Trip to New England end of October
 

We're trying to plan a long (adults only) weekend trip for our 10th anniversary, looking forward to some crisp air, beautiful historical locations, fall events, art, local culture, great food, beautiful fall atmosphere... mostly just some time alone to enjoy a new area.

We've been considering a few destinations -
Portland, ME (the "Grand Tasting on the Harbor" is that weekend, which looks really interesting)
Providence, RI
Boston/Salem
Newport

Having never been to any of these places, thought we'd look for some advice/suggestions as to what might be ideal considering our timing (the last weekend of October - 24th - 27th). We live in FL now, so fall foliage is a draw but I realize we'll be going up a little late & will probably miss the peak times.

Thanks in advance for any input on these or any other suggested destinations.

You will definitely miss peak foliage time and judging from the already unseasonably cold nights we have had I think the trees will be all bare.
I am not sure why Providence?

Skip Salem any time near Halloween.

It might sound like fun but it isn't.

Thanks for the responses. Providence was suggested by a friend, thought it was similar to Newport, charming historical old city with lots of local culture and art. I think Water Fire was also mentioned as an interesting river event during the time frame of our travel.

Thanks for the advice to skip Salem, it sounded like an interesting place to visit but you're right, we'd prefer a time when it's not overwhelmed with tourists. Wasn't thinking in terms of Halloween. :o)

Don't know your budget but you might consider one or all of the following:
Otesaga-Coperstown, NY
Castle Hill-Newport, RI
Ocean House-Watch Hill, RI
Wentworth by the Sea-New Castle, NH
The Boulders-New Preston, CT
Madison Beach Hotel-Madison,CT
Weekapaug Inn-Westerley, RI
Mayflower Inn-Washington, CT
Also, in "lower" New England on Oct. 24-27 you still have a good chance of seeing colorful foliage.

You might luck out on some color if you do a RI visit. We were there Oct 23 one year and there was still some color left. We looked into the food tour of Federal Hill in Providence for this Sept but the date we wanted was already sold out. We have enjoyed food tours in Boston, NYC and Portland ME but you could easily design your own tour in Portland (someone one chowhound is doing that). It didn't have quite the historical info the others did.

Providence will be mobbed for Waterfire. It's ok if you like crowds and music. All restaurants in the area are mobbed then and the nearby mall area is lined with places like Spaghetti Factory. If you do Providence, I would have a reservation someplace.

The Native American museum at Foxwoods in CT is outstanding. This would be worth the drive. It's not at the casino. We visited on our way back from Mystic but it shouldn't be too far from RI (googlemaps says one hour from Providence).

Since we could have some miserable rainy weather, I would opt for a destination that has some good indoor activities like a museum.

It was years ago that we enjoyed a tour of the Johnson and Wales culinary museum. I think it may have been moved and updated. You need a reservation to have a tour guide.

If the weather is good, I'd opt for Portland ME and a morning trip on the mailboat. There is a little narration and it's interesting since this is a working boat and people working on the islands commute via mailboat. You will probably need hats and warm jackets.

So far not mentioned...areas in or around Boston such as Nantucket, Vineyard, Gloucester, or perhaps Concord-Lexington.

If you want crisp air, go north. You will miss foliage most likely, no way to know until it happens. I would suggest the Berkshires. It has great art Clark Museum, Norman Rockwell, MassMoca and one at Williams College, real New England town feel, outdoor activities, small mountain for hiking, biking trails, cozy inns, great food. The tourist season is over so the big concert events, Tanglewood, are over too, but if you want the place to yourself, it is where to go and there is plenty to do. The only down side is driving out there, but you can make that an adventure itself as there are plenty of interesting places to stop along the way.