Hiking Monument Mountain: Guide to the Best Hike in the Berkshires

Monument Mountain

Hiking Monument Mountain is a must if you’re coming to this area of the Berkshires! 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 hike to enjoy the great outdoors of Western Massachusetts!


Massachusetts Travel Inspiration 

Hiking Monument Mountain 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 hikes for different skill levels. From above you’ll have stunning views of the Housatonic River Valley and Taconic Mountains.

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

Getting to Monument Mountain Massachusetts

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 hiking Monument Mountain is good all day. 

→ Monument Mountain Parking Location on Google Maps

Monument Mountain Massachusetts

Monument Mountain Parking

Monument Mountain History

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. The mountain is most likely named after a large stone monument at the peak where their prayer offerings were done.

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

Monument Mountain History

Hitting the 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: This trail is more of a gradual climb to the top. It is known to be less difficult than the Hickory trail, 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’ll especially feel this as you get towards the top of Monument Mountain! 

Monument Mountain Trail Map

Peeskawso Peak Trail

Once you are almost at the summit you will see another trail that you can reach from both paths mentioned above. This is where you want to be for the most beautiful views on Monument Mountain!

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

Monument Mountain Hike 

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

On our last visit to the Berkshires in the fall 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.

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

Monument Mountain Massachusetts Hike

Enjoy the Stunning Views 

The views are incredible from both sides on the summit 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 do the Monument Mountian hike in the fall you’ll see the red and orange colors pop mixed in with the rolling green hills. 

There are plenty of rocks and small nooks to find your own spot to hang out and take in the views. 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 hiking Monument Mountain or want to share tips from your own day on the trail? 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!


USA Travel Planning 

Massachusetts Guides:  10 Fun Things Stockbridge  – Hancock Shaker VillageClark ArtBerkshire HorseWorksOlivia’s Overlook

 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 Booking.com 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 Sea Cave Kayak Tour in La Jolla California! 

 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

USA Travel

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