We are planning to drive from Glen Spey New York to Boston, stay in Boston for a couple days; then drive from Boston to JFK airport. We'll be starting in Glen Spey on Oct 22 morning, and ending in JFK on Oct 25, catching the flight at 6 p.m. ( total 4 days and 3 nights ). We would like suggestions on choosing which scenic routes, what to see/to do, plus what town/city to stay overnight between Boston and JFK. Is New London a good place to stay one night, or other choices.....BTW, we are from Los Angeles....Thank you !
Connecticut is a beautiful, often overlooked state when it comes to visiting New England. Check out the CT website: 52 Getaways. I highly recommend Mystic for your overnight and I actually stayed at the Mystic Marriott for a wedding in October of last year. A wonderful time of year to explore the old port.http://www.mysticseaport.org/. Then, if the traffic is right, you should take the Merritt (CT-15) through CT instead of 1-95 on your way to JFK. It will be gorgeous that time of year.
That time of year you could also catch a night at the Mystic (a great place for sure) then hop on the ferry over to Long Island from New London CT. That will take you to Orient Point NY (right where I used to live) and then you can enjoy a very scenic drive through the east end of LI. There's 50-60 wineries if you are into those things or you could take in the town of Greenport, hop the ferry across to Shelter Island, sight see then hop the south ferry over to Sag Harbor/Hamptons areas. Lots of things to see/do until you get to Riverhead, at which point you are best hopping on the LIE or southern state and heading to JFK. The ferry isnt cheap but probably works out pretty close time wise and tolls you spend to come down the mainland and across to JFK.
There's also some pretty amazing B&B spots out east, some great restaurants and plenty of "old town USA" you can drive through on the way out. Let me know if you need any help if you choose this route, liwines dot com is a good resource for wineries.