Monument Mountain Hike in Great Barrington, MA: Trail Guide, Parking & Best Views
- Amber in New England
- Jul 25, 2021
- 6 min read
Updated: Mar 21
If you're looking for a short hike in the Berkshires with big views, Monument Mountain in Great Barrington, MA should absolutely be at the top of your list.
At only about 2.5 miles, it’s not a long hike, but it packs a lot into a short distance. Between rocky scrambles, exposed viewpoints, and the dramatic overlook known as Devil’s Pulpit, Monument Mountain feels like a quick rugged adventure.
I hike a lot around northwest Connecticut and the Berkshires, and this trail stands out because it hits that perfect balance: short distance, interesting terrain, and a rewarding summit.
Another bonus? Great Barrington is right down the road, so once you finish the hike you’re minutes away from coffee, lunch, or ice cream.
In this guide, I’ll cover exactly how to hike Monument Mountain, including the best loop to take, seasonal tips, and the secret to navigating the notoriously crowded parking lot.
(Quick Disclosure: This guide contains affiliate links. I may earn a small commission if you buy through them, at no extra cost to you.)
Monument Mountain Hike: Quick Info
Location: Great Barrington, Massachusetts
Distance: ~2.5 miles (Loop)
Elevation Gain: ~700 ft
Difficulty: Moderate (Includes some rocky scrambling)
Time: 2–3 hours
Parking Fee: ~$6 per car (Free for Trustees members)
Dogs Allowed: Yes, but must be leashed (be very careful near the summit drop-offs).
Monument Mountain Reservation Parking
Let's address the most stressful part of this hike first: the parking.
Because this is one of the most popular trails in the Berkshires, the Monument Mountain Reservation parking lot (located right on Route 7) fills up incredibly fast. The reservation is managed by The Trustees of Reservations, and they are strict about capacity.
Fee: Payment is via a self-service kiosk (around $6).
The Warning: Roadside parking on Route 7 is strictly prohibited and heavily ticketed.
The Local Secret: If you are visiting on a summer weekend or during peak fall foliage, you must plan to arrive before 9:00 AM. By mid-morning, the lot is at capacity, and you will be turned away.
Parking for Monument Mountain is located at the Monument Mountain Reservation lot off Route 7 in Great Barrington.
The Trail Guide: Mohican Trail → Peeskawso Peak → Hickey Trail
The most popular way to hike Monument Mountain is as a loop using the Mohican Monument Trail, Peeskawso Peak Trail, and Hickey Trail.
This route is roughly 2.5 miles total and usually takes around 2 hours, depending on how long you spend enjoying the views.
Start: Mohican Monument Trail (Blue)
The hike begins on the Mohican Monument Trail, which starts as a gradual climb through the forest.
The first section follows what used to be a carriage road, so the grade is relatively gentle compared to the rest of the hike. It’s a nice warm-up before the terrain gets steeper and rockier.
Peeskawso Peak & Devil’s Pulpit
As you approach the summit area, the trail becomes more rugged.
The final stretch toward Peeskawso Peak involves climbing over large boulders, and in a few places you’ll probably use your hands to help scramble up. It’s not technical, but it’s definitely more interesting than a typical forest trail.
Right before the summit you’ll reach one of the most famous features of the hike: Devil’s Pulpit.
This narrow rock outcrop juts out dramatically from the mountain, with steep drop-offs on either side. The views here are beautiful, but it’s definitely a spot where you want to slow down and watch your footing.
On a clear day you can see across the Berkshires and even into Vermont.
Descent: Hickey Trail (Yellow)
To complete the loop, you’ll descend via the Hickey Trail.
This section is steeper as well, with stone steps, exposed roots, and rocky sections that can be slippery if the trail is wet.
Trekking poles can be helpful here, especially for protecting your knees on the way down.
There’s also a small seasonal waterfall along this trail that can be a nice bonus depending on the time of year.
(Looking for other easy-to-moderate Connecticut trails? See our CT Hikes guide.)
Plan a Day Trip to Great Barrington
Because Monument Mountain sits just over the border from northwest Connecticut, it is the ultimate anchor for a Berkshires day trip. After burning those calories on the rocky summit, head straight into downtown Great Barrington (less than 10 minutes away).
