Monument Mountain Hike: Trails, Views, & Great Barrington Day Trip Guide
- Amber in New England
- Jul 25, 2021
- 6 min read
Updated: 8 hours ago
Updated: October 2025 | By Amber in New England
The Perfect Berkshire Day Trip
I live in northwest Connecticut, so a day trip to Great Barrington, Massachusetts is about a forty-five minute drive. I usually take Route 7 because it winds through the woods and small “mountains” of CT. It’s one of my favorite scenic drives. Cross the state line into Sheffield, and you’ll find charming antique shops and boutique stops along the way. Keep following Route 7, and you’ll soon arrive in Great Barrington, a small town full of personality and culinary gems.
(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.)
This guide is your complete itinerary for a day trip: we’ll hike Monument Mountain, explore local dining, and even sneak in a sunset view at Bartholomew’s Cobble. Plus, I’ve included tips for trail logistics, parking, and the gear that makes it all more enjoyable.
Fuel Up Before the Hike: Coffee & Smoothies
Before tackling Monument Mountain, you need energy, but not a heavy meal. Here are my top stops near the parking lot:
Rio Cafe (403 Stockbridge Road): Perfect for a light breakfast. I love a fresh fruit smoothie or the vegetarian chili omelet. Outdoor seating beside the river makes it peaceful, even on a busy weekend.
Fuel on Main Street (293 Main Street): Excellent coffee, local goods, and often live music.
Bear Butter (323 Main Street): Don’t miss the Healthy Elvis smoothie.
Cafe Holli: Cozy spot with great pastries and coffee. Perfect if you want a quieter start before heading up Monument Mountain.
Great Barrington Bagel Company (777 S Main Street #1): The tornado bagel with olive pimento cream cheese is my go-to for a quick, hearty start.
Pro Tip: Grab something portable if you plan to snack on the trail. Hydration is key, especially on rocky sections of Monument Mountain.
Monument Mountain Hike: Devil’s Pulpit & Peeskawso Peak
Monument Mountain may not be the longest hike, but it packs steep climbs, jagged rocks, and a few slippery sections. This is not necessarily a beginner hike, especially in winter or early spring. Here’s a breakdown for your day:
Trail Overview
Total Trails: ~6 miles combined, depending on your route.
Main Trails: Mohican Monument Trail, Hickey Trail, Peeskawso Peak Trail. Optional: Willow’s Trail (1.8 miles) or Cross Over Trail (.7 miles).
Summit: Peeskawso Peak, 1,642 feet.
What Makes This Hike Moderate-Strenuous?
While Monument Mountain's loop is relatively short (about 3 miles total), its difficulty is often underestimated. The strenuous rating comes down to two key factors:
1. The Trail Choice: Hickey vs. Mohican
The Strenuous Path: Hickey Trail (Yellow)
This is the shortest route to the summit connector (approx. 0.8 miles).
It features a steep, relentless climb with sustained grades of $15-25\%$, often requiring hikers to step up high stone stairs or navigate large roots and rocky sections.
The Gear Tip: If you choose the Hickey Trail, especially for the descent, trekking poles are highly recommended for stability and to protect your knees from the steep grades. I use Lightweight, Collapsible Trekking Poles on Amazon which make a huge difference. Proper footwear is just as critical: for a hike like this, check out our guide to the 10 best women's hiking boots for tackling New England's slick, rocky trails.
The Easier Path: Mohican Monument Trail (Blue)
This path is longer (approx. 1.5 miles) but offers a much more gradual, leisurely ascent along a former carriage road, keeping grades mostly under $15\%$. It is the recommended choice for beginners or those with mobility concerns.
2. Summit Scrambling and Exposure
Peeskawso Peak Trail (Red): The short trail that connects the main loops across the ridge requires moderate rock scrambling over large, jagged quartzite boulders.
Devil's Pulpit: The path to and around the Devil's Pulpit outcrop is narrow and runs along sheer cliffs and ledges with steep drop-offs. This section requires careful foot placement, especially when wet, icy, or when hiking with children or dogs. This is the main reason why the hike is not considered "easy."
Tip: Bring your camera or phone mount—this is a view you’ll want to capture.
Quick Tips for Scannability
Parking & Fees: Monument Mountain has a kiosk for parking. Check the Trustees of Reservations website for seasonal rates and peak season tips.
