sure you carry at least 2 liters of water (plus a liter of gatorade for longer hikes) and plenty of food. On a recent hike, we each took trail mix, energy bars, a sandwich, a banana, and two hard-boiled eggs, as well as three liters of liquid, and we were in fine fettle on our way down. (There’s also a great bagel-and-sandwich shop in Lincoln if you’re leaving Boston too early to reasonably be able to make yourself a square lunch. It’s called the White Mountain Bagel Co and is right off the highway. I find bagel sandwiches hold up better in the backpack than bread sandwiches do.)

Leave yourself plenty of daylight to get down the mountain, or instead of enjoying your hard-earned beer you’ll be scrambling down in the dark trying to use your dying cell phone as a flashlight.

And don’t wear cotton, if you can help it. Instead, wear wicking athletic gear and bring fleece or wool (which both stay warm when wet) and a good raincoat in case the weather turns.

And regardless of whether it’s your ankle or the weather that turns in your first few minutes on the trail, never, ever say: “Well, we came all this way, we have to hike it.” Not true, actually. The mountains will still be there next year, and there’s absolutely nothing wrong with deciding to pack it in and spend a little more time curled up by the fire with your beer and your book.

Hike safe, have fun, and let us know where you end up!