TOP 25 HIKES IN MASSACHUSETTS



I am proud to present what I believe to be the top 25 hikes in Massachusetts! This list is based upon a mix of personal experience of hiking throughout the state for the past fifteen years and a thorough review of dozens of websites and just about every hiking guidebook that has been published on hiking in Massachusets over the past two decades.

Each of these hikes is exceptionally memorable - you can't go wrong with any of them. This list is in random order - it is not sorted by rank.

If you would like detailed driving directions and trail guides for these hikes, I recommend purchasing these long-trusted hiking guidebooks:




BARTHOLOMEW'S COBBLE RESERVATION / HULBURT'S HILL
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 1.3 miles one-way to Hulburt's Hill; there are a total of 5.0 total miles of trails in the reservation Easy / Moderate this highly enjoyable hike climbs moderately along the Tractor Path for 1.3 miles to beautiful northward-facing views from the field atop Hulburt's Hill; for a trail map of this lovely Trustees of Reservation property, click here; the trailhead and visitor center for the reservation is on Weatogue Road in Ashley Falls

Hulburt's Hill, Bartholomew's Cobble DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MOUNT WATATIC
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 3.0 mile loop Moderate / Difficult Mount Watatic offers some of the finest views in central Massachusetts; portions of the Wapack Trail are fairly steep, so you may want to avoid this trail when it's wet or icy; the trailhead is on MA 119 (Rindge State Road) in Ashburnham; here's a trail map that shows you the loop, which you can hike either clockwise or counterclockwise (I recommend counterclockwise since the southern portion of the Wapack Trail is much steeper than the northern portion or the State Line Trail)

view from Mt. Watatic DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

BASH BISH FALLS
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 0.8 miles
round-trip
Easy / Moderate often described as 'the state's most dramatic waterfall,' Bash Bish Falls is a segmented 80-foot drop of Bash Bish Brook; these falls are perhaps the most well-known and frequently photographed waterfall in Massachusetts; A mighty boulder splits the falls into two sections. Immediately after, the walls surrounding both sides of the falls ricochet the water back together just before crashing into a pool below; there are two trailheads for the falls - one in MA and one in NY

Bash Bish Falls DIRECTIONS / TRAIL INFO
New England Waterfalls

LYNN WOODS RESERVATION
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA Varies based on trails used Easy / Moderate Lynn Woods offers one of the premier hiking and mountain biking destinations in eastern Massachusetts; when open, a historic stone tower offers great views of the Boston skyline (in the past, it has only been open on select Saturdays in summer); bring a flashlight in case you find 'Dungeon Rock' (a cave that is sometimes open on Saturdays in summer); don't let the fact that this park is located in the city of Lynn turn you off...it is a fantastic place and urban areas all over the country should be jealous of it

Lynn Woods Reservation DIRECTIONS / TRAIL INFO
Lynn Woods Reservation Trail Map

ATLANTIC WHITE CEDAR SWAMP TRAIL
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 1.2 mile loop Easy / Moderate this is one of Cape Cod's finest easy day hikes; walk a boardwalk trail though an interesting white cedar swamp; the trailhead is at the Marconi Station Area of South Wellfleet (Marconi Station Road); some portions of the trail are a bit sandy

Atlantic White Cedar Swamp Trail DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MOUNT GREYLOCK / MOUNT GREYLOCK STATE RESERVATION
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA Varies based on trails used Difficult there are dozens of miles of trails on Mount Greylock, which is the highpoint of Massachusetts; the Appalachian Trail also crosses the park; to understand all of your hiking and backpacking options in this large reservation, consult the trail map of the Mount Greylock State Reservation here; there are many waterfalls on the slopes of Mt. Greylock that can be explored as well, including March Cataract Falls, Deer Hill Falls, Falls on the Bellows Pipe Trail, Pecks Falls, and Money Brook Falls; take note that you can also drive to the summit of Mt. Greylock, but it's more fun to hike it and also enjoy the views on the way up

summit of Mt. Greylock DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

DOGTOWN / BABSON BOULDERS
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA Varies based on trails used Easy / Moderate Dogtown offers arguably the best hiking on Cape Ann; don't miss the Whale's Jaw or the famous Babson Boulders (more than 30 boulders with words of advice and inspiration carved deep into them); this conservation park is extremely large, so find and bring a good trail map; here is a good map that shows the approximate location of most of the Babson Boulders

