Boston: stroll along Charles St for some cute shops, and Beacon Hill for historic homes, and the Public Garden, all near each other. From there, you could continue to Newbury Street. Then continue to the South End, lots of restaurant options around there. All walkable, depending on your energy level and ability.

I went to this inn in VT two years ago with friends, around this time of year. We loved it.

https://www.hillfarminn.com It is about 3 hours from Boston.

There are a lot of pretty towns along Rte 2 heading west. Concord, Stow, Harvard. That’s where we all go apple picking in the fall! You could take Rte 2, then 91 north into VT.

Salem, Ma. Is lovely in October. Food was wondeful and lots of history and house tours too. I stayed at the Merchant, but there were loads of great hotels downtown to choose from.

https://www.google.com/search?q=the+merchant+salem+ma&ie=UTF-8&oe=UTF-8&hl=en-us&client=safari#ebo=0

Adding to Boston suggestions: see the glass flower exhibit at the Harvard Museum of Natural History. Also the isabelle Stewart Gardner museum.

There is an historic home tour in the South End Oct 17 that I will be at. : )

I adore the Mayflower Inn and Spa. Planning to head back again next year. Theoretically the wrong direction but I don't actually think so.

Also Porches and Mass Moca.

Maybe do both in a circle from Boston.

Oh and Woodstock VT

I would love to visit Salem again but it is absolutely nuts in October from videos I"ve seen online.

(Mtn: Isabella Stewart Gardner Museum.)

I love Woodstock VT too. Oh and King Arthur Flour is nearby and offers classes.

I am actually going to Salem tomorrow. I’d stay away in mid Oct, though.

I went with kids so the Halloween of it all was brilliant lol.

Love all your thoughts and ideas. Thank you SO much!

If it's foliage you want, you'll have to get out of Boston to see it.

There is a fantastic interactive map that can help you plan your trip around the foliage. We've used it for years and I think it is fairly accurate..

https://www.explorefall.com/fall-foliage-map

There will only be moderate color in Boston if you go during the dates you posted. Your best bet would be to start in the North (say Vermont) and then drive south. To avoid driving and parking in Boston you can catch the hop on - hop off bus that takes you to many of the best sites.

Hmm... if you are really into seeing the foliage, and those are your dates, maybe start in Montreal...

I think there was a similar post to this one where I mentioned NH. Did you see that?

Somehow the thread on kitchen table reappeared so here's my comment. Maybe it will be helpful in the future:

I'd head to NH. The view from the back deck of the Mt Washington Resort is unparalleled. Whether you stay there or not, have a cup of tea there to enjoy the view. Take the cog train up to the top of the mountain. Take a boat ride on Lake Winnepesaukee. Head to Franconia Notch. See the waterfalls at Diana's Bath. If outlet shopping is your thing, you can do that in N. Conway too...esp if it's a rainy day. We stayed at Stonehurst Manor which includes breakfast and dinner. Mind you this was many years ago so things may have changed. But it's some thoughts about what we enjoyed when we were there.