Pre-Hike Coffee & Breakfast
One of the best parts about hiking Monument Mountain is that Great Barrington is right down the road, which means great coffee and breakfast options before your hike.
Some good spots to check out:
Fuel Coffee Shop – A popular Main Street spot for coffee, breakfast sandwiches, and pastries. They often have live music in the evenings too.
Bear Butter – Known for smoothies and healthy breakfast options. The Healthy Elvis smoothie is a great portable trail snack.
Cafe Holli – A quieter café with good coffee and baked goods.
Great Barrington Bagel Company – If you want something filling before the hike, their bagels and breakfast sandwiches are a solid option.
Even though the hike isn’t long, it’s still a good idea to bring water and a small snack with you.
Post-Hike Lunch & Food in Great Barrington
After the hike, you’re only a few minutes from downtown Great Barrington, which has a surprising number of great food options for a small town.
Some favorites nearby:
Barrington Brewery & Restaurant – A classic post-hike stop with house-brewed beer and good comfort food. The giant pretzel is perfect after a hike.
The Well – Casual spot with great nachos and a relaxed atmosphere.
Siam Square Thai Cuisine – Excellent Thai food if you’re craving something different.
Fiesta Bar & Grill – Big portions and great margaritas.
SoCo Creamery – If it’s summer, an ice cream here is basically mandatory.
Los Lopez Taco Truck – Great quick tacos if you want something fast.
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.
Nearby Scenic Stop: Bartholomew’s Cobble
If you still have energy after hiking Monument Mountain, a great nearby stop is Bartholomew’s Cobble in Sheffield.
This nature reserve has beautiful views over the Housatonic River Valley and a short hike that’s perfect for sunset.
A popular option is the Tractor Path to Hurlburt’s Hill, which is about 1.3 miles round trip and offers a wide scenic overlook.
Entry is around $5 for non-members, and the late afternoon light here can be really beautiful.
Monument Mountain Seasonal Hiking Tips
New England hiking conditions change a lot throughout the year, so here are a few seasonal tips for Monument Mountain.
Winter
Trails can be icy, especially near Devil’s Pulpit and the rocky summit area.
Microspikes or other traction devices are strongly recommended. Dress in layers and bring extra water even though the hike is short.
Spring
Spring can mean muddy trails and slippery rocks, especially after snowmelt.
Waterproof boots are helpful this time of year, and the small waterfall along Hickey Trail is often flowing nicely.
Summer
Summer is the most popular time to hike Monument Mountain.
Bring plenty of water and try to start early to avoid the midday heat. The exposed rock sections near the summit can get hot on sunny days.
Fall
Fall foliage in the Berkshires is incredible, but this is also the busiest season for the trail.
Arrive early to secure parking, and watch your footing on leaves that can make rocks slippery.
Is Monument Mountain Worth Hiking?
Yes! Especially if you like short hikes with big rewards.
In less than three miles you get:
forest trails
rocky scrambling
exposed viewpoints
one of the most dramatic overlooks in the Berkshires
It’s also one of the few hikes where you can finish the trail and be eating lunch in town ten minutes later.
If you’re visiting the Berkshires or driving through western Massachusetts, Monument Mountain is easily one of the best quick hikes in the area.
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
How difficult is Monument Mountain?
Monument Mountain is considered moderate, but some sections feel more strenuous due to rocky scrambling and steep areas.
How long does the Monument Mountain hike take?
Most hikers complete the loop in 2–3 hours, depending on pace and how long they spend enjoying the views.
Can dogs hike Monument Mountain?
Yes, dogs are allowed but must be kept on a leash. Be especially careful near Devil’s Pulpit where the trail runs close to steep drop-offs.
Where do you park for Monument Mountain?
Parking is at the Monument Mountain Reservation lot on Route 7 in Great Barrington. There is a small parking fee for non-members.
More Hikes Near Monument Mountain
If you're exploring this part of New England, there are several great hikes nearby.
Just south of the Berkshires, Northwest Connecticut has some of the best short hikes in New England, short hikes many with beautiful views and quiet trails.
You can also build a full day trip around Litchfield County, combining a morning hike with small towns, scenic drives, and local restaurants.
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