New England

27 Great New England Hikes to Tackle This Fall

For outdoors lovers, there’s no time like autumn to hit the trail. These day hikes are some of the best fall hikes in New England.

By Yankee Editors

Oct 04 2021


The payoff for an autumn trek to West Rattlesnake Mountain in Holderness, New Hampshire: sweeping views of Squam Lake tinged with fiery color.

Photo Credit : Douglas Merriam

While we’re longtime fans of the classic fall foliage drive, there’s a lot to be said for slowing things down to a few miles an hour to experience New England’s seasonal colors at their finest. The following collection of favorite foliage hikes from Yankee editors offers a little something for everyone, from challenging routes up famous peaks to gentle rambles through woodlands. And many take at least a full morning or afternoon to complete, letting you linger in some of the most scenic spots in New England at the loveliest time of year.

The payoff for an autumn trek to West Rattlesnake Mountain in Holderness, New Hampshire: sweeping views of Squam Lake tinged with fiery color.
Photo Credit : Douglas Merriam

27 Great New England Hikes to Tackle This Fall

Fall Connecticut Hikes

Bear Mountain, Salisbury:~6.5 miles. 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 loop hike, which starts from the Undermountain Trail parking lot and climbs through hardwood and conifer forest, eventually rewards hikers with one of the prettiest vistas in the state, with mountain views to the north and west, and lake views to the east. The route even follows a section of the legendary Appalachian Trail.

Mount Higby, Middlefield:~9 miles. Hike the Mattabesett Trail for some of the best views of the Quinnipiac Valley you’ll find in all of central Connecticut. While the Mattabesett Trail itself is 50 miles long, this hike up Mount Higby is less than 10 miles out and back. It features steep climbing and some rocky scrambling, and leads to ledges with beautiful overlooks. The view at the pinnacle extends almost 360 degrees, encompassing Massachusetts’s Mount Tom to Long Island Sound. You’ll find plenty of towering trees wearing their foliage finery along this well-maintained trail, marked with blue blazes.

Sleeping Giant, Hamden:~5.8 miles. The site of one of Yankee’s favorite easy fall hikes, the Tower Trail, also offers rugged and rewarding day-hike options thanks to the network of trails around Mount Carmel, a distinctive stretch of elevated terrain that resembles a giant lying in repose, giving the surrounding 1,465-acre state park its name. A favored route is the Blue/Quinnipiac Trail, which winds more than a mile up to the top of Mount Carmel, where a 1930s stone observation tower gives a bird’s-eye view of the Mill and Quinnipiac River valleys below. This is already the fourth and highest summit in a journey that hits seven small peaks in all, with many ledges for leaf peeping along the way, before returning you via the Yellow Trail to the parking

QUICK HIKE | Haystack Mountain, Norfolk:~1.8 miles.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 scenic loop trail. From the parking area, the short, steep hike is doable for most abilities. Seen from 1,716 feet above sea level, the autumn landscape seems to gleam and glow.

Fall Maine Hikes

Borestone Mountain, Elliotsville:~5.2 miles. Though most of Maine Audubon’s centers and sanctuaries are located on the coast, foliage lovers can head inland to explore Audubon’s lone North Woods outpost, the 1,639-acre Borestone Mountain Sanctuary, near the southern end of the 100-Mile Wilderness forest. The mountain has two peaks with 360-degree views that can be reached by the Base and Summit trails, plus there’s a half-mile spur trail that climbs above a series of cliffs overlooking a trio of pristine alpine ponds. Bring binoculars to drink in the color of the mature hardwood forest below—and maybe spy a moose feeding too.

Caribou Mountain, South Oxford: ~7 miles. Nothing says New England autumn vistas quite like the White Mountain National Forest, but while New Hampshire has the lion’s share of this scenic sprawl, you can find a terrific chunk of it in Maine, too, and often with much lighter crowds. The Mud Brook/Caribou loop leads through dense forest, across brooks, and past cascades, and includes a 2,000-foot elevation gain to reach Caribou’s open summit, with views of mountains, notches, the rolling Oxford Hills, and the twisting, sparkling ribbon of 10-mile-long Kezar Lake.

Mount Megunticook/Maiden Cliff, Camden:~6.5 miles. Many visitors to Camden beeline it to Mount Battie, thanks to its centrally located trailhead, handy summit-road option, and unbeatable perch overlooking the forested slopes down to the town’s lovely harbor. Still, it’s only the tip of 5,700-acre Camden Hills State Park. Dig in for a meatier day hike by tackling the park’s highest peak, Megunticook (elevation 1,385 feet), on a double loop composed mainly of the Maiden Cliff, Ridge, and Jack Williams trails, which offer rock-ledge lookouts along the way that frame everything from Penobscot Bay to Lake Megunticook to, yes, Mount Battie in foliage finery.

North Traveler Mountain, Baxter State Park: ~5.6 miles. For those who like a challenge but aren’t ready for Baxter’s superstar, Katahdin, this out-and-back segment of a longer loop trail on Maine’s highest volcanic peak, the Traveler, delivers on steepness, scrambles, and stunning vistas in less than four hours round-trip. Your destination is the North Traveler summit, and after the first lookout half a mile in, maples and birches yield to long stretches of open ridge, providing largely unobstructed views of mountains, ponds, and lakes all the way to the top.

