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14 Ideas for Fresh Air and Fun

Posted on July 09, 2020Written by Elizabeth Nelson
Updated on July 09, 2020

Path to Greylock

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Western Massachusetts Getaways!

Mount GreylockIn ten years of running this Boston-based travel blog, my articles about vacations and day trips in the Berkshire Mountains have proven mighty popular. Now that so many of us are yearning for fresh air and nature, it seems the perfect time to compile these together into 14 travel ideas.

Berkshires, MA Attractions

Western Massachusetts offers delights for all ages! Many of these ideas are outside in nature and provide lots of fresh air… and most are FREE! See what’s on offer…

Mount Greylock: The Highest Point in Massachusetts!

What’s the tallest mountain in MA? This one! And good news — you can drive right up to the top. The views of New England are incredible from the summit!

Bash Bish Falls: Read This Before Hiking

From the highest mountain in Massachusetts, let’s move to the tallest single drop waterfall: Bash Bish! Just make sure to follow my advice in this linked article if you go, because there are two different entrances with very different hiking experiences — and I don’t want you to make the same mistake we did!

See Tiny Planes at Great Barrington Airport

Watching vibrantly colored small planes take off is one of our family’s favorite pastimes in the Berkshires. Walter J. Koladza Airport is a friendly, fascinating spot that is well worth an afternoon stop.

MASS MoCA: A Perfect Art Museum

This sprawling building redefines what a museum can be, showing modern art of all sizes and forms. You could spend a full day here — or more — and satisfy kids and adults alike. Don’t miss the musical instrument room!

The Red Lion Inn, Stockbridge, MA

This famed historic hotel is the definition of unique. Every inch of the building is packed with character and curios. Learn the full story and see pictures here — and consider stopping by for outdoor patio dining.

Alpaca Farm Fun in Western MA!

FLUFFY ALPACAS!!! Watch the wonderful beasts munch grass for free, and pick up some fresh maple syrup (or alpaca wool socks) at the sweet store on site.

The Clark Museum’s Magic

One of the most famous museums in Western Massachusetts is The Clark: a collection of art which soothes the soul and makes the imagination soar. I wrote this article about how visiting it with my brother helped bring us closer together — and it might do the same for you and your loved ones.

Where to Eat in Williamstown, MA

This country store knocked our socks off with its delicious sandwiches, pizza, and outdoor seating — with mountain views! It’s an ideal place to eat with kids, too.

A Hidden Hike in the Berkshires

Learn about Cheshire Cobbles: a relaxed hike with an outlook near Cheshire, MA. This article also describes the Bed and Breakfast nearby which we loved, and though it’s now under new management, it still gets great reviews.

Bike Paths and Farm Stands by Cheshire, MA

The Ashuwillticook Rail Trail in Western Massachusetts is ideal for renting a bike (or bringing your own) to pass pastoral views and country stores.

Enjoy Northampton, MA

Though the focus of this article is Western Massachusetts, if you’re driving from Boston you’ll pass through Hampshire County after two hours, and I can’t resist recommending a peek around the charming town of Northampton.

Fun Activities Near Amherst, MA

From the Eric Carle Museum of Picture Book Art, to a free and fabulous indoor playground and farm (Mill 180 Park), to epic apple cider donuts, consider at least one of these attractions in Hampshire County an hour from the Berkshires.

Southbridge, MA for a Stop on Your Trip

Some of the best Barbecue I’ve ever eaten is found in Sturbridge, en route to Western Massachusetts. See where to find it here, along with a fascinating optical museum and great coffee in nearby Southbridge.

Old Sturbridge Village, MA

For those driving from Boston to the Berkshires, remember that just an hour outside the city sits famed Old Sturbridge Village: the absolutely charming 18th century town and farm which is an interactive outdoor museum to delight all ages. I was stunned by how moving and beautiful I found it!

Where to Stay in Western MA?

Ok, so these articles have convinced you to visit the Berkshires… so where to stay? Here are some suggestions (in the form of affiliate links which you may choose to use to provide a commission at no extra cost to you). The first option is to browse these ratings of hotels to see if any fit your location, cost, and style desires.

While I’ve enjoyed many a hotel and inn in Western Massachusetts, my current favorite option now that I have young kids is to rent a whole house (click here to see the company I use) so that extended family can all stay together. It often ends up being much more affordable and convenient than a hotel, though each has its perks.

Which Berkshires Spots Do YOU Love?

These ideas only scratch the surface of the MANY wonderful things to do and see in Western Massachusetts. I didn’t even touch yet on Tanglewood, the Norman Rockwell Museum, charming small towns, hidden lakes, and goat yoga — but it’s a start! What are your votes for attractions in this area? Do share!

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