Hiking Monument Mountain: 3 Trails, Best Views & Local Guide
- Amber in New England
- Jul 25, 2021
- 5 min read
Updated: 9 hours ago
Monument Mountain is a short but surprisingly rugged hike near Great Barrington, MA with rewarding views. 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. Here’s everything you need to plan your day.
(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 is one of New England’s most scenic hikes, located in the Berkshires of Massachusetts.
Monument Mountain’s Mohican Monument Trail and Peeskawso Peak names reflect the area’s Indigenous history and meaningful cultural heritage.
Along the way, you’ll encounter Devil’s Pulpit, a narrow rock outcrop with dramatic drop-offs. Worth the view but take caution, especially when trails are wet or snowy. The hike itself is just under 3 miles for the main loop, though you can extend with side trails.
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 Quick Tips
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 Trail Logistics & 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.
Gear & Safety Tips for Monument Mountain Hike
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.
Monument Mountain now requires paid parking, which may help limit crowds. Check the Trustees of Reservations site for up-to-date kiosk rates.
$6 parking fee for non‑members (members park free).
Keep pets leashed and children close near cliff edges.
Pre-Hike Fuel: Coffee & Light Breakfast
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.
Post-Hike Refuel: 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.
Optional Scenic Stop: Bartholomew’s Cobble
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 Day Trip: Quick Summary
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
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
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
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
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.
👉 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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