As a location to explore the Berkshires of Massachusetts has tons for families to do. If your family likes outdoor activities you should definitely explore the Berkshires. The area is full of small towns with lots of charm, mountains to hike and ski, and natural wonders to discover. Sounds like a great place for a weekend away, right?
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Where are the Berkshires of Massachusetts
The Berkshires encompass the western end of Massachusetts by the New York border. The Berkshire Mountains are actually part of the Green Mountain range in Vermont. However, locals call them “The Berkshires”. The Mass Pike is the main thoroughfare through this region from east to west and Rt 7 for north to south.
Small Towns in the Berkshires
If you love small-town charm then the Berkshires are for you. My girls and I can spend a whole day just meandering in and out of mom-and-pop shops to see what gems they are offering. In the course of our travels, we have found wonderful gifts for others and fun treasures for ourselves.
Of course, we never miss a chance to stop for some locally made chocolates or ice cream. Yeah, well we’re on a holiday after all. We love to see what flavors the different shops have. And don’t get me started on penny candy. I love seeing all the candy from my youth. We generally get a bag of penny candy to share.
Stockbridge is definitely a town you shouldn’t miss. They have a few fun stores to shop in and of course, get candy and ice cream. Their candy store is even named “Peace, Love and Chocolate”, with a name like that you have to stop in. Don’t miss going onto Elm Street as well. They have even more shops to explore.
In the town of Pittsfield, you can take a ride on The Berkshire Carousel. This carousel has been restored and is inside so no matter the weather you can have a ride. If you have a train lover in your group don’t miss the Berkshire Scenic Railway Museum. You can go into an old fashion train station and even ride in an old “Lenox Jitney” on the museum grounds. If however, you would like a longer train ride you can take a 1-hour roundtrip ride on the Historic Adams Branch.
Natural Bridge
In North Adams, is the Natural Bridge State Park. It is a marble bridge carved by glacial runoff over 550 million years ago. Part of an old quarry but now a state park you can explore, this area has beautiful backdrops for photos. The river that runs through the park doesn’t flow as strong as it once did but I’m sure it’s still eroding the rocks.
Looking down into the river you can see the curves of the rock and how the river has made its way through them. The curves are quite spectacular.
When we visited the top parking lot was full so we had to park at the entrance road. However, the walk up is beautiful and we got to see the waterfall along the way. It’s not a huge waterfall but pretty enough to stop and photograph.
Within the park can also see the remnant of the old marble quarry. The old dam is a lovely waterfall with a display explaining the workings of the quarry.
Mount Greylock
Mount Greylock is the highest point in Massachusetts at 3,491 feet and the views from the top are spectacular. There are several places along the auto road to park and hike up. If you chose to drive all the way up just note there may be a lot of traffic and you may not get a parking spot at the top.
The memorial at the top is the Veterans War Memorial. The original memorial built-in 1932 was rebuilt in 2017. At the top of the memorial is a beacon that shines every night. From the towns of North Adams and Adams, it looks like a lighthouse.
There is a visitor’s center at the top along with a topography map showing you the area and monument. Normally the memorial is open and you can walk up the circular staircase to the top. However, due to Covid, it is currently closed.
Jiminy Peak Resort
No matter what season you go to the Berkshires, there is always something to do at Jiminy Peak. Of course in winter there is great skiing with over 167 acres of skiing. The mountain boasts 9 lifts, a rise of 1150 ft, 3 terrain parks, over 96% snowmaking coverage with their longest run being 2 miles long, you will have a great day of skiing.
In the summer, after Memorial Day the resort turns into a summer playground for those who love the outdoors. The resort has an aerial adventure park as well as a mountain adventure park. There is also mountain biking and hiking.
Norman Rockwell Museum
This museum really resonates with my younger daughter. She loves seeing all these paintings of everyday life. Rockwell’s paintings are quite mesmerizing as you walk through the museum. I love the different collections especially the cartoon section and the unity collection. My daughter loved the Saturday Evening Post and I agree it is another wonderful collection.
Don’t miss walking around the grounds of the estate. The sweeping views of the hills and valleys of the Berkshires are lovely as is the river. Of course, we walked down to the river and found a wonderful old bridge. It is closed to car traffic but you can walk on it and enjoy the river a bit.
The most wonderful thing that I can see that has come from Covid is all these new online experiences. Well, the Norman Rockwell Museum has a wonderful online class. You can take free sketching classes based on his artwork. The first one is based on his painting “A visit to the vet” and the artist shows you how to draw a dog. I like that they not only show you how to draw the subject but also how to really make it look life-like. After all, isn’t that what we want out of our drawings? I know we do.
Berkshire Botanical Gardens
If you visit the Berkshires late spring through fall definitely visit the Berkshire Botanical Gardens. What a beautiful outdoor space with lovely gardens all around you. With 33 different areas to explore you are sure to find something you love.
Personally, we have always loved the children’s gardens. However, in this garden, I really love the herb garden as well as the edible garden. My favorite, however, is the primrose walk and the pond gardens. My parents had a pond at our house and I love seeing the water lilies and fish as well as the frogs that came to stay.
Waterfalls in the Berkshires
There are a number of waterfalls you can hike to in the Berkshires, including Massachusetts’s tallest waterfall, Bash Bish Falls. There are two parking areas to access Bash Bish Falls, one from Massachusetts and the other from the New York side.
From the New York side, you enter from the lower parking lot and hike along the Bash Bish brook until you reach the falls. If you hike from the Mass side you will need to navigate lots of steps down to the falls.
If you are looking for a moderate hike with a big payoff hike Race Brook Falls in Sheffield, MA. The views will not disappoint you nor will the waterfall itself. This is a heavy traffic trail but it’s worth it for this waterfall.
