I hope early in Oct. A bit before peak is way better than a bit after peak.

FYI it's just past agricultural fair time.

It's over the border in VT. Go to Scott Orchards. They are serious about apples and have the most heirloom apples and it's super fun to go and get 20 kinds of apples you never had and taste test them. And it's pretty niche but if dry masonry and stone walls interest you... it's your place.

https://www.halloweennewengland.com/events/naumkeag-pumpkin-trail-stockbridge-ma

Have a picnic at the Mount. Edith Wharton's. It's free to use the grounds and the house costs money and is just meh-- as far as our amazing historic homes go.

Do Montague Book mill, drive to the top of Mt Sugarloaf for the view, and go to Northampton for people watching, food, Herrell's .