Going to a conference in Rhode Island in October
What else should we do while in the Northeast? Mind you I've never been north of Wash DC. We'll have a few days before/after and along the drive from Florida to see/do other things.
Boston, what's a quick must-see?
New York, what one thing should we see?
I-95 corridor?
Ah, a nice relaxing 12+ hour car trip with a 2 1/2 year old. Just call me Clark Griswald.
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Newport is a must. See how the top 1% of the 1% lived in the 1800s and the early half of the 20th century. Most of the homes are now historical sites, with the biggest and most famous being The Breakers, the home of the Vanderbilt family.
http://www.newportmansions.org/explore/the-breakers
If you want a quick outing, the Mohegan Sun and Foxwoods casinos are right over the border in Southeast CT.
You can probably find a New England foliage tour for October as well - some of the views will be stunning in October. You just have to plan out where it's best for the time of the conference. They have websites that have the location of the prime foliage time throughout the autumn - I think it moves South from northern New England to Southern through the season.
If you're in Providence for the conference, Boston is a lot closer than NYC (less than an hour vs 2 1/2 to 3 hours). There are a ton of things to do there, but I'll leave it to a Bostonian DUers to fill you in there.