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Day Trip - The Berkshires



Discover, enjoy, spend the day!

Massachusetts, hiking, things to do, places to go, day trips, staycation, the berkshires, kid-friendly, family-friendly, roadtrip, hudson valley, stockbridge

The Berkshires is a perfect place to take your family and feel as if you have gone on vacation without ever needing your passport! The towns are small and quaint with lots of amazing hiking, culture and great local eateries! My family has spent many summers in this paradise, hiking to awe inspiring waterfalls and eating on local farms while the sun goes down. Every place you pass looks like a Norman Rockwell painting.



Our first stop in the Berkshires is a little over an hour outside of the Hudson Valley, depending on where you are located, for us it takes 1 hour and 30 minutes to reach the Berkshire Museum in Pittsfield, MA. This museum of natural history boasts an impressive collection that will delight children and adults. From fossils, to mummies, a mini aquarium and lots of hands on exhibits it is one of our favorite New England museums. There is plenty of free parking, lots of places to eat nearby and your children will love the museum's mascot; Wally the Stegosaurus. The museum encourages all guests to take a selfie with him and post it on their Facebook page! You could easily spend a whole day here!



After your fill of history and culture a 20 minute drive south, takes us to the small and charming village of Stockbridge, MA. The Main Street is filled with old fashion markets, art galleries and locally owned gift stores.


Perusing the stores on Main Street is fun in itself but the main attraction to this area is our next stop, Naumkeag Gardens. A short walk from downtown, is the perfect place to explore and take in the gorgeous Berkshire views! Filled with secret gardens, fountains and lots of interesting sculptures my daughter absolutely loved our visit. We ordered a picnic lunch at Elm Street Market, which they pack for you and spent our lunch surrounded by the gardens and fields of Naumkeag. There is an admission fee which goes directly to maintaining the gardens.




After you get your fill of shopping and taking in beautiful gardens, our trip takes us back toward the Hudson Valley. Located on the border of Mass and NY is our next stop, Bash Bish Falls State Park. Located in Mount Washington, MA is the state's highest single-drop waterfall. The trails to the waterfall are very family friendly and meander along a brook fed by the falls. If it's a hot day there are plenty of places to take off your shoes and splash in the water, my daughter's most favorite thing to do on a hike. The whole hike in to the falls and out takes about 1 hour, round trip. There is free parking at the trail head and access to the park is also free.






There are lots of amazing, locally owned places to eat in the Berkshires; here are a few of our favorite family-friendly places:
  • Berkshire Mountain Bakery is hands down my most favorite place in Massachusetts. Located in Pittsfield just minutes from the museum. This locally owned cafe serves the most delicious homemade foods and the star of their menu is the house made bread, pizza dough and pastries. Take some bread home, it is amazing! 
  • Six Depot Roastery and Cafe is a small batch coffee roaster, cafe and art gallery in West Stockbridge, a short drive from Main Street and Naumkeag. Located in the oldest train station in the Berkshires, the space is very eclectic and has a great menu that will appeal to the whole family. I dare you to smell the coffee roasting and not leave with a bag of your own.
  • If you want to picnic in Stockbridge you have two options, the Elm Street Market will pack a picnic lunch for you or the Oak Cafe at Naumkeag also does the same. Both places offer simple sandwiches and salads to-go.  
Tips for this trip:
  • I planned this trip with driving in mind, I started in Pittsfield because it's the furthest away and the subsequent stops bring you back toward the Hudson Valley.
  • Bash Bish Falls is not stroller friendly so babywearing for new or non-walkers would be best.
  • Both the Berkshire Museum and Naumkeag are stroller friendly.
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