Babson Boulders, Dogtown DIRECTIONS / TRAIL INFO
Babson Boulders Trail Map

MOUNT RACE / MOUNT EVERETT / RACE BROOK FALLS
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 7.0 miles
round-trip
Difficult the 7.0 mile hike I have suggested here includes the hike up scenic Mt. Race and Mt. Everett; at least five noteworthy waterfalls and two summits with great views are experienced on this trail; backcountry tentsites are available at Race Brook and Laurel Ridge tentsites; the trailhead for this hike is on MA 41 just north of the Connecticut/Massachusetts border; you can also do this hike as a traverse by using two vehicles and starting at the East Street / Mount Washington Road trailhead in Connecticut just south of the MA/CT border (hike east to the Appalachian Trail and then hike north)

Race Brook Falls DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide
New England Waterfalls

APPALACHIAN TRAIL ('AT')
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA up to 90.2-miles
one-way
(shorter day hike options are possible)
Moderate to Difficult
(depending upon which section(s) are hiked)
90.2 miles of the 2,190 mile-long Appalachian Trail reside in Massachusetts; the elevation of the AT in Massachusetts ranges from 650ft to 3,491ft; there are many overnight shelters and tentsites along the way; the best sections of the AT in Massachusetts are in the southern and northern portions of the state (the central section is less crowded but also less interesting); the very best highlights of the AT in Massachusetts include Mt. Race and Mt. Greylock

Mt. Race DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

PINE COBBLE & EAST MOUNTAIN
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 3.2 miles round-trip Moderate this is an enjoyable hike to good views of the Hoosic River Valley; the trailhead for this hike is on Pine Cobble Road in Williamstown

view from Pine Cobble DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

BAY CIRCUIT TRAIL ('BCT')
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA up to 230-miles
one-way
(shorter day hike options are possible)
Easy / Moderate
(the difficulty depending upon which section(s) of the trail is hiked)
the BCT is a fantastic and varied 230-mile trail that loops around Boston; most will use two vehicles and hike it in 5-12 mile segments; this trail is impossible not to enjoy since it passes through dozens of conservation areas, farms, historical areas, and many other interesting natural and man-made environments; a detailed map and a turn-by-turn trail instructions (which can be found on the website of the BCT) is recommended as not all areas are posted well with trail markers

bridge on the Bay Circuit Trail DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide
Bay Circuit Trail Map & Guide

PURGATORY CHASM STATE RESERVATION
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 0.5 miles
round-trip
Moderate come here and explore the fun rock formations of one of Massachusetts' finest state parks; if you like boulder caves and/or rock scrambling, you will find no better place in southern New England; rock walls tower to 70 feet and are popular with skilled rock climbers; the park also has picnic tables and a nice playground for kids; there are some officially marked hiking trails within the park, but it's more fun to just clamber up and down all the rocks; this is not a safe place for very young kids (I wouldn't bring a kid here that's under 4 unless you have them on a kids' leash); don't miss trying to squeeze through the Fat Man's Misery (shown in the picture below)

Fat Man's Misery, Purgatory Chasm DIRECTIONS / TRAIL INFO
Purgatory Chasm Trail Map

WARD RESERVATION
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA there are 10 miles of trails in the reservation Easy / Moderate highlights of this reservation include interesting granite stones and good views of Boston from atop Holt Hill; another trail that stems from the parking lot on Prospect Road visits a bog; this reservation is located in Andover and is one of the best of the Trustees of Reservations' 110+ managed properties in Massachusets

