20 Must-Do Hikes Across Massachusetts, Region By Region
Lacing up your boots in Massachusetts leads to an adventure that feels different in every corner of the state.
In the Berkshires, trails climb through quiet forests and rolling peaks. Out east, sandy paths cut across coastal dunes with the sound of waves nearby.
In between, you’ll find waterfalls, shaded parks, and stretches of history preserved in stone walls and winding routes.
These hikes aren’t just scenic – they connect you to the spirit of the landscape in unexpected ways. Here are 20 must-do trails, organized region by region, to guide your next outdoor journey.
1. Mount Greylock (Adams)
Standing proud as Massachusetts’ highest peak, this magnificent mountain rewards adventurous hikers with panoramic views spanning five states. The historic Appalachian Trail crosses its summit at 3,491 feet.
During fall, the surrounding landscape transforms into a spectacular tapestry of red, orange, and gold. The summit’s 1930s-built War Memorial Tower adds a touch of history to your wilderness adventure.
2. Mount Race via Race Brook Falls Trail (Sheffield)
Hidden away in the southwest corner of Massachusetts lies a hiking gem that combines cascading waterfalls with ridgeline views.
Your efforts are rewarded twice – first with the multi-tiered Race Brook Falls, then with sweeping vistas along the exposed ridge.
Wildlife enthusiasts might spot hawks soaring overhead while traversing this section of the Appalachian Trail. The moderate challenge makes it perfect for experienced hikers looking to escape the crowds.
3. Bash Bish Falls (Mount Washington)
Imagine the sound of water tumbling 80 feet down a series of dramatic rock formations! Massachusetts’ highest single-drop waterfall creates a natural amphitheater that draws visitors year-round.
During summer months, the crystal-clear pool at the base provides a refreshing (though technically prohibited) swimming spot. Winter transforms the falls into a magnificent ice sculpture worth the careful trek.
4. Monument Mountain (Great Barrington)
Literary history meets natural splendor on this beloved Berkshires trail!
Herman Melville and Nathaniel Hawthorne famously hiked here in 1850, where their mountaintop conversation reportedly inspired aspects of Moby-Dick.
The loop trail offers several vantage points with stunning views of the southern Berkshires. Look for Squaw Peak’s distinctive white quartzite cliff face that seems to glow in the afternoon sun.
5. Mount Tom via New England Trail (Holyoke / Hadley)
Volcanic ridges and cliff faces create a dramatic landscape unlike anywhere else in Massachusetts. The basalt columns formed 200 million years ago provide both a geology lesson and a challenging hike.
Hawks and eagles soar on thermal updrafts along the ridge, making this a premier bird-watching destination during migration seasons.
The trail offers spectacular views of the Connecticut River Valley and the Pioneer Valley’s patchwork of farms and forests below.
6. Mount Norwottuck (Holyoke / Hadley)
What looks like a sleeping giant from below offers one of Pioneer Valley’s most rewarding day hikes. The distinctive Horse Caves along the trail were reportedly used as hideouts during the Revolutionary War.
From the summit, you’ll enjoy a 360-degree panorama featuring the UMass Amherst campus, the Connecticut River’s meandering path, and on clear days, Mount Monadnock in New Hampshire.
7. Sanderson Brook Falls Loop (Chester-Blandford State Forest)
Water lovers rejoice! This hidden gem in western Massachusetts features a series of cascades tumbling through a hemlock-lined ravine.
The moderate 4-mile loop combines forest tranquility with the refreshing spray of a 100-foot waterfall.
Few hikers venture to this remote corner of the state, offering a sense of wilderness solitude rare in Massachusetts.
8. Wachusett Mountain (Princeton)
Rising prominently from the surrounding landscape, this monadnock offers a quick summit adventure with outsized rewards.
On exceptionally clear days, the Boston skyline is visible from the top, despite being nearly 60 miles away!
The mountain hosts a fascinating mix of northern and southern forest species, creating a unique ecological transition zone that changes with each elevation gain.
9. Mount Watatic (Ashburnham)
Along the Massachusetts-New Hampshire border stands this perfect “first mountain” for novice hikers. The relatively short trail (about 3 miles round-trip) delivers impressive rewards with minimal suffering.
Berry pickers flock here in late summer when blueberries and raspberries ripen along the upper slopes.
The summit’s open ledges provide a natural picnic spot with views extending to Mount Monadnock and the Boston skyline on clear days.
10. Tully Lake Loop / Tully Trail (Royalston)
Fancy a wilderness adventure without the mountain climbing? This 7.5-mile loop around pristine Tully Lake combines riverside rambling with waterfall views and forest exploration.
