Monument Mountain Hike in Great Barrington, MA: Trails, Parking, Views & Local Tips
- Amber in New England
- Jul 25, 2021
- 6 min read
Updated: Jan 25
Monument Mountain in Great Barrington, MA is a short but surprisingly rugged hike with rewarding summit views. This guide covers the best Monument Mountain trails, parking, maps, and seasonal tips for hiking Monument Mountain safely and efficiently.
Steep climbs, rocky summits, and the iconic Devil’s Pulpit make it a full morning adventure, followed by local eats and optional sunset views at Bartholomew’s Cobble.
Monument Mountain Reservation is protected land managed by The Trustees of Reservations and has long inspired writers and thinkers, including Herman Melville and Nathaniel Hawthorne, who reportedly visited the mountain during their time in the Berkshires. Today, it remains one, if not the most scenic and rewarding Great Barrington hikes, combining history, geology, and beautiful summit views.
(Quick Disclosure: This guide contains affiliate links. I may earn a small commission if you buy through them, at no extra cost to you. I only recommend gear I trust on the trail.)
Monument Mountain Hike Guide: Trails, Maps & Parking (Great Barrington, MA)
Monument Mountain is one of New England’s most scenic hikes, located in the Berkshires of Massachusetts.
Monument Mountain’s trail names, including Mohican Monument Trail and Peeskawso Peak, reflect the area’s Indigenous history and cultural heritage.
Along the way, you’ll encounter Devil’s Pulpit, a narrow rock outcrop with dramatic drop-offs. The views are incredible, but this section requires caution, especially when trails are wet, icy, or snowy.
This guide covers:
Trail logistics: parking, timing, and difficulty
Gear tips: what to wear and pack for New England conditions
Food stops: pre- and post-hike spots in Great Barrington
Optional scenic add-ons: like Bartholomew’s Cobble for sunset views
By the end, you’ll have a practical, full-day itinerary for a safe and scenic adventure in the Berkshires.
Monument Mountain Loop Hike: Quick Tips & Key Info
Loop: Mohican → Peeskawso → Hickey (~2.5–3 miles)
Difficulty: Moderate–Strenuous
Duration: 2–3 hours
Parking: Monument Mountain kiosk (check rates)
Gear: Trekking poles, sturdy boots, layers
Best Time: Early morning or weekdays
Caution: Slippery rocks, exposed ledges at Devil’s Pulpit
Monument Mountain Hike: Mohican Trail → Peeskawso Peak → Hickey Trail
The Monument Mountain loop offers a mix of moderate climbs, rocky scrambles, and rewarding summit views. Here’s a breakdown to plan your hike safely and efficiently:
Monument Mountain Trails: Distance, Difficulty & Timing
Total Distance: ~2.5 miles for the main loop (extendable with Willow’s or Cross Over Trail)
Summit: Peeskawso Peak, 1,642 feet
Estimated Time: 2–3 hours, longer if you stop for photos or breaks
Difficulty: Moderate to strenuous, depending on trail choice and weather
(Looking for other easy-to-moderate Connecticut trails? See our CT Hikes guide.)
Recommended Loop
I usually hike Monument Mountain as a loop: Mohican Trail → Peeskawso Peak → Hickey Trail. This route is roughly 2.5 miles total and takes 2 hours, depending on breaks for photos, snacks, or water.
Gradual ascent along a former carriage road
Mostly under 15% grade. Good for beginners or a gentle start
Scenic forest views and small streams
Summit: Peeskawso Peak Trail (Red)
Short but requires rock scrambling over jagged quartzite boulders
Watch footing; wet or icy conditions increase risk
Return: Hickey Trail (Yellow)
Steep, 0.8-mile descent with stone steps and exposed roots
Trekking poles recommended for stability and knee protection
⚠️ Caution: Slippery when wet or snowy; caution especially around Devil’s Pulpit
Key Features & Hazards
Devil’s Pulpit: Narrow ledge with steep drop-offs. Stunning views, but exercise caution year-round. It's slippery in rain, snow, or ice.
Waterfall: Small, seasonal waterfall along Hickey Trail; can be icy in winter.
Views: Summit and Devil’s Pulpit provide wide vistas. On clear days, you may see Vermont.
Monument Mountain Gear & Safety Tips
Wear sturdy, trail-ready footwear. Check out my guide to the 10 best women's hiking boots for tackling New England's slick, rocky trails.
Layer appropriately: moisture-wicking base, fleece or jacket for exposed peaks.
Bring water, snacks, and a small first aid kit.
Hike early in the day or weekdays for quieter trails and easier parking. Summer weekends can get busy.
Keep pets leashed and children close near cliff edges.
Monument Mountain Parking & Trailhead Info
Parking for Monument Mountain is managed by The Trustees of Reservations at the Monument Mountain Reservation parking lot off Route 7 in Great Barrington, MA.
Parking Details:
Location: Monument Mountain Reservation lot, Route 7, Great Barrington
Cost: ~$6 per vehicle for non-members (free for Trustees members)
Payment: Kiosk at the parking lot
Capacity: Small lot — fills quickly on summer weekends and foliage season
💡 Pro tip: Arrive before 9am on weekends, especially in fall. If the parking lot is full, you may need to wait for a space as roadside parking is not allowed.
