Hiking Massachusetts Peaks

Mass 50 Public Peaks elevation rank: #48
Elevation: 1,622 feet
Prominence: 200 feet
Isolation:  0.76 miles
Summit coordinates: 42°14’53.8″N 73°20’25.7″W
Town: Great Barrington, Massachusetts
Conservation Area: Monument Mountain Reserve (Trustees of Reservations)

Links:
Peeskawso Peak on Peakbagger
Peeskawso Peak on Listsof John
Peeskawso Peak on AllTrails
Monument Mountain Reserve (Trustees of Reservations)

General info: Peeskawso Peak in Great Barrington, Massachusetts, is the most accessible lookout on Monument Mountain, forming its dramatic southern summit. While the mountain’s true high point lies slightly farther north and rises just a bit higher, that northern summit is densely wooded and inaccessible by trail. Peeskawso, by contrast, sits atop rugged quartzite cliffs and a dramatic “knife-edge” ridgeline that delivers sweeping views across the Housatonic River Valley, the surrounding Berkshires, the Taconic Mountains, and—on clear days—even the distant Catskills in New York. One of the mountain’s most striking features is Devil’s Pulpit, a free-standing rock pillar that juts from the cliffs and has captivated visitors for generations.

The 503-acre Monument Mountain Reservation is managed by The Trustees of Reservations and is open year-round from sunrise to sunset. Access is straightforward: a 56-car parking lot is located off Route 7, about 4 miles north of downtown Great Barrington. A $6 parking fee applies to non-members, while Trustees members park for free.

Trail quality throughout the reservation is excellent—well-marked and regularly maintained. Routes to Peeskawso Peak are all under 3 miles but involve a moderate climb of about 650–700 vertical feet, including a bit of rock scrambling near the summit. The hike is short but invigorating, suitable for active families and casual hikers alike. This is one of the most popular hikes in the Berkshires, and on peak weekends the lot often fills by late morning. Of all the peaks on the Massachusetts 50 Highest Public Peaks list, Peeskawso is arguably the most heavily trafficked—perhaps second only to Mount Greylock.

Historical background: Monument Mountain—and Peeskawso Peak—holds deep Indigenous significance. The Mohican people, who have lived in this region since time immemorial, consider the mountain sacred. In pre-colonial times, Mohicans would leave prayer stones in a summit cairn—each one an offering. According to tribal tradition, this cairn marked the grave of a young Mohican woman who leapt from the cliffs for love. Her story was later immortalized by poet William Cullen Bryant in his 1815 poem “Monument Mountain,” which helped give the mountain its name. Though the original cairn was destroyed after the Mohicans were displaced in the 1800s, a reconstructed stone monument now stands along the trail. Today, the Stockbridge-Munsee Community, the modern Mohican tribe, remains actively involved in preserving this heritage.

By the 19th century, Monument Mountain had also become a wellspring of inspiration for European-American writers and artists. Aside from Bryant’s poem, the mountain’s most famous literary connection is an outing in August 1850, when authors Nathaniel Hawthorne and Herman Melville met for a picnic hike here. As legend has it, a sudden thunderstorm drove them into a cave among the boulders, where during their lively discussion Melville found ideas that would later make their way into Moby-Dick. The dramatic landscape and vistas have been celebrated in paintings and writings throughout the 19th and 20th centuries, solidifying the mountain’s reputation as an icon of the Berkshire region’s natural beauty and romantic lore.

In terms of conservation history, Monument Mountain is notable as one of the earliest preserved natural areas in New England. In 1899, philanthropist Rosalie Butler fulfilled her late mother Helen’s wish by donating the mountain’s summit and cliffs to the Trustees of Reservations. In 2021, the peak was officially renamed Peeskawso Peak, meaning “virtuous woman” in Mohican. Two trails were also renamed to reflect Mohican history. These changes mark an important step in honoring Indigenous stories and restoring cultural presence to a landscape still considered sacred today.

Recommended ascent routes: Several scenic trails lead to the top of Peeskawso Peak, allowing for either a direct out-and-back or a more varied loop hike. All routes are well-marked and under 3 miles round-trip.

The Hickey Trail (yellow blazes, 0.83 mi) is the steepest and most direct route to the summit. It climbs steadily through oak–hemlock forest, past a seasonal brook and small waterfall, then switchbacks up ledges to the ridge. With about 600 feet of elevation gain in under a mile, it’s a short but strenuous climb.

The Mohican Monument Trail (blue blazes, 1.5 mi), formerly the Indian Monument Trail, offers a longer, more gradual ascent. This trail winds around the southern flank of the mountain and features interpretive signs, historic stone walls, and remnants of old farm roads and Native footpaths. It’s a good choice for a more relaxed climb or descent.

The Peeskawso Peak Trail (red blazes, 0.6 mi) connects the upper ends of both trails, traversing the narrow, rocky ridgeline to the summit. This stretch offers the best views—north to Mount Greylock, west to the Catskills—and includes a short spur to Devil’s Pulpit, a dramatic free-standing rock pillar below the cliffs. Don’t miss it—it’s just off the Peeskawso Peak Trail and well worth the brief detour. The ridgeline requires some scrambling but remains non-technical.

Many hikers combine all three trails in a 2.5-mile loop—ascending via the Hickey Trail, crossing the summit ridge via the Peeskawso Peak Trail, and descending the Mohican Monument Trail. The route offers a balance of challenge, scenery, and historical interest.

Nearby Mass 50 Highest Public Peaks: Benedict Pond Peak and Mount Wilcox in Beartown State Forest are just a short drive away from Monument Mountain. These could definitely be done in the same day if you’re looking for a longer adventure. And Hunger Mountain is just a little further to the east if you really want to be ambitious.