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Writer's pictureBirch & Bambi

Day Trip to Great Barrington & Hiking Monument Mountain

Updated: Oct 25

I live in northwest Connecticut, so a day trip to Great Barrington, Massachusetts is about a forty-five minute drive. I normally take route 7 because it's a pretty ride through the woods and CT 'mountains'. When you cross the state border into Massachusetts you enter Sheffield. This is a perfect town for anyone who likes antiquing. Keep following route 7 and you will soon enter Great Barrington.


Read below for great day trip itinerary ideas, including links and details!


view of devils pulpit, park of the Monument Mountain hike in Great Barrington, Massachusetts. Located in New England.
view of devils pulpit, park of the Monument Mountain hike in Great Barrington, Massachusetts. Located in New England.

Depending on what I have planned for the day, I pack food/snacks or I grab food in the area. If I plan to eat on a trip through Great Barrington, there are a few restaurants I would recommend! Before I hike I don’t like to eat anything heavy, but want something to give me enough energy to hike. Rio Cafe is the perfect spot to stop and very close to the Monument Mountain parking lot. They have indoor dining or outdoor dining beside a peaceful river. I eat vegetarian so my go-to would be a fresh fruit smoothie or the vegetarian chili omelet. They have a ton of other vegetarian dishes to choose from. For smoothies you can choose from specialty smoothies or you can make your own and they have SO many options. If you would rather have a coffee, stop at Fuel on Main Street. Not only is their coffee delicious, they offer a wide variety of local goods and live music. Another great smoothie option is Bear Butter. I am still dreaming of the Healthy Elvis smoothie I got last time I was up there.



After breakfast, drive three minutes up the road to the Monument Mountain parking lot. You will use a kiosk to pay for parking. I've hiked Monument Mountain almost every season of the year, but have not visited during fall. I'm sure it's beautiful up there! This hike may not be the longest, but it can be tough and dangerous in some spots. I wouldn't recommend this hike for beginners or large groups of people. If you bring children make sure they stay on trail and close by. Unfortunately, many hikers have been seriously injured on this mountain. Another thing to keep in mind - pets on leashes are allowed and I have brought my dogs once, but the summit was not a fun place to be with them. Use caution!!



Monument Mountain has just under six miles of trails. You can create your own trail depending on what you are in the mood to see! The good thing about hiking Monument Mountain is the trails and markers are well taken care of. Keep an eye out for them as you hike to be sure you are on the correct trail. I have not hiked Willow's Trail (1.8 miles) or the Cross Over Trail (.7 miles) The Mohican Trail is the “easiest” trail up the mountain and will bring you up to Inscription Rock after about 1.6 miles. You then choose between Hickey Trail or Peeskawso Peak Trail. Hickey Trail is going to bring you back down the mountain to the parking lot in .9 miles. This trail can be steep and gets VERY slippery in the Winter/beginning of Spring. I don't recommend this without spikes or something similar. There are ravines off the side of the trail in spots, with the trail iced over it gets nerve-racking here. On the plus side, the highlight of this trail is the waterfall you will pass! Keep an eye on the right when you’re coming down. You will be able to walk right up to it and go right under that rock formation and look behind the ice formation!



If you don’t want to head back down the mountain yet, get ready to climb up to the 1,642 foot summit called Peeskawso Peak via the Peeskawso Peak Trail. This trail is about .7 miles and will connect you back to the Mohican Monument Trail to bring you down the mountain. The top of Monument Mountain is very steep and full of jagged rock formations, go slow and watch your step. On a good day you may be able to see the border of Vermont! At the summit you pretty much have a 360 degree view. The side you can’t see so much is just a few steps away. As you hike the Peeskawso Peak trail make sure to watch for the Devil’s Pulpit marker. It's hidden off the trail and can easily go unnoticed. Again, please be very careful here the drop offs are HUGE. This is my absolute favorite park of the hike, I love the rocky outcropping. By this point I usually worked up an appetite, so I head back to the car and in the direction I came from. The first restaurant on the left side of the road is Barrington Brewery & Restaurant.



Barrington Brewery & Restaurant is the perfect spot to relax after hiking. They've been open over twenty five years and are the first brewery in the East coast to have solar-heated water for brewing beer! My favorite beer is their Raspberry Ale. They have five other house brewed beer options on tap. I love fresh pretzels, so that's typically my starter.


If you would rather have pizza, try the sourdough recipes from Baba Louie's. I had the Dirty Brutta which is roasted potatoes, pesto, roasted garlic parmesan and basil. My husband created his own pizza. If you are in the mood for a bagel or sandwich The Great Barrington Bagel Company has unique options. I love the tornado bagel with olive pimento cream cheese. One of my favorite restaurants is The Well on Main Street, we had some of the best nachos here! Siam Square Thai Cuisine is another delicious stop on Main Street. I loved their veggies spring rolls and green curry. If you are craving some Mexican food, the best spot is Fiesta Bar and Grill. Every time I go their food is amazing and the hibiscus margarita is delicious, they make their syrup in house! Dessert time? Get some ice cream at SoCo Creamery. This ice cream shop has won multiple awards throughout the years.



If you are traveling back to Connecticut I have one more great stop. Follow Route 7 south through Sheffield, Massachusetts for about eighteen minutes and there will be a veer to the right for route 7a. Take this road to head to Bartholomew’s Cobble Reservation. This is a great spot for a picnic during the day as well! There' s a small fee when you visit, $5 if you are not a member. By this point in your day, if you plan it right, you have the chance to see a beautiful sunset! There are about five miles of trails at the reservation, but the Tractor Path is an easy 1.3 mile trail that gradually leads to Hurlburt’s Hill for a beautiful wide open view of the Housatonic River Valley.


view from hurburts hill at bartholomew's cobble in massachusetts. part of new england.
view from hurlburts hill at bartholomew's cobble in massachusetts. part of new england.

After your long day, head home and relax! Hopefully this guide through Great Barrington, Massachusetts and Monument Mountain is helpful, below is a list of addresses and details for each place I mentioned.


Have you ever hiked Monument Mountain? What restaurants have you been to in the area? I would love to hear any questions or experiences you had!


Happy Hiking!



Baba Louie's Sourdough Pizza

42/44 Railroad Street

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


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


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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