Holt Hill, Ward Reservation DIRECTIONS / TRAIL INFO
Ward Reservation

ALANDER MOUNTAIN
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA Varies based on trails used Moderate / Difficult there are several routes to climb this mountain, which provides some of the best views in southwestern Massachusetts; you can hike from Bash Bish Falls State Park, from East Street, or from the Robert Brook Trail from New York; here's a trail map to see all your trail options; there is a cabin (free; first come, first served) that you can stay in overnight near the summit, but it's in rough shape and could use some rehabilitation

No Photos On File DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

ROBERT FROST TRAIL
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA up to 47-miles
one-way
(shorter day hike options are possible)
Moderate to Difficult this beloved footpath runs from South Hadley to Wendell State Forest, passing several scenic attractions, including Mount Toby and the Holyoke Range; the trail passes through the following towns: Hadley, South Hadley, Amherst, Granby, Belchertown, Pelham, Shutesbury, Leverett, Sunderland, Wendell and Montague

No Photos On File DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

BLUE HILLS RESERVATION
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA there are more than 125 miles of trails in the reservation Easy / Moderate it's truly amazing that a reservation so close to Boston has withstood development and has more than 125 miles of trails; this reservation offers a variety of interesting trails, some of which offer views of the Boston skyline; the Appalachian Mountain Club rents cabin rentals and campsites near Ponkapag Camp within the park (information on those facilities can be found here)

No Photos On File DIRECTIONS / TRAIL INFO
Blue Hills Reservation

GREAT ISLAND TRAIL
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA up to 3.5 miles
one-way
Easy / Moderate this is perhaps Cape Cod's wildest trail; you'll walk miles of deserted beach, which means you may see all sorts of treasures of the sea that get deposited onto the beach (be aware that you may also see some dead animals from time to time too)

Great Island Trail, Cape Cod DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

METACOMET-MONADNOCK TRAIL ('M&M')
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA up to 114-miles
one-way
(shorter day hike options are possible)
Easy to Moderate
(depending upon which section(s) of the trail is hiked)
this rural and scenic trail travels in a north/south direction from the town of Southwick in central Massachusetts to the summit of Mt. Monadnock in New Hampshire; if you are looking for an even longer backpacking trip, this trail also connects with the Metacomet Trail in Connecticut and the Monadnock-Sunapee Greenway Trail in New Hampshire; highlights of the Metacomet-Monadnock Trail include the summits of Mount Tom, Mount Holyoke, and Mount Monadnock, along with the firetower atop Mt. Grace, several waterfalls and other natural and historical features

Mount Monadnock at the end of the Metacomet-Monadnock Trail DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MIDDLESEX FELLS RESERVATION
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA there are more than 100 miles of trails in the reservation Easy / Moderate there are many nice trails in this large reservation, including the Rock Circuit Trail and the Skyline Trail; the Rock Circuit Trail provides the finest views; there are over 100 miles of trails in this huge reservation, and so you can easily put together a 10+ mile hike if you want to (the Skyline Trail along is about 7.5 miles); if you have a friendly dog, you must visit the Sheepfold at some point (it's a 10-acre open field that often has dozens or even hundreds of dogs playing)

No Photos On File DIRECTIONS / TRAIL INFO
Middlesex Fells Reservation

MIDSTATE TRAIL
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA up to 95-miles
one-way
(shorter day hike options are possible)
Easy to Moderate
(depending upon which section(s) of the trail is hiked)
this long-distance hiking trail in central Massachusetts travels in a north/south directions for 95 miles from the town of Douglas to the town of Ashburnham; highlights of this trail include five overnight shelters and beautiful views atop Mt. Watatic and Mt. Wachusett; there are many day hiking opportunities if you don't want to take the full journey; excellent information and suggested day hikes along the trail can be found at the Midstate Trail's official website here

views from Mt. Watatic along the Midstate Trail DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MONUMENT MOUNTAIN
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 2.3 mile loop
(slightly longer options are also available)
Moderate this is one of the best day hikes in the Berkshires; the ledges on this mountain provide good scenic views; there's a seasonal waterfall here if you visit after heavy rains; the trailhead for the Monument Mountain Reservation is on MA 7 (Stockbridge Road) in Great Barrington; there are several ways you can hike this mountain, so take a look at the trail map here to see your options

