going out in western massachusetts
Western Massachusetts doesn't advertise itself very well. That's part of the appeal.
The 413 runs from the Connecticut River valley west to the New York state line — small cities, college towns, old mill buildings that became arts spaces, hills, farms, and an accumulation of creative people who ended up here and stayed. The Pioneer Valley has been doing this for decades. The Berkshires have their own version of it. Neither is the whole picture.
This is the guide. Both regions, by city or by what you're into.
pioneer valley
The river corridor from Holyoke north to Greenfield. Northampton is the anchor — music, drag, comedy, art, most of the major venues. Easthampton is doing something interesting on Cottage Street. Greenfield has Hawks & Reed. Florence has Bombyx. Amherst has The Drake and five colleges. Turners Falls has the Shea.
berkshire county
West of the valley, over the hills, down to the New York border. North Adams has MASS MoCA. Williamstown has the Theatre Festival and the Clark. Pittsfield is the county seat with year-round nightlife. Lenox has Tanglewood. Great Barrington has the Mahaiwe. Becket has Jacob's Pillow.