It's a bit too early to find anything in the way of fall color in and around Boston right now. Your best bet would be to head over to Vermont and then maybe move south into western Massachusetts and the Berkshires as the days go by.
Due to the prolonged drought throughout New England, they were predicting that the colors would peak sooner and fade more rapidly, but I don't know if that has actually been the case.
Be prepared for overcast skies and occasional rain for a good portion of your trip.
Here is this week's report from the Vermont Tourism office.
WEEK 5, OCTOBER 6, 2025
Most areas of the state are at peak foliage, or slightly past at this point. There are still lots of reds, oranges, and yellows throughout the hills, but some trees are beginning the annual ritual of dropping their leaves. The falling of leaves from our hardwood species can create another scenic autumnal experience as the slowly descending foliage sweeps across roads and trails. The crunch of leaves underfoot makes a great soundtrack for fall adventure while out and about, looking to the hills and surrounding forests for the fall hues that are still hanging on coloring trees. As foliage drops off trees, views from peaks open up for those hiking, driving, or taking a scenic foliage chairlift ride to the top.
Best bets: Southern Vermont has the most leaf retention currently, with areas around Bennington and Brattleboro still putting on a great show. More northern areas have begun to drop their leaves, but there are still many portions of the state where vistas of hillsides are yielding good color, even in northern reaches. VT Route 12A is a particularly nice drive right now between Northfield and Randolph.
Best of luck,
Merrill