New England

33 Favorite New England Hikes | The Great Outdoors

When the time is right to hit the trail, these hikes deserve a spot on your to-do list. A guide to Yankee editors’ favorite hikes in every New England state.

By Yankee Editors

Jul 27 2021


Established in 1819, New Hampshire’s Crawford Path winds more than eight miles through the southern Presidentials on the way to the summit of Mount Washington.

Photo Credit : Chris Shane
This year has been a trying one, to say the least. And whether this summer finds us still staying close to home or venturing out into the wider world, we want to share with you some of our region’s many beautiful rambles, scrambles, and uphill climbs that we have honored with Best of New England awards or showcased on In years past, these nature experiences have nourished our souls, and we have no doubt they will do so again, when the time is right. These New England hikes are, in a very real sense, our paths to recovery. TRAVEL NOTE:In light of public health concerns, towns and parks may have closed or reduced access to their trails. Hikers should check with them directly before making any travel plans, and always follow social distancing guidelines on the trail.
Established in 1819, New Hampshire’s Crawford Path winds more than eight miles through the southern Presidentials on the way to the summit of Mount Washington.
Photo Credit : Chris Shane

33 Favorite Hikes in Every New England State

New Hampshire Hikes

Crawford Path, Carroll: Best Epic Hike. More than two centuries after it was created, the nation’s oldest continuously maintained hiking trail, the Crawford Path, still delivers the rugged but accessible adventure that its founders envisioned. Running 8.2 miles (one way), it concentrates the White Mountains experience: steep ascents, sun-soaked plateaus, boulder-strewn peaks. Challenging climbs give way to flat stretches where hikers can linger and take in those panoramics before making the push to reach Mount Washington, the Northeast’s highest peak.

Mount Monadnock, Jaffrey:Best Day Hike. It’s a National Natural Landmark and one of the most-climbed mountains in the world for a reason. Though you can take your pick from any of its beautiful trails, we recommend that first-time Monadnock hikers—or even first-time hikers, which is often the case at this mountain—head up to the top via the White Dot Trail and descend by way of the White Cross Trail (about 4.2 miles up and back). At the bald summit, surrounded by thousands of acres of protected highlands, you can look out toward Boston, nearly 100 miles away.

Mount Willard Trail, Hart’s Location: Best Beginner Hike. If the thought of mountain climbing makes you sweat long before leaving your car, wipe your brow and give Mount Willard a try. In less than an hour after setting out on this 2.8-mile round-trip hike, you’ll make it to the peak, where stunning views of Crawford Notch stand before you.

Gregg Trail, Greenfield:Best Wheelchair-Accessible Trail. Hikers of all abilities can look for wild turkeys and patches of wild blueberries along this 1.6-mile path (round-trip) ascending to the Knoll, with an observation deck overlooking a panorama that includes Mount Monadnock. The Gregg Trail and its neighbor, the 2-mile loop Dutton Brook Trail, are said to be the nation’s longest accessible trails in a mountainside environment.

Flume Gorge Trail, Lincoln: Best Family Hike. One of New Hampshire’s most beloved natural attractions, the Flume Gorge is the main feature of an easy 2-mile walk through piney woods over hilly terrain. The setting is certainly dramatic: 90-foot cliffs, cascading falls, and the cool dampness of a primordial forest. But there’s also something appealingly Swiss Family Robinson–like about the network of cliff-hugging boardwalks clinging to the walls of this deep granite beauty at the base of Mount Liberty.

Mount KearsaRge, Warner: Best Short Hike. This 1-mile loop begins in Rollins State Park on an old carriage road that ascends 300 vertical feet in half a mile, and from there it’s a quick scramble to the top of Mount Kearsarge, with its endless views of villages, lakes, and patchwork pastures.

Connecticut Hikes

Bear Mountain Trail, Salisbury: Best Day Hike. If you’re looking for the ultimate perspective for leaf peeping, heading to Connecticut’s highest peak (2,316 feet) is a good bet. This relatively steep 6-mile loop hike, which starts from the Undermountain Trail parking lot, eventually rewards hikers with one of the prettiest vistas in the state, with mountain views to the north, south, and west, and lake views to the east. The route even follows a section of the legendary Appalachian Trail.

