Great Barrington, MA - Great Barrington is ten minutes from where I grew up and one of my favorite places. A great get-away from New York City filled with local restaurants, (Baba Louie's Pizza is my favorite), clothing stores, and a hole-in-the wall burrito place I've gone to since I was young. Railroad Street is charming, and Bizen is a delicious GB institution. Great Barrington is about a 35 drive from Salisbury, CT.

Mass MoCa, North Adams MA- I haven't actually been here, but people seem to love it!Described as "evocative art" and known for their large-scale immersive art installations, this is a fun spot to stop by, but a bit of a drive .

Tanglewood Music Center - In addition to having my high school graduation here, Tanglewood is a great spot to have a picnic on the lawn while listening to The Boston Symphany Orchestra, jazz, and if it's a lucky weekend, James Taylor. Bradley Cooper also shot his latest bio-pic here last summer.

Monument Mountain - This is a nice hike that I've done a handful of times. It has a great view, close to Great Barrington and across the street from where I went to high school.

Lakeville Lake - This is a quintessential New England vibe with sailboats, kayaking, and swimming. A great place to bring kids, relax, and cool off.