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My Strange Family spent last weekend in the Berkshires, Massachusetts. It was our first time exploring that region, and it is amazing the contrast of NYC to the hills and open spaces, in a short 2 hour drive. The main reason for the trip was to attended an Outstanding in the Field dinner (I will write about this in another post), but we turned the trip into a mini family vacation.

The Berkshires

Where we Stayed
My husband spent a few days looking for a house to rent, but most owners wanted a weeklong commitment so we ended up staying at the Holiday Inn Great Barrington. The hotel was no thrills but perfect for what we needed, they had a suite to easily accommodate our small family, breakfast included, a crib, plus an indoor pool (H loved that).

Where we Ate
As a family we ate at three restaurants and two ice cream shops in Great Barrington.
Baba Louie’s– Casual family dinning with tons of different wood fired pizza choices and a kids size pasta. The wait was short the food came fast and everyone left full and happy for about $12 per person.
Martin’sBreakfast served all day long. Martin’s makes all of the basics, but they make them good. H had the Mickey Mouse waffle and shrieked with joy when it came to the table. We had no wait at all (probably because we were there after Labour Day) and had great service. We paid $10 per person including coffees and fresh squeezed orange juice.

Martin's Great Barrington

Martin’s, Mickey Mouse Waffle

Gypsy Joynt– Upon entering the Gypsy Joynt it looks like a bohemian bar from the 60’s, but they have highchairs so I knew as a family we were welcomed. It is not full service so you order your food at the counter, then they bring it to your table. The focaccia bread burger was delicious, H had a chicken quesadilla and I took home a huge ooey gooey cinnamon roll for the car ride.

Gypsy Joynt

Gypsy Joynt, Great Barrington

FroyoWorldThis place is great because you pay for your yogurt by its weight. It is completely self service, with 10 or so flavors and as many topping choices as you could dream of. Just make sure your eyes are not bigger than your stomach or you will be paying for it in the weight.
SoCo CreameryLets just say you cant miss this ice cream place when you are in Great Barrington! The ice cream was creamy, fun flavors and fresh.

SoCo Creamery Great Barrington

SoCo Creamery, Great Barrington

Where H Played
With a 2.5 year old our lives revolve around parks. So, after searching for a park for H to play at in Great Barrington unsuccessfully, we ended up going one town north to Stockbridge. The playground in Stockbridge had a merry-go-round, pony on a spring, climbing bars, swings and a huge climbing fort with a slide. The park was nicely shaded and kept H entertained for over an hour.

Stockbridge Playground Berkshires

Stockbridge Playground, Berkshires

We enjoyed our short mini vacation in the Berkshires and would love to go back again for a longer stay in the future.

What is your favorite place to take your family within a few hours drive from New York City?