No Photos On File DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MOUNT TOM
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 1.0 miles one-way Moderate hike along the Beau Bridge Trail & M&M Trail within the Mount Tom State Reservation up to an lookout tower that provides good views of the Connecticut Valley; there are 22 miles of trails in the reservation if you are looking to get more miles of hiking in; Mount Tom is a popular place for watching hawks in the fall

No Photos On File DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MOUNT WACHUSETT
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA Varies based on trails used Moderate there are many hiking routes within the Mount Wachusett State Reservation; to understand your trail options, refer to the trail map here; several trails offer scenic views; Mount Wachusett is one of the major highlights of the Midstate Trail

No Photos On File DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

TULLY TRAIL
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA 22-mile loop
(shorter day hike options are possible)
Easy to Moderate
(depending upon which section(s) of the trail is hiked)
this fun and varied trail can be section hiked or done as a 1-night backpacking trip using the Royalston Falls Shelter (free; first-come, first-served) or the walk-in campsites at Tully Lake Campground; highlights of the Tully Trail include three waterfalls (Doane's Falls, Spirit Falls, Royalston Falls) plus scenic views on Tully Mountain; extremely strong hikers will often try to do the entire loop in one day; be aware that portions of the trail near Tully Lake may be flooded in early spring or after heavy rainstorms; a trail map can be found here

Royalston Falls, Tully Trail, Massachusetts DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

MOUNT HOLYOKE / MOUNT HOLYOKE RANGE
STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
MA Varies depending upon route chosen Moderate hike to and along open ledges providing excellent views along the Holyoke Range; Mt. Holyoke offers great views of the Connecticut River Valley; there are several adjacent state parks and conservation properties in this area, and so many hiking options are possible; take note that you can drive to the summit of Mt. Holyoke in the summer; one great option is to hike the Metacomet-Monadnock Trail along the entire Holyoke Range

No Photos On File DIRECTIONS / TRAIL INFO
AMC's Massachusetts Trail Guide

RUNNER-UPS

Each of the following trails or hiking areas was a close contender for the 'top 25 hikes' list above. Each of these runner-ups is absolutely worth hiking.


