If you’re looking for a very underrated area that still has quite a bit going for it (even during the winter), I’d recommend checking out the Greenfield area.

Greenfield itself is a pretty small city, downtown has some nice shops and restaurants. By far the coolest thing there is Poet’s Seat Tower, a brick tower that overlooks the entire city and gives you some stellar views of the mountains and surrounding landscape. You can hike or drive up to it.

There are a bunch of small towns that surround this area, my favorite being Shelburne Falls (part of Shelburne and Buckland). This has the Bridge of Flowers (a pedestrian bridge covered in flowers and plants), the glacial potholes formed during the Ice Age, and a quaint little downtown area.

When you drive in from Eastern Mass, you’ll go across the French King Bridge which connects Gill and Erving…an absolutely stunning natural vista over the Connecticut River. I’d also recommend checking out Turners Falls briefly for some more scenic waterfall views. It’s a bit run-down, but I like the falls.

If you’re looking for something indoors, the Yankee Candle Co. Flagship Store in Deerfield is genuinely a really fun and interesting store to walk around and explore…it’s not just candles. There’s a section of the store that “snows” every couple minutes.

I have fond memories in this area as a kid so I’d definitely recommend checking it out if you haven’t. There’s a lot more I’m leaving out, mostly outdoor hiking and stuff. I’d even say just take the whole Mohawk Trail down to North Adams if you want a full experience, lots to do down there too.