QUICK HIKE | South Bubble/Bubble Rock, Acadia National Park:~1.5 miles. Although the Bubble Mountains are an impressive sight when viewed from Jordan Pond along the Park Loop Road, they’re actually well under 1,000 feet above sea level. It takes less than a mile to reach South Bubble and nearby geological oddity Bubble Rock (via the Bubbles Divide Trail and the Bubbles Trail), which means the going gets quite steep in parts. But the view from the top back to the Atlantic Ocean is exceptional, especially when you add in autumn color.

Fall Massachusetts Hikes

Mount Greylock, Adams: ~6.6 miles. This 3,491-foot mountain has been a favorite of outdoor enthusiasts since the early 19th century, capturing the imagination of Hawthorne, Thoreau, and Melville (who even dedicated his novel Pierre to Greylock’s “Most Excellent Purple Majesty”). Today it’s the centerpiece of some 12,500 acres of state reservation land and an unbeatable challenge for adventurous leaf peepers. The easiest hike to the top, a loop primarily set on the Cheshire Harbor Trail, still requires about four to five hours of moderate to strenuous effort. The payoff: looking out at a landscape that encompasses five states, several mountain ranges, and an ocean of glowing autumn leaves.

Quabbin Reservoir (Gate 40), Petersham:~8 miles. A place of wonder for nature lovers, this sprawling reservoir in central Massachusetts came with a cost: Four villages in the Swift River Valley were flooded to make way for the project in the 1930s. You can still see traces of what came before on this easygoing out-and-back hike, which starts at Gate 40 off Route 32A in Petersham and mixes history and foliage hues as it passes through the remnants of the “lost town” of Dana on the way to the shores of the biggest body of water in Massachusetts.

Skyline Trail, Milton: ~9 miles.As majestic as undiluted nature can be, the Boston skyline rising above a sea of red and gold leaves is a peak experience in its own right. The 7,000-acre-plus Blue Hills Reservation—the largest open space within 35 miles of the city—has long been a favorite place for Bostonians to get a new perspective on their home, thanks to its bountiful hills and lookouts and more than 120 miles of trails. The premier route is the Skyline Trail, which traverses the east-west length of the reservation. It briefly splits at park headquarters into north and south trails; the former is longer and more strenuous but boasts some of the finest views. Note: Requiring an estimated five hours and some tough climbing, the Skyline Trail is best done one-way to start, so grab a buddy and plan a car shuttle.

Wachusett Mountain, Princeton: ~6.2 miles.Dubbed the “Observatory of Massachusetts” by Thoreau, Wachusett Mountain is the loftiest peak within easy 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. One of the loveliest places to start is Mass Audubon’s Wachusett Meadow Sanctuary—a terrific foliage destination in and of itself—where you can pick up the Midstate Trail into the adjacent state reservation for an out-and-back climb via the Harrington Trail straight to the 2,006-foot summit.;

QUICK HIKE | South Sugarloaf, South Deerfield: ~1.4 miles. Not to be confused with its much bigger cousin in Maine, this Sugarloaf Mountain is, for nature lovers, a literal sweet spot. Combining the Pocumtuck Ridge and Old Mountain trails, this loop up and over the south summit is short yet challenging enough to get the endorphins going, and the 652-foot summit, toppedwith 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.

Fall New Hampshire Hikes

Arethusa Falls and Frankenstein Cliff, Hart’s Location:~5 miles. New England’s fall foliage is stunning on its own, but sometimes the landscape offers a little something extra—in this case, a 600-foot-high cliff, a view of a historic railroad line, and the highest waterfall in New Hampshire. Tucked away within Crawford Notch State Park in the White Mountains, this loop hike has some steep climbing through deciduous forest up to Frankenstein Cliff, where a lookout gives views of Crawford Notch and the Saco River below. You’ll also get a sneak preview of what lies ahead: Arethusa Falls, which many consider the state’s most scenic waterfall.

Mount Monadnock, Jaffrey:~4.2 miles.It’s a National Natural Landmark and one of the most-climbed mountains in the world for a reason [see “One Day in October,” p. 98]. Though you can take your pick from any of the fine trails at this 3,165-foot peak, we recommend that first-time hikers head up via the White Dot Trail and descend by way of the White Cross Trail. At the bald summit, you can look out toward Boston, some 65 miles away, and drink in the autumn color of countless acres of protected highlands below.

Percy Peaks, Stratford:~6.7 miles. The most easily recognizable peaks in the Great North Woods beckon to hikers looking to avoid the White Mountains crowds while maxing out on foliage vistas. Head to the remote 40,000-acre Nash Stream Forest for this challenging loop hike summiting South Percy and North Percy, with the latter’s bald granite dome yielding a stunning panorama that takes in Mount Washington and the Presidentials as well as peeks into Vermont, Maine, and Canada. Plus, look for blueberry barrens at the summit to be blazing red in fall.