Another great hike is The Cascades Trail. For this hike you need to park at the Brayton Elementary School and follow the signs to the trailhead, you can not park on the streets right next to the trailhead. Once in the woods, you are rewarded by a beautiful river walk and forest. You do need to cross the river on rocks so wear good shoes. In autumn when we visited it was flowing but not as much as in spring or after a good rainfall so plan accordingly. Still worth the hike though.
If you really love waterfalls you should explore these 7 waterfalls in Vermont.
For more hiking try exploring these Massachusetts state parks.
Hikes and Lookouts in the Berkshires
Olivia’s Overlook near West Stockbridge has a beautiful hilltop view over the Stockbridge Bowl which is a local pond. The valley view with the mountains beyond is worth a stop. You can also cross the road and hike up to the top of the mountain by the Charcoal trail.
Adams Overlook looks down on the town of Adams. It is located on Rockwell Rd and has a pull-off for you to park and stretch your legs. If the weather is good you can see for 60 to 70 miles away.
Along Rt 2 in North Adams is a little gift shop call Wigwam Western Summit. They have coffee and some made-up sandwiches along with the trinket gifts. The reason for your stop will be the view though. They even have a little bench with a sign that says “Welcome to America’s Switzerland”. It made me laugh.
For a family friendly hike I’d suggest Stevens Glen Trail. There is a bench at the end for you to relax before heading back out.
Housatonic River Walk is a wonderful path along the river just off Main St in Great Barrington. You can get a nice meal then have a stroll along the river to walk off the calories.
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Final Thoughts on Visiting the Berkshires
As you can see the Berkshires in Massachusetts are a wonderful place to explore nature. It is quickly becoming a favorite place for my family to visit. We have yet to hike all the state parks so I know we will be back. I also want to visit Stockbridge during their Christmas celebrations. They really do it up.
Have you been to the Berkshires? If so what was your favorite thing to do or place to visit?
The Norman Rockwell Museum would be cool! Or the botanical gardens. Or everything lol
Yes, the Berkshires have a lot to explore.
I’m so glad you wrote this! As an American (not from the East coast), I’d definitely heard of the Berkshires, but never knew where it was! Looks beautiful .. I’d love to visit that general store (i know there are tons and tons of goodies in there!) and the Norman Rockwell museum. Otherwise, just a good wander around enjoying those gorgeous autumn colors would be fun too. 🙂
I see you are another lover of general stores. We can’t seem to pass them up on our travels.
I really need to spend more time in the Berkshires! I’d love to go to the Norman Rockwell Museum.
I visited Mt Greylock during the fall years ago, it was so beautiful!
Yes, Mt. Greylock is amazing in the fall. I was honestly surprised by the Norman Rockwell Museum. There are so many different collections.
The Berkshires look gorgeous showing off those fall colours! Would definitely love to hike there!
Yes, Marianne, your family would definitely love the hikes in the Berkshires.
What a beautiful area! The Berkshires look like a great place to explore.
Definitely, a great place to explore.
I would love to explore and find all this natural beauty in the Berkshires, MA. The views are gorgeous and especially love the waterfalls.
Yes, we really enjoyed finding the waterfalls, not too difficult and very rewarding.
What a great article! I have a friend from Pittsfield in The Berkshires. She’s always told me it’s beautiful and your photos are showing me that she’s right! I’d love to visit during autumn for the fall colors and do some of those hikes. Also love the look of the waterfalls!
The Berkshires are amazing in the fall, one of the best times to visit.
Sadly I never got to the Berkshires when I lived in Massachussetts. I think I will have to make a road trip now after reading this.
Yes, exploring the Berkshire in a road trip is ideal.
wow! Beautiful! I’ve never been to the Berkshires, but it’s so gorgeous!
Yes, I agree the Berkshires are beautiful.
The Berkshires look like a great place to experience nature. The Fall with all the autumn colored leaves must look amazing. The War Memorial got me too, I thought it was an unique lighthouse!
Yes, the war memorial is a sort of inland lighthouse, very beautiful at night.
I never realized what a wide variety of things there are to do in the Berkshires. And it touches on everything I love to do too, from hiking to beautiful waterfalls to shopping in quaint little shops to exploring a new museum… we are definitely going to have to plan a trip. Thanks for sharing!
I’m glad you discovered the Berkshires.
What a beautiful area! We had to postpone our east coast trip last summer, but I’m hoping to go in the next couple of years. I’d love to visit the shops in the Berkshires, and the nature trails look fun, too. Someday!
Definitely replan your east coast trip. I’m sure you will love it here.
Can I live in those mountais with those views? I could spend a day just visiting the downtown local shops and at least an hour in the general store. I haven’t heard of these mountains but Norman Rockwell museum would be a great addition to the trip.
Yes, my kids and I really enjoy going into the local shops as well. It was definitely a fun trip for shopping.
I’ve never been to the Berkshires in Massachusetts, but thinking I should. I would love to go hiking here…the views are stunning!
Yes, the views are quite amazing. And every time we hiked to a new place the view was different but just as special.
I cannot wait to visit The Berkshires! Would love to visit the Norman Rockwell Museum!
The Norman Rockwell Museum is very special. Next time I hope they have his studio open.
We loved our time in the Berkshires. We are looking forward to going back this fall or perhaps at Christmas time.
That sounds lovely. I would love to see downtown Stockbridge lit up at Christmas.
So much to do in the Berkshires! I’d love a peek inside the Norman Rockwell museum.
I was surprised by the number of different collections that had. It was a fun museum.
The Berkshires look like a beautiful place to visit. There is so much to do and see.
I absolutely agree. In fact, I just found a few new restaurants and even a brewery we should check out next time we go.