Talcott Mountain Yellow Trail, Simsbury: Best Family Hike. While Talcott Mountain State Park has other routes to the top, the 2.5-mile Yellow Trail loop is a popular and family-friendly way to reach the summit and its 165-foot Heublein Tower. Prepare to pause often to admire the ever-expanding views of the verdant Farmington Valley; to the southeast, Hartford’s skyline juts up from the landscape, looking regal and remote. Kids will love climbing the tower, built as a summer residence in 1914.

Sleeping Giant Tower Trail, Hamden:Best Easy Hike with Big Views. This trail starts at the picnic area across from Quinnipiac University and is a 1.6-mile hike one way to the summit of Mount Carmel, where you will find a beautiful stone observation tower that offers a fantastic vantage overlooking Long Island Sound and New Haven. A unique feature of this trail is the stone path, so plan your footwear accordingly. The trail is a part of Sleeping Giant State Park, named for the two miles of mountaintop that some say resemble just that: a sleeping giant.

Haystack Tower Loop Trail, Norfolk:Best Short Hike. The view from the Rapunzel-esque three-story stone tower atop Haystack Mountain is worth the half hour or so of exertion it takes to scramble to the summit on this 1.8-mile loop trail. From the parking area, the short, steep hike is doable for most abilities. At 1,716 feet above sea level, the landscape seems to gleam and glow. Write a fairy-tale ending by packing a picnic.

Jessie Gerard Trail, Barkhamsted: Best Quiet Fall Hike. Located in the 3,000-acre-plus Peoples State Forest, the Jessie Gerard Trail is a moderate 2.6-mile loop featuring stone steps, challenging climbs, rocky cliffs, gorges, dense forest, and, ultimately, unforgettable fall foliage photo ops from the Grand Vista overlook. Travel farther north and take in even more incredible views from Chaugham Lookout.

Maine Hikes

Mount Katahdin, Baxter State Park:Best Epic Hike. There may be no bigger Maine bucket-list item for hikers than Katahdin and its Knife Edge Trail. Measuring slightly over a mile, the Knife Edge is just one segment of a strenuous summit climb that you can piece together out of the mountain’s network of trails. But oh, is it ever a memorable one: Some spots on this ridge traverse are as narrow as four feet, with 2,000-foot drops on either side. And at the end, the 5,267-foot Baxter Peak, with out-of-this-world views.

Bold Coast Trail, Cutler:Best Down East Hike. Keep it short or go the distance on this easy-to-moderate jaunt, set on Cutler Coast Public Reserved Land and winding through forests and wetlands to the wild and spectacular Bold Coast cliffs. Sightings of whales and porpoises are possible. Options include the relatively easy 2.8-mile out-and-back hike to the coast and 5- and 10-mile loops.

Mount Agamenticus, York:Best Wheelchair-Accessible Trail. Most visitors to Maine’s south coast head straight for the beach, and rightly so. But a detour to Mount Agamenticus, just a stone’s throw from the sandy playgrounds of Ogunquit and Wells, will reward you with one of the best “bang for your buck” hikes in the Pine Tree State. Of the trail options here, the universal-access Big A Trail is a 1-mile loop ideal for families, offering a wide path and benches for resting, and there’s a nature center at the top.

Moxie Falls, The Forks:Best Waterfall Hike. One of New England’s highest and most dramatic waterfalls, with a single vertical drop of nearly 90 feet in addition to other plunges and pools, Moxie delivers a hefty reward for modest effort. The 1.2-mile (round-trip) trail begins on a wide swath through the woods, and then ascends via boardwalks and steps to the falls.

Ship Harbor Trail, Acadia National Park: Best Short Hike. Pick up a trail guide at the park visitors’ center and bring a picnic. This gentle 1.3-mile figure-eight hike passes through varied ecosystems, from moss-laden woods to pink granite ledges, and provides wonderful views of Acadia’s rocky coast.