Monument Mountain Pre-Hike Fuel & Breakfast Spots
Start your day with energy that won’t weigh you down. Early morning or weekdays are quieter, so you can grab a seat and avoid crowds.
Fuel on Main Street (293 Main Street): Coffee, snacks, and often live music.
Bear Butter (323 Main Street): Try the Healthy Elvis smoothie—portable if you want a trail snack.
Cafe Holli (200 Main Street): Quiet spot with pastries and coffee.
Great Barrington Bagel Company (777 S Main Street #1): Quick, hearty breakfast; the tornado bagel is filling.
Pro Tip: Bring a small snack and water for the hike, especially if you plan to tackle the Hickey Trail.
Monument Mountain Post-Hike Lunch & Local Eats
After the hike, you’ll want something filling and local. Options near the parking area:
Barrington Brewery & Restaurant (420 Stockbridge Road): Fresh pretzels and house-brewed beers.
The Well (312 Main Street): Popular for nachos and casual lunch.
Siam Square Thai Cuisine (290 Main Street): Veggie spring rolls and green curry.
Fiesta Bar & Grill (284 Main Street): Hibiscus margarita and hearty plates.
SoCo Creamery (5 Railroad Street): Ice cream for a sweet finish.
Los Lopez Taco Truck (198 Main Street): Quick snack or late lunch option.
Agaves Mexican Grill (389 Stockbridge Road): Fresh ingredients and large portions.
Tip: Check opening hours if visiting off-season.
Monument Mountain sits just over the border from northwest Connecticut, making it an easy add-on for hikers exploring the region. If you’re building a full weekend around short, scenic hikes, Northwest Connecticut has some of the best bang-for-your-buck trails in New England.
For a broader trip, Litchfield County offers a mix of easy hikes, scenic drives, and small towns that pair perfectly with a Berkshires day trip.
Monument Mountain Nearby Hikes: Bartholomew’s Cobble Detour
On your way back to Connecticut, consider a short detour for sunset views at Bartholomew’s Cobble in Sheffield for sunset views over the Housatonic River Valley:
Trail Highlight: Tractor Path (~1.3 miles) to Hurlburt’s Hill
Fee: $5 if not a member
Timing: Late afternoon for best light
Monument Mountain Seasonal Hiking Tips & Packing Guide
Start your day: Grab coffee or a light breakfast at Rio Cafe, Fuel, or Bear Butter.
Hike: Loop via Mohican → Peeskawso Peak → Hickey Trail (~3 miles, 2–3 hours). Be aware of steep sections, rock scrambles, and Devil’s Pulpit. Trekking poles recommended on Hickey Trail.
Safety Notes: Trails can be slippery in snow, rain, or early spring melt. Keep pets leashed and children close near ledges. Early mornings or weekdays are quieter.
Post-hike refuel: Lunch or snacks at Barrington Brewery, The Well, Fiesta Bar & Grill, or SoCo Creamery.
Optional stop: Bartholomew’s Cobble for a short trail (~1.3 miles) and sunset views.
❄️ Monument Mountain Seasonal & Packing Tips
Winter Hiking Tips
Trails can be icy or snowy, especially Devil’s Pulpit. Extreme caution required.
Wear traction devices (microspikes or Yaktrax) on boots.
Layering is key: base layer + fleece + waterproof outer layer.
Pack snacks and water, even for a short loop, and bring a phone for safety.
Early morning or weekdays = least crowded parking.
Spring Hiking Tips
Trails may be muddy; waterproof boots recommended.
Watch for slippery rocks near waterfalls or outcrops.
Spring flowers can make trails beautiful, but stay on path to protect plants.
Summer Hiking Tips
Trail is generally dry; rock scrambling easier.
Bring plenty of water, shaded areas are limited.
Start early to avoid midday heat and secure parking.
Fall Hiking Tips
Foliage is stunning, but trails can be crowded on weekends.
Rocks may be slick with fallen leaves.
Layer lightly; mornings can be chilly, afternoons warm.
Gear Tip: I always carry a lightweight, moisture-wicking base layer (Base Layer Guide) and a trail-tested fleece (Fleece Guide) for warmth and sweat management on exposed peaks.
Frequently Asked Questions About Hiking Monument Mountain in Great Barrington, MA
Q1: What is the best time to hike Monument Mountain?
A: Fall foliage (Sept–Oct) and spring wildflowers (Apr–May) are ideal. Winter requires traction gear and caution on icy ledges.
Q2: How difficult is Monument Mountain?
A: Moderate–strenuous. The loop involves steep climbs, rocky scrambles, and exposed ledges at Devil’s Pulpit.
Q3: Can I bring my dog or kids?
A: Yes, dogs are allowed on leash and children can hike with supervision. Extra caution is required near Devil’s Pulpit.
Q4: Where can I park for Monument Mountain?
A: Parking is at the Monument Mountain Reservation lot off Route 7 in Great Barrington (~$6 non-members). Arrive early in peak season to secure a spot.
👉 More Short Hikes Near Monument Mountain
Northwest Connecticut short hikes - Easy to moderate trails just south of the border, perfect for half-day adventures or trip extensions.
Litchfield County spring itinerary – A relaxed itinerary combining hikes, food stops, and scenic drives close to Great Barrington.
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