Doane’s Falls, with its series of cascades over ancient stone, provides a perfect midway rest point.
Paddlers often combine this hike with a kayak excursion on the lake, creating a multi-sport adventure day in one of Massachusetts’ most beautiful and least-visited corners.
11. Weir Hill Reservation – Cochichewick Loop (Andover)
History and nature intertwine beautifully on this gentle loop overlooking Lake Cochichewick.
Stone walls crisscrossing the trail tell stories of colonial-era farming that shaped this landscape long before it became a reservation.
The mix of habitats – from pine forest to meadow to lakeshore – makes this an excellent bird-watching destination throughout the year, with over 100 species recorded.
12. Gibbs Mountain Loop (Beverly)
Nestled within a suburban landscape, this hidden treasure offers surprisingly rugged terrain and delightful solitude.
Massive granite boulders left by retreating glaciers create natural labyrinths to explore between stretches of pine-needle-cushioned trail.
From several overlooks, hikers can glimpse the Atlantic Ocean in the distance, creating a perfect blend of woodland and coastal hiking experiences in one compact adventure.
13. Rocky Woods Reservation – Ridge and Cedar Hill Loop (Medfield)
Just 30 minutes from Boston lies a peaceful forest escape with surprising diversity. Five pristine ponds dot the landscape, connected by well-maintained trails that wind through oak and pine forests.
History buffs will appreciate the remnants of colonial-era quarries and mill sites along the route.
Cedar Hill rewards modest climbing effort with views of the surrounding countryside, while fishing enthusiasts can try their luck at Echo Pond, stocked with trout in spring.
14. Ward Reservation (North Andover)
Three hills with three distinct personalities await at this diverse conservation area.
The “Solstice Stones” atop Holt Hill mark astronomical alignments and provide a unique destination unlike any other Massachusetts hiking spot.
From the highest point in Essex County, hikers enjoy panoramic views stretching from Boston’s skyline to New Hampshire’s mountains, making this modest elevation gain deliver maximum scenic rewards.
15. Breakheart Reservation (Saugus)
Urban wilderness doesn’t get better than this rugged forest nestled within Boston’s suburbs!
Two freshwater lakes provide swimming opportunities in summer, while rocky outcrops offer surprisingly challenging hiking options.
Fall transforms the reservation into a photographer’s paradise as maple trees create a crimson canopy above the trails.
16. Blue Hills Reservation – Great Blue Hill via Skyline Trail (Milton)
Just minutes from downtown Boston stands a wilderness area that’s been protecting hikers since 1893!
The challenging Skyline Trail offers rocky scrambles and stunning vistas as it traverses the reservation’s most impressive peaks.
The historic Blue Hill Observatory at the summit has been recording weather data continuously since 1885.
17. Middlesex Fells – Skyline Loop (Medford)
Urban adventurers, rejoice! This rocky, root-strewn loop delivers a genuine wilderness experience despite being visible from Boston skyscrapers.
The challenging 7-mile trail traverses ridge lines, circles reservoirs, and passes historic stone structures. Wright’s Tower provides a perfect mid-hike rest spot with panoramic views.
The diverse forest harbors over 100 bird species and surprisingly abundant wildlife, creating a natural oasis that has protected urban sanity since becoming one of America’s first public reservations in 1894.
18. Great Island Trail (Wellfleet, Cape Cod)
Sand between your toes and salt air in your lungs make this Cape Cod hike uniquely refreshing!
Once an island but now connected by sand deposits, this peninsula offers a rare combination of forest, dune, and beach hiking.
Timing is everything here – check tide charts before setting out, as portions of the trail disappear underwater during high tide, adding a delightful element of adventure planning.
19. Cape Cod National Seashore Trails (Eastham / Truro / Provincetown)
Where else can you hike through maritime forests, over sand dunes, and alongside dramatic Atlantic-facing cliffs in one adventure?
The National Seashore’s interconnected trail system offers incredible diversity for coastal explorers. The Atlantic White Cedar Swamp Trail’s boardwalk takes you through an otherworldly ecosystem.
For maximum drama, try the Great Island Trail or Pamet Area Trails, where you’ll experience the raw power of oceanic forces that continuously reshape this dynamic landscape.
20. Menemsha Hills (Martha’s Vineyard)
Island adventures await at this hidden gem on Martha’s Vineyard’s north shore! The trail system combines woodland rambling with spectacular coastal views from the second-highest point on the island.
Brickyard Beach offers a fascinating glimpse into the island’s industrial past with clay cliffs and remnants of a 19th-century brickmaking operation.
Lucky hikers might spot ospreys fishing offshore or harbor seals lounging on distant rocks, adding wildlife excitement to this quintessential New England coastal experience.
