One of my favorite ways to escape the city and get some fresh air is by hiking. I got hooked on this activity when I lived in San Francisco, though New England has it’s own charm and impressive trails as well! The hikes below are short drives (within 2.5 hours) of Boston. I recommend AllTrails for specific guides and advice.
Mount Chocorua in Conway, NH
The Mount Chocorua Loop Trail is a White Mountains 9 mile trail approximately 2.5 hours from the city. The first 1.5 miles is a piece of cake and the perfect way to warm up your legs for 3 miles of steep rocks and scrambling at the summit. There are 360 degree views at the top including the show stopping Mount Washington.
Mount Monadonock in Jaffrey, NH
This is the classic New England hike. In fact, it’s one of the most climbed mountains in the world (sources vary but it’s always listed in top 3!) There are several trails ranging from the direct White Dot trail to the long and winding Pumpelly Trail. The mountain stands alone and at the top there are panoramic views of Massachusetts, New Hampshire and Vermont. Ironically I wouldn’t consider this the best view ever because the mountain is isolated from everything else, but the hike is also a right of passage.
Welch and Dickey in Thornton, NH
The Welch and Dickey Loop trail, recommended counter-clockwise, starts with an easy incline for the first mile that leads to Welch Mountain. From then on, it’s exposed ridges and smooth rock slabs to climb. The descent from Welch Mt. to the valley between the two mountains is a little steep at points, but nothing outrageous. For a 3 hour, >5 mile hike, this one packs all the punches.
Mount Washington in Bretton Woods, NH
This is a tough climb and arduous hike…no way around it! It requires more preparation as the weather could turn at the flip of a switch. The good news is that there are some epic (and distracting) views that are worthy of breaks along the way. I chose the Ammonoosuc Ravine Trail as it includes a stop at the Lakes of the Clouds Hut. At the top, the heated lodge includes a Snack Bar with (mediocre) cafeteria style food and a museum. The queue at the summit sign is often filled with road trippers and motorcyclists. And one of the best parts? The option to take the Cog Railway down the mountain. If you opt to hike down, you’ll be one of the few.
Mount Lafayette in Lincoln, NH
The Mount Lafayette Franconia Ridge Trail Loop is a ~9 mile loop and rated as difficult (it almost killed me.) A perfectly placed Greenleaf Hut is located at the junction of the Old Bridle Path and Greenleaf Trail, overlooking Eagle Lake. It is an ideal location to take a breather, enjoy a snack and mentally prepare for the final climb. On a clear day, the ridge walk between Little Haystack Mountain, Mount Lincoln, and Mount Lafayette is the hike that keeps on giving with sweeping views for miles around, including the Presidential Range and Lonesome Lake.
Basin-Cascades Trail in Lincoln, NH
“Relaxing” is the best way I have to describe the Basin Cascades path. Meanwhile, David Thoreau stood in the same place in the 1800s proclaiming the Basin as “perhaps the most remarkable curiosity of its kind in New England.” It’s a peaceful path along the river, although harder to avoid the crowds here!
West and East Rattlesnake Mountain in Holderness, NH
Old Bridle Path is a 3.1 mile easy-ish hike. The Squam Lake views at West Rattlesnake Mountain are spectacular for a small amount of work. I highly recommend this one during peak fall season.
World’s End in Hingham, MA
The World’s End 3 mile loop offers an idyllic landscape through mature oaks, maples and pines. The Boston skyline is visible across the water on clear days. Wildflowers, marshes and pastures indicate a perfect setting for a picnic before, after or during the walk.
Blue Hills in Medford, MA
The Skyline Loop is just outside of Boston and a mostly flat path of 7.6 miles. It is not that well marked and easy to veer off/ to take one of the spider web trails that stem off the main path. Nothing out of this world, but something to get your blood pumping and cool glimpses of the city along the way.
Cliff Walk in Newport, RI
The Cliff Walk is a 3.5 mile path of “history, beauty and adventure.” The path offers a behind the scenes look at the beautiful mansions, historic properties (64 private residences!) and Salve Regina University buildings. Keep an eye out for seals, dolphins and surfers! Though at first glance it may look like just a walking path, I highly recommend solid footwear as the path changes to rocks, tunnels and even has access to a couple small beaches.
And for Boston: The Harbor Walk, Castle Island and the Esplanade path are all favorites! Not so much hikes as flirtatious strolls among the trees and water. Enjoy!
