09/01/2026
September in Massachusetts is one of my favorite times of year. 🍎🍂
Summer isn’t quite over, but fall starts sneaking in — cider donuts, football Sundays, fairs, apple picking, and the first hints of foliage. And there is SO much happening this month.
I rounded up some of my favorite September happenings, restaurants worth trying, new spots to check out, weekend getaways, football-watching spots, and plenty of ideas to kick off your fall bucket list.
Basically, consider this your shortcut for the next time the group chat asks, “What should we do this weekend?” 👀
Save this one for later + send it to your favorite person to explore Massachusetts with.
🍁 Comment FALL and I’ll send you my full 2026 Massachusetts Fall Guide packed with even more local favorites, day trips, events, and things to do this season.
I’m Jackie Crawford-Ross 🏡 Massachusetts Realtor, a Massachusetts local and real estate agent sharing the best of life in Metrowest + Central MA (between school drop-offs, football/baseball fields, and helping people make moves 🏡). Follow along for more local recs!