Monument Mountain Hike: Why It’s the Best in the Berkshires!

Monument Mountain

The Monument Mountain hike is a must if you’re visiting the Berkshires in Massachusetts! This short, but beautiful hike will take you up and over Great Barrington for incredible views of the area. Join us on the Monument Mountain trails to enjoy the great outdoors of Western Massachusetts.

Massachusetts Travel Inspiration 

Monument Mountain Hike Info

If you can only do one hike while visiting the Berkshires this is one we highly recommend! The trails are well maintained and there are multiple Monument Mountain trails for different skill levels.

From above you’ll have stunning views of the Housatonic River Valley and Taconic Mountains. Below are some general tips to know before your visit to Monument Mountain.

Distance: 2.6+ Miles Depending on the Trails
Time Needed: 1.5 Hours
Trail Hours: Sunrise to Sunset
Pack: Water, Sunblock, and Snacks for the Top

Hiking Monument Mountain Info

How to Get to the Monument Mountain Hike

The Monument Mountain hike is located off of Route 7 in the gorgeous Berkshires of Western Massachusetts. Its location is directly between Stockbridge and Great Barrington with the town centers both under 10 minutes away.

There is a small parking area with lots of room. However, as one of the most popular hikes in the area, it can get quite crowded in the summer months. 

One thing to note is that you do have to pay for parking which is a new change that has happened in the last few years. Use the small machine that accepts credit cards to pay $6. This parking for the Monument Mountain hike is good all day. 

Monument Mountain Parking Location

Monument Mountain Massachusetts

Monument Mountain Parking

History of Monument Mountain in the Berkshires

Were you wondering how Monument Mountain got its name? It was actually a sacred site of the Mohican Nation!

The Mohican Native Americans lived in this region for thousands of years before the arrival of the Europeans. Monument Mountain is most likely named after a large stone site at the peak where their prayer offerings were done.

Another fun fact about Monument Mountain Massachusetts is that it has had some very famous visitors over the years. Writers Herman Melville and Nathaniel Hawthorne took the Monument Mountain hike back in 1850.

Legend has it, a storm forced them into a cave which inspired Melville to write the novel Moby Dick. Can you believe there’s so much history to discover at Monument Mountain? 

Monument Mountain History

Best Monument Mountain Trails

Once you’re ready to start the Monument Mountain hike you’ll have two different options from the parking lot. The trail to the right is called the Hickory Trail, and to the left you will find the Indian Monument Trail. 

Indian Monument Trail: The fist of the Monument Mountain trails is more of a gradual climb to the top. It is known to be less difficult than Hickory, but the path is slightly longer. 

Hickory Trail: Also known as the Melville trail, this one is shorter at only 1 mile but comes with a steeper incline. You’re sure to feel this as you get towards the top of the Monument Mountain hike! 

Monument Mountain Trail Map

Peeskawso Peak Trail

Once you’re almost at the summit you will see another trail that diverges from both paths mentioned above. Peeskawso Peak is the trail to to take for the most beautiful views on Monument Mountain in the Berkshires!

Keep in mind that the drop is very steep along the ridge top. Take extra caution near the edges especially if you are doing this section of the Monument Mountain hike with kids.


Peeskawso Peak Trail

Our Recent Monument Mountain Hike 

We’ve experienced hiking Monument Mountain at least a dozen times and it is always amazing! We love how depending on the seasons it will look different each time when you reach the top. 

Luckily our last visit to the Berkshires was during the magical fall season. We hiked up the Hickory trail, cut over to Peeskawso, and took the Indian Monument trail down.

While that might sound a little confusing there are many signs along the path to guide you. This is not a hike you want to miss during the warmer months in the Berkshires!

→ Packing For A Day Hike: 10 Essentials We Always Carry

Monument Mountain Massachusetts Hike

Stunning Views From Monument Mountain MA

The views are incredible from both sides at the top of Monument Mountain Massachusetts. Honestly, for the length and ease of the hike, it’s really one of the most rewarding views in the area.

If you are able to take the Monument Mountain hike in the fall you’ll see the red and orange leaves mixing in beautifully with the rolling green hills. 

There are plenty of rocks and small nooks to find your own lookout spots. We packed some sandwiches and delicious local fall treats which we ate at the top on a perfect autumn afternoon.

Monument Mountain Hike

Have any questions on this article or want to share your own tips for the Monument Mountain hike?  Leave us a comment below!

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar

Where To Stay in The Berkshires

Ultra Luxury – Miraval Berkshires Resort & Spa – Take in some luxury in this historic Wyndhurst Mansion turned resort. Enjoy golfing, spa treatments, and views of the beautiful Berkshire countryside. 

Fun Vacation – Courtyard by Marriott Lenox – Just a quick drive from downtown Lenox, this is the perfect spot to relax after a fun day of exploring. While there are plenty of historic hotels and Airbnb’s in the area, we enjoyed having the modern amenities and swimming pool at the Courtyard by Marriot.

Bed & Breakfast – Chambery Inn – This beautiful bed and breakfast is situated out in the countryside of Lee, but still close enough to walk to local restaurants and shops. You’ll also be just a few miles from attractions such a Tanglewood and Butternut Ski Resort.

Historic Hotel – Red Lion Inn – This historic hotel is a landmark in the town of Stockbridge. Stroll through town which is right at your doorstep, or simply watch the day pass you by while sipping on drinks on the front porch.

For more places to stay in The Berkshires you can explore the latest prices here!


Monument Mountain Hike Guide

New England Travel Planning 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip! 

Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Scenic Boat Tour in Portland Maine! 

 Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

New England Travel

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