Hiking

At the southernmost point of the Berkshires, near the Connecticut border, you’ll find Bartholomew’s Cobble. Walking on the Ledges Trail, the Housatonic River snakes through dairy farms on the left while eroding limestone and quartzite rocks form the cobble to your right. Take a slight detour at Corbin’s Neck to get a closer view of the river and the cows resting on its banks. Then continue on the Tulip Tree Trail to stroll uphill through a forest of tall hemlocks before reaching a clearing. At a short summit, take advantage of the bench to sit and take in the views of Mount Everett and Mount Race, part of the Appalachian Trail. 

Climbing the broad-shouldered peak Henry David Thoreau called a “sublime mass,” Mt. Monadnock, is a rite of passage for many New England children. Just over the border of Massachusetts in southern New Hampshire, Monadnock is less than a two-hour drive from Boston. Its accessibility and locale, smack dab in the center of New England, has made it one of the two most popular mountain ascents in the world going toe-to-toe with Japan’s Mount Fuji. Late April, early May, when the black flies have yet to arrive and the snow is gone, is the ideal time to bag this 3,165-foot peak. Head up the White Dot trail, one of the steepest ascents, but also one that rewards with you with incredible vistas in a very short time. Above treeline, the forest recedes to form open ledges covered with low-lying shrubs like mountain cranberry bushes. This gives you ample opportunity to rest and peer down at the soft blanket of treetops, small towns with their requisite white steeples, a smattering of lakes and ponds, and farms that fan out to anonymous ridges. Soon you’ll reach the summit, where Thoreau watched in dismay as his fellow mid-19th century trampers inscribed their names in rock. You can still spot names like “T.S. Spaulding, 1853” clearly etched in the stone. Hopefully you bagged a lunch so you can sit back, relax, and savor the views. 

Knowing that their guests like to play hard and then relish their physical accomplishments over an exceptional meal, many active travel operators in the past decade have invited well-known chefs to join them. Ciclismo Classico, best known for their biking and hiking trips throughout Italy, has teamed up with talented Boston chef, Dante de Magistris, chef at Il Casale and Dante to present an exceptional itinerary along the Amalfi Coast September 17-23. Hike amidst the cliffs of Positano, ferry over to Capri to walk secluded seaside towns, and then dine on private meals prepared by Chef Dante. He’ll also provide picnic lunches, offer cooking lessons, and invite guests into his family’s home. 

Devastated by Tropical Storm Erika in late August, the island of Dominica is bouncing back and needs your support. All you do is travel there and hike its lush interior to understand the allure. Around every bend is another raging waterfall, a serene swimming hole nestled in the thick bush, or a hidden hot springs to rest your weary body after a day in the outdoors. Ken’s Hinterland Adventure Tours will take guide you on a 7-hour round-trip hike inside Morne Trois Pitons National Park to the crater known as Boiling Lake. You’ll hike through a dense forest of tall gommier trees, staring at the iridescent purple-throated hummingbirds as they keep you company. Relax your muscles afterwards in the natural hot spring at Papillote Wilderness Retreat. Owner Anne Jno Baptiste first came to the island from the States in 1961. Eight years later, she bought a 7-acre chunk of land enveloped by the rainforest that she would cultivate into a flower-rich botanical garden and one of the Caribbean’s first eco-resorts, using Dominica’s wealth of fruits and vegetables for her meals. 

Acadia National Park turns 100 in 2016. So if you need a good excuse to get here, their centennial should do the trick. But why wait? September and October, when the crowds are gone along with the black flies and mosquitoes is an ideal time to experience this breathtaking mix of mountains and sea. I always tell my friends in the Boston area to wake up early and try to leave by 7:30 am so you can arrive just in time for lunch. Grab your National Park vehicle pass at the Thompson Island Visitors Center and continue south on Route 102 bypassing the far better known Bar Harbor for now and heading straight for the quintessential Maine coastal village of Southwest Harbor. Turn left on Clark Point Road and drive to the end to reach one of my favorite lobster-in-the-rough joints in the state, Beal’s Lobster Pier. 

Maine’s midcoast mountains reward hikers with views of the Atlantic, picturesque harbors, and three-masted schooners sailing on open waters—all for an hour or two of effort. The Maiden Cliff Trail strolls through hemlocks until it comes to a junction at the half-mile mark. Turn right onto Ridge Trail, and the ledges open up onto Megunticook Lake. The view only gets better when you turn left at the Scenic Trail and continue to the summit. Follow the white blazes, and you’ll find a huge, white cross. This marks the spot where 11-year-old Elenora French plunged to her death on May 7, 1864. She was running to catch her hat. It might be the fastest way down, but not recommended. To get to the trailhead from Camden, take Route 52 West 3 miles from the intersection of Route 1. There will be a small parking area on the right-hand side of the road just before Route 52 borders the lake.

Dominica’s volcanoes might be dormant yet there’s still fire in the belly of this island. The Valley of Desolation was just one of the highlights on a 7-hour round-trip hike inside Morne Trois Pitons National Park. Our guide, Kent, led my friend and me over muddy trails through a dense forest of tall gommier trees, used to make dugout canoes for 20 to 30 paddlers, and past the massive trunks of the banyan-like chatagnier trees, some more than 300 years old. As we made our ascent out of the darkness of the rainforest canopy, purple-throated hummingbirds kept us company as they stuck their heads into the tubular red heliconia flowers.