Trail Difficulty: Moderate to strenuous. Mohican Trail is “easiest” to reach Inscription Rock (1.6 miles). Hickey Trail is steep and slippery in winter, spikes recommended.
Safety: Keep children close, pets on leashes, and watch for ravines. The Devil’s Pulpit is a hidden but stunning rock formation. Watch your step!
Trail Features: Small waterfall on Hickey Trail; summit views may include Vermont on a clear day.
Gear Tip: Proper footwear is non-negotiable, especially for the jagged rocks on Hickey Trail. 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.
Post-Hike Relaxation: Breweries & Dinner Spots
After hiking, you’ll want something filling and local. Here’s where I go:
Barrington Brewery & Restaurant (420 Stockbridge Road): Raspberry Ale is my favorite, and the fresh pretzels are a must. Their house-brewed beers are excellent.
The Well (312 Main Street): The nachos here are some of the best I’ve had in town.
Siam Square Thai Cuisine (290 Main Street): Veggie spring rolls and green curry are favorites.
Fiesta Bar & Grill (284 Main Street): The hibiscus margarita is made in-house and delicious.
SoCo Creamery (5 Railroad Street): Award-winning ice cream to round out your day.
Los Lopez Taco Truck: Casual Mexican fare, perfect for a quick snack or late lunch after your hike.
Agaves Mexican Grill: Another fantastic Mexican spot with hearty portions and fresh ingredients—great for lunch or dinner after your adventure.
Optional Scenic Stop: Bartholomew’s Cobble
On your way back to Connecticut, veer right on Route 7A toward Bartholomew’s Cobble in Sheffield:
Trail Highlight: Tractor Path (~1.3 miles) gradually climbs to Hurlburt’s Hill, offering sweeping views of the Housatonic River Valley.
Fee: $5 if not a member.
Perfect Timing: Late afternoon for sunset views after your hike.
Practical Tips & Logistics
Trail Safety: Watch for slick rocks on Hickey Trail and wear traction if needed.
Gear: Lightweight, moisture-wicking layers are key. [Base Layer Guide]
Parking: Monument Mountain kiosk; peak season may require arriving early.
Timing: Plan about 2–3 hours for the hike, longer if exploring the summit or Devil’s Pulpit.
Day Trip Summary
Grab breakfast or a smoothie at Rio Cafe, Fuel, or Bear Butter.
Hike Monument Mountain, summit Peeskawso Peak, enjoy Devil’s Pulpit.
Refuel at Barrington Brewery, Fiesta Bar & Grill, or The Well.
Optional stop at Bartholomew’s Cobble for sunset views.
Monument Mountain + Great Barrington makes a perfect Berkshire day trip. With scenic hikes, local food, and a touch of adventure, it’s a full day of memories.
Happy Hiking!
Agaves Mexican Grill
389 Stockbridge Rd.
Great Barrington, MA 01230
Barrington Brewery & Restaurant
420 Stockbridge Road Unit 4
Great Barrington, MA 01230
Bartholomew’s Cobble
105 Weatogue Road
Sheffield, MA 01257
Bear Butter
323 Main Street
Great Barrington, MA 01230
Cafe Holli
200 Main St.
Great Barrington, MA 01230
Fiesta Bar and Grill
284 Main St Bldg. II
Great Barrington, MA 01230
Fuel
293 Main Street
Great Barrington, MA 01230
Great Barrington Bagel Company
777 S Main Street # 1
Great Barrington, MA 01230
Los Lopez Taco Truck
198 Main St.
Great Barrington, MA 01230
Monument Mountain
545 Stockbridge Road, Route 7
Great Barrington, MA 01230
Length - around 6 miles total
Hickey Trail
Mohican Monument Trail
Peeskawso Peak Trail
Cross Over Trail
Willow's Trail
Height - 1,642 feet
Time - Two to three hours
Difficulty - Moderate to Strenuous
Features - Rock outcroppings, views, and a small waterfall
Rio Cafe
403 Stockbridge Road
Great Barrington, MA 01230
Siam Square Thai Cuisine
290 Main Street
Great Barrington, MA 01230
SoCo Creamery
5 Railroad Street
Great Barrington, MA 01230
The Well Restaurant & Bar
312 Main Street
Great Barrington, MA 01230
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