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Find the Natural Beauty in the Berkshires, MA

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.

The Berkshires
A great lookout

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.

General Store in the Berkshires
The General Store in Stockbridge

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.

ice cream in the Berkshires
Trying the local ice cream

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.

candy shop in the Berkshires
Peace, Love and Chocolate’s offerings.

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.

natural bridge in the Berkshires
The natural bridge is just behind her

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.

state park in the Berkshires
You can see how the water has carved the stone

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.

state park in the Berkshires
Quarry Dam

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.

highest point in the Berkshires
Mount Greylock Veterans War Memorial

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.

view in the Berkshires
Can’t beat that view

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.

Norman Rockwell in Berkshires
Norman Rockwell Museum

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.

Norman Rockwell in Berkshires
Outdoor art sculpture at the Norman Rockwell Museum

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.

Berkshire Botanical Gardens
Photo by Berkshire Botanical Gardens

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.

Bash Bish 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.

Race Brook Falls in the Berkshires
Race Brook Falls

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.

Cascades Trail in the Berkshires
Cascades Trail

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.

Olivia's Outlook in the Berkshires
Olivia’s Outlook

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.

Adams Overlook in the Berkshires
Adams Overlook

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
Housatonic River Walk

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.

Pin for Later

Explore in the Berkshires
Explore in the Berkshires
natural beauty in the Berkshires
Finding the Natural Beauty in the Berkshires

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?

This Post Has 36 Comments

  1. Alexis Farmer

    The Norman Rockwell Museum would be cool! Or the botanical gardens. Or everything lol

    1. Leeanne

      Yes, the Berkshires have a lot to explore.

  2. lannie

    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. 🙂

    1. Leeanne

      I see you are another lover of general stores. We can’t seem to pass them up on our travels.

  3. Sue

    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!

    1. Leeanne

      Yes, Mt. Greylock is amazing in the fall. I was honestly surprised by the Norman Rockwell Museum. There are so many different collections.

  4. Marianne

    The Berkshires look gorgeous showing off those fall colours! Would definitely love to hike there!

    1. Leeanne

      Yes, Marianne, your family would definitely love the hikes in the Berkshires.

  5. Lisa Manderino

    What a beautiful area! The Berkshires look like a great place to explore.

    1. Leeanne

      Definitely, a great place to explore.

  6. kmf

    I would love to explore and find all this natural beauty in the Berkshires, MA. The views are gorgeous and especially love the waterfalls.

    1. Leeanne

      Yes, we really enjoyed finding the waterfalls, not too difficult and very rewarding.

  7. Becky Exploring

    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!

    1. Leeanne

      The Berkshires are amazing in the fall, one of the best times to visit.

  8. alison netzer

    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.

    1. Leeanne

      Yes, exploring the Berkshire in a road trip is ideal.

  9. Kendra

    wow! Beautiful! I’ve never been to the Berkshires, but it’s so gorgeous!

    1. Leeanne

      Yes, I agree the Berkshires are beautiful.

  10. Jennifer

    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!

    1. Leeanne

      Yes, the war memorial is a sort of inland lighthouse, very beautiful at night.

  11. Alison

    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!

    1. Leeanne

      I’m glad you discovered the Berkshires.

  12. Stacey Billingsley

    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!

    1. Leeanne

      Definitely replan your east coast trip. I’m sure you will love it here.

  13. Carey

    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.

    1. Leeanne

      Yes, my kids and I really enjoy going into the local shops as well. It was definitely a fun trip for shopping.

  14. Karen

    I’ve never been to the Berkshires in Massachusetts, but thinking I should. I would love to go hiking here…the views are stunning!

    1. Leeanne

      Yes, the views are quite amazing. And every time we hiked to a new place the view was different but just as special.

  15. Julie Gazdecki

    I cannot wait to visit The Berkshires! Would love to visit the Norman Rockwell Museum!

    1. Leeanne

      The Norman Rockwell Museum is very special. Next time I hope they have his studio open.

  16. heather J jandrue

    We loved our time in the Berkshires. We are looking forward to going back this fall or perhaps at Christmas time.

    1. Leeanne

      That sounds lovely. I would love to see downtown Stockbridge lit up at Christmas.

  17. Cindy

    So much to do in the Berkshires! I’d love a peek inside the Norman Rockwell museum.

    1. Leeanne

      I was surprised by the number of different collections that had. It was a fun museum.

  18. Lisa Manderino

    The Berkshires look like a beautiful place to visit. There is so much to do and see.

    1. Leeanne

      I absolutely agree. In fact, I just found a few new restaurants and even a brewery we should check out next time we go.

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