THE HIKE STATE TOTAL MILEAGE DIFFICULTY NOTES & HIGHLIGHTS
Fort Hill Overlook MA 0.75 miles
one-way
Easy offers some of the best views on Cape Cod; trailhead is on Fort Hill Road ( take US 6 to Governor Prence Road to Fort Hill Road); great views of Nauset Marsh; part of the Cape Cod National Seashore; there are more trails in the area, including the Red Maple Swamp Trail
Freedom Trail, The MA 2.5 miles one-way Easy although some would argue this is a 'walk' and not a 'hike', this is an extremely enjoyable cultural and historical walk through the city of Boston; you follow a marked path from Boston Common to the Bunker Hill Monument in Charlestown (or vice versa); there are so many fascinating attractions along this walk, that this is likely considered a top Massachusetts hike by many; the hike also passes by some fantastic playgrounds, tourist attractions and restaurants en route
Harold Parker State Forest MA there are 25 miles of trails in the state forest Easy this large state forest offers mix of paved and unpaved trails and is popular with hikers and mountain bikers; trails pass by several peaceful ponds and marshes; the state park also offers a nice car campground; the Bay Circuit Trail passes through a portion of the forest
Ipswich River Wildlife Sanctuary MA there are 12 miles of trails in the sanctuary Easy this sanctuary has trails that pass wetlands and marshes; don't miss the grotto-like landscape found along the Rockery Trail; this is an excellent birding spot (I've seen owls up close here)
Minute Man National Historical Park MA up to 3.75 miles one-way Easy hike, bike or jog a well-maintained path that passes many historically significant buildings from the Revolutionary War period; the path passes through farms, crosses over meadows on boardwalks, and crosses attractive woodlands; there is a top notch National Park Service visitor center near the eastern end of the trail; the most photogenic spot on the trip is perhaps the Hartwell Tavern; the path is so well-maintained that a baby stroller or jogger would probably be fine
Moose Hill MA 0.5 mile one-way Easy / Moderate short climb to good views within the Moose Hill Audubon Sanctuary in Sharon
Mountain Meadow Preserve MA there are 4.0 miles of trails in the reservation Moderate offers scenic views and passes by several peaceful meadows
Parker River National Wildlife Refuge MA there are a total of 3.0 miles of trails in the refuge Easy one of the premier birding sites in the Northeast; several short hikes plus opportunity to walk for miles on uncrowded beach (when its open); don't miss the boardwalk and firetower lookouts; snowy owls in winter
Royalston Falls MA 0.8 miles
round-trip
Easy / Moderate wild and scenic waterfall along the Tully Trail in the town of Royalston; also drive to and hike to nearby Doane's Falls and Spirit Falls while in the area; there is a first-come, first-served overnight shelter available for backpackers 0.3 mile above Royalston Falls
Pleasant Valley Wildlife Sanctuary MA there are 7 miles of trails in the sanctuary Moderate / Difficult this sanctuary is one of the premier Masssachusetts Audubon conservation properties; there are 7 miles of trail in the sanctuary, including two trails that climb to a firetower; a seasonal but pretty moss-covered waterfall can also be found on the Overbrook Trail (marked as "Hemlock Ravine" on this trail map)
Pocumtuck Ridge Trail MA up to 15.0 miles one-way Moderate / Difficult there are many viewpoints along this 15-mile ridgeline trail; one end of hte trail is at South Sugarloaf Mountain in South Deerfield, MA and the other is at Rocky Mountain in Deerfield, MA; the trail is supposedly well-blazed in most sections, but a GPS may be helpful in others; good information can be found here
Sandy Neck MA up to 12 miles round-trip Easy / Moderate Sandy Neck is a 6-mile long barrier beach that offers trails and beach walking; if you want to do a loop, you can use the #2 or #4 connector trails to do so; see trail map here
Sugarloaf Mountain / South Sugarloaf Mountain MA 1.1 miles one-way Moderate hike up to impressive views of the Connecticut River within the Mount Sugarloaf Reservation; take note that you can also drive to the summit of Mount Sugarloaf
Totem Trail / Mohawk Trail State Forest MA 1.1 miles one-way Moderate / Difficult you'll climb 800 feet in elevation on your way to a scenic rock ledge on this hike; there are more good trails within the state forest if you have additional time and energy; trailhead is on MA 2
Tyringham Cobble / Cobble Hill MA 2.0 mile loop Moderate good views for a small amount of effort in the Berkshires
World's End Reservation MA there are 4.5 miles of trails in the reservation Easy hike the trails and carriage paths of this oceanfront peninsula in Hingham; good views of the Boston skyline; one of the finest coastal hiking areas in southern New England; be aware that parking is limited, and it often completely fills up on weekends

OTHER LISTS BY NEWENGLANDWATERFALLS.COM

Here are some more lists to help you enjoy the awesome hiking trails of New England:
  • Top 25 Hikes in the White Mountains of New Hampshire & Maine = link
  • Top 25 Hikes in New Hampshire = link
  • Top 25 Hikes in New England = link
  • Top 25 Easy Day Hikes in New England = link
  • Top 25 Loop Hikes in New England = link
  • Top 25 Family-Friendly Hikes in New England = link
  • Top Rock Scrambles in New England = link
  • Hiking New Hampshire's 4000-Footers = link
  • Hiking New Hampshire's 52 Peaks With A View List = link
  • Hiking the North Shore of Massachusetts / North of Boston = link

HIKING COMMUNITIES ON FACEBOOK



If you enjoy hiking or backpacking in Massachusetts, I recommend that you strongly consider joining some or all of these groups on Facebook. Once accepted into the groups, please share your photos and adventures of hiking and backpacking throughout Massachusetts:
GUIDEBOOKS TO GET YOU THERE

The following guidebooks are trusted resources to help lead you to nearly all of Massachusetts best hikes. Click on any book to read reviews and/or purchase on Amazon.com. I own (and love) each of these guidebooks.






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