Rattlesnake Mountain, Raymond: Best Family Hike. Don’t be deterred by the ominous reptilian name! Rattlesnake Mountain via the Bri-Mar Trail is a moderate 2.4-mile out-and-back hike that—while steep in some places—is dog-friendly and kid-appropriate. Look for a great shot of Panther Pond just half a mile in.

Rhode Island Hikes

Black Point, Narragansett:Best Beachside Hike. Although Narragansett is best known for its sandy beaches, this 2.1-mile out-and-back stretch is more Maine than Rhode Island, with layers of rocks to clamber on, fish from, or hike beside. A former Narragansett Indian path, Black Point offers intriguing plants along the way, views of Point Judith Light, and mysterious stone ruins.

Clay Head Trail, Block Island: Best Island Hike. First, this 3.5-mile out-and-back trail in Clay Head Preserve descends into a marshy area; then it climbs into a sunny meadow, all the while providing a low, rumbling thunder-like soundtrack from the crashing surf below. And then suddenly you’re there: at the edge of a high, sandy bluff, gazing across sparkling water to what in Block Island–speak is called “America,” or mainland Rhode Island.

A Rhode Island go-to for hikers of all ages, Block Island’s Clay Head Trail is set on a 150-acre nature preserve and leads to spectacular ocean views.
Photo Credit : Nat Rea

Long Pond Woods Trail, Hopkinton: Best Hike with a View. Scramble over glacier-dumped boulders and under mountain laurel on this roughly 4-mile out-and-back path. The expansive vista from high bluffs above Ell and Long ponds is truly breathtaking at this National Natural Landmark and wildlife refuge. And if the scenery looks familiar, it might be because part of the 2012 movie Moonrise Kingdom was filmed here.

Norman Bird Sanctuary, Middletown:Best Nature Hike. With 300-plus acres of nature preserve and seven miles of trails—including a wheelchair-accessible path down to a viewing platform by the pond—hikers are treated to all types of terrain, from open fields to forests. Come armed with binoculars to spot swallows and sparrows, not to mention eye-popping panoramas of the Sakonnet River and the ocean.

Rome Point Trail, Saunderstown: Best Family Hike. This 2.4-mile loop in the John H. Chafee Nature Preserve is perfect for hikers and walkers of all skill levels (and their leashed pups). The trail starts inland and leads out to the bay, and the constant scenery change makes for an exciting quick trip. As a result, this trail—also known as the “seal hike” for its view of seals in the bay—is very popular during the summer, so to beat the crowds, make plans to go in the fall.

Vermont Hikes

Camel’s Hump, Duxbury & Huntington: Best Epic Hike. The distinctive mass of rock atop this 4,083-foot peak can be seen in the distance across northern Vermont. To stand atop that mighty summit, you’ll need two strong legs, an ample amount of water, and plenty of gorp to make it through your 6-mile round-trip journey via the Monroe Trail (which is our go-to, but other routes are available).

Butler Lodge Trail, Underhill: Best Quiet Fall Hike. There are many ways to climb Mount Mansfield, Vermont’s highest peak. For hikers who love life above the tree line, one of the lesser-traveled paths offers a straight shot to the ridge. From the trailhead on Stevensville Road in Underhill, Butler Lodge Trail warms up with a half mile through hardwoods before shooting steeply uphill. After 1.8 miles and 1,600 vertical feet, the trail arrives at its namesake structure, where you can rest before heading back down, or take some time to explore the krummholz (gnarled, windblown trees) via the Wampahoofus Trail).

Snake Mountain, Addison & Weybridge: Best Easy Hike with Big Views. Vermont’s Green Mountains may be the star attraction, but when you’re short on time and energy, you can’t beat Snake, a 1,287-foot outlier of the Taconic range that rises abruptly from the surrounding terrain to offer the state’s finest panorama of dairy lands, Lake Champlain, and the Adirondacks. Park in the lot on Mountain Road and walk less than a quarter mile to the well-marked trailhead on the left. Follow the Old Carriage Road 1.5 miles to the top, where you’ll find a cement platform from the 1870 Grand View Hotel that once stood here; now it’s a great spot for picnics.