Welch and Dickey, Thornton:~4.5 miles. You’ll want to start early and/or pick a weekday to avoid crowds on this popular loop trail in the southern Whites, but it’s worth it. Connecting the Welch and Dickey mountains, the route boasts nearly two miles of open ledges that give prime views of the hardwood-carpeted bowl between the two peaks as well as shots of many mountains in the surrounding ranges. Some tricky rock scrambling is required; go counterclockwise in order to climb, rather than descend, the toughest slabs.

QUICK HIKE | West Rattlesnake Mountain, Holderness:~1.8 miles. Many folks looking for an easy climb in the Lakes Region head not to Winnipesaukee but Squam, which is much smaller but just as stunning, and dotted with scenic islands. You can get a bird’s-eye view with a hike up West Rattlesnake Mountain, mainly on the family-friendly Old Bridle Path. The mostly dirt path traverses hardwood forest—meaning ample fall color—before reaching the summit, where granite ledges offer eye-popping views of Squam.

Fall Rhode Island Hikes

Long Pond/Ashville Pond, Hopkinton: ~4.4 miles. Scramble over glacier-dumped boulders and under mountain laurel on this relatively short but challenging day hike along a portion of the 22-mile Narragansett Trail. Starting from the parking area on Canonchet Road, take the Long Pond Trail through Audubon wildlife refuge lands to reach the high bluffs above Ell and Long ponds, a truly breathtaking spot (part of the 2012 movie Moonrise Kingdom was filmed here). Then retrace your steps and dip south on a gentler portion of the Narragansett Trail to the forested shores of Ashville Pond before heading back to your car.

Tillinghast Pond, Coventry:~8.4 miles. Situated on conserved lands in the heart of the largest coastal forest between Boston and D.C., the Tillinghast Pond area is the kind of wooded oasis that makes for a don’t-miss foliage destination. Heading east from the parking areas, this loop hike meanders through woodlands dotted with boulders, old cemeteries, stone walls, and cellar holes on the Flintlock and Wickaboxet trails before rounding back to the signature Tillinghast Pond Trail, which offers a number of overlooks above the beautiful 41-acre pond.;

Walkabout Trail, CHEPACHET:~8 miles. New England hikers can thank Australia for this one: Members of that country’s navy volunteered to build the Walkabout Trail back in 1965 while in Rhode Island waiting for their ship to be readied for its trip back Down Under. Located in the George Washington Management Area, the trail is broken into three loops of varying distances, but the longest circuit—marked with orange blazes—is still moderate enough for most hikers. Quiet woodlands and wetlands predominate, and at the Bowdish Reservoir you can tack on the 1.4-mile Angell Loop to linger by the water.

QUICK HIKE | Norman Bird Sanctuary, Middletown:~2 miles. At this 300-acre-plus nature preserve, hikers are treated to a mix of open fields and foliage-tinted forest, not to mention wildlife aplenty (bring your binoculars, as fall is a busy bird migration season). Try the Hanging Rock Trail, an out-and-back along a ridge that leads to a short cliff with views of Gardiner Pond and the ocean.

Fall Vermont Hikes

Bromley Mountain, Peru:~6 miles. Immerse yourself in a palette of autumn colors on this moderate trek along a portion of the Long Trail/Appalachian Trail to the top of Bromley Mountain. Much of the route is spent in a hardwood forest with brooks, bridges, and boulders along the way, eventually leading out onto a ski slope and the final push to the 3,280-foot summit. Open and grassy, it’s a great place for an autumn picnic, as you take in a sweeping Green Mountain National Forest panorama and fuel up for the hike back.

Camel’s Hump, Huntington:~5.8 miles.Camel’s Hump may not be Vermont’s most-climbed mountain (that would be Mount Mansfield), but its views take a back seat to none. Plus, it offers a true escape from civilization, as this state park is completely undeveloped, with no visitor facilities. This loop hike starts from the park’s Huntington side and follows the Forest City Trail up the southern ridge; connects with the Long Trail to reach the summit; and descends via the Burrows Trail. Bring water and lots of snacks, because this one will make you work—just as surely as the autumn scenery will make you swoon.

Hunger Mountain/White Rock Mountain, Middlesex:~6.4 miles.Located at the southern end of the Worcester Range, Hunger and White Rock are accessible day-hiking destinations that still embody the feeling of remote beauty that befits Vermont’s last undeveloped mountain range. A rugged loop hike on the Middlesex, Waterbury, and White Rock trails provides twice the bang for the buck by connecting these two scenic peaks, both featuring wide-open summits above slopes of mixed hardwood forest. From Hunger’s south summit, you can look west across the valley to take in almost every peak in the Green Mountain Range.

QUICK HIKE | Mount Hor, Sutton:~2.8 miles.Mount Hor rises above the southwestern shores of Lake Willoughby, the loveliest lake in the Northeast Kingdom, not to mention the state. And while its twin across the lake, Mount Pisgah, may have better views, the easier route to Hor’s summit (up the Herbert Hawkes Trail) delivers maximum water-and-color spectacle for minimal effort.