Mount Pisgah, Westmore: Best Hike in the Kingdom. Mount Pisgah rises above the southeastern edge of Lake Willoughby, the loveliest lake in the Northeast Kingdom, not to mention the state. This roughly 4-mile round-trip via the South Trail gives you a falcon’s-eye perspective on Willoughby’s waters, along with views of the Green and White mountains. If you have the stamina, tack on the North Trail or East Trail.

Sterling Pond Trail, Jeffersonville: Best Quiet Fall Hike. This moderate trail in Smugglers’ Notch State Park is about 2.8 miles out and back, and while steep and rocky in some portions, the path is well maintained and leads to gorgeous views—and Vermont’s highest-elevation trout pond, to boot. Sterling Pond has been described as “idyllic” and is a great escape during the quieter fall months.

Massachusetts Hikes

Skyline Loop, Milton: Best Hike Near Boston. Great Blue Hill (635 feet), just south of Boston, is the highest peak in the Blue Hills Reservation and also the highest summit south of Maine that’s near the Atlantic Ocean. In just three miles round-trip, hikers can hit several summits in the Blue Hills range, including Great Blue Hill, and visit Eliot Tower and the Blue Hill Observatory. Additionally, the reservation has 125 miles of trails with a range of easy to rugged terrain, so there are plentiful opportunities to add on to or switch up your hike. (Note: If you have the stamina, the full Skyline Trail runs nine miles from start to finish.)

South Sugarloaf Trail, South Deerfield: Best Short Hike. Not to be confused with its much bigger cousin in Maine, this Sugarloaf Mountain is, for nature lovers, a literal sweet spot. The 1.4-mile loop trail to the south summit is short yet steep enough to get the endorphins going, and the 652-foot summit, crowned with an observation tower, is an unbeatable perch for gazing out over the Connecticut River, the Pelham Hills and Berkshire Hills, and the Pioneer Valley towns of Deerfield, Sunderland, and Amherst.

Stony Ledge, Williamstown: Best Easy Hike with Big Views. You can sidestep the exertion of summiting Mount Greylock, Massachusetts’s highest peak, while still reaping its visual rewards when you stride up the 1.9-mile-long unpaved Sperry Road to the Stony Ledge outlook. It offers a vertiginous 1,400-foot view into the Hopper, a steep-sided bowl notable for old-growth woods, with a majestic panorama of the Bay State’s highest peaks.

Wachusett Mountain, Princeton: Best Choose-Your-Own-Adventure Hike. Dubbed the “Observatory of Massachusetts” by Thoreau, Wachusett Mountain is the loftiest peak within a reasonable traveling distance from Boston. The versatile mountain, which is set on its namesake 3,000-acre state reservation, beckons to hikers of all levels with 17 miles of well-marked trails traversing forests and meadows, streams, and ponds. You can take the 3-mile out-and-back Harrington Trail straight to the 2,006-feet summit, or put together a loop out of any of the dozen or so marked routes.

Monument Mountain, Great Barrington:Best Quiet Fall Hike. A moderate 3-mile loop—up the Hickey Trail and back down the Indian Monument Trail—leads to a natural oasis with great views. It’s a popular route during the warmer weather months, so taking a trip during the fall often provides an escape from the typical traffic. Some areas of the trail are steep, but a few scrambles will afford you a big payoff: foliage colors seen from the summit, rippling across the Housatonic River Valley and the southern Berkshires.

Middlesex Fells Reservation, Stoneham: Best Hike for Families. With 2,575 acres spanning five towns, a range of terrain, and a no-excuses travel distance from Boston, Middlesex Fells Reservation is an ideal destination for outdoor activities of all kinds. There are a number of beautiful natural features at the Fells, including Sheepfold Meadow, a 10-acre open field, and Wright’s Tower, which looks out over the Boston Basin, plus ponds and plenty of wooded areas. Budding naturalists will love the easy, mile-long Long Pond Nature Trail, which has a nature pamphlet describing plants, animals, and geology along the way.