Scenic drive from Newport, RI to the Berkshires
 

Hello there! This weekend we'll be taking a drive from CT to Newport to Berkshire County to enjoy the foliage. Could anyone suggest the best scenic way? We don't mind if takes longer, we just want to enjoy the views and quaint towns on the way.
Any suggestions of quaint towns and restaurants on the way that we shouldn't miss is appreciated !
Thank you so much!

Is this a round trip or are you going returning to Newport?

I am willing to invest some time in this -- it is a beautiful trip -- but the routing would be different depending on what you plan.

Thank you so much Ackislander for your help! It's a round trip from/to JFK airport.
Friday morning driving from JFK to New London, CT then Newport RI then drive up Saturday morning to Berkshire County. Not familiar at all with the area. We love road trips. Would love to see some beautiful foliage and quaint towns on the way.
If you have any suggestions for CT as well, if you know any quaint towns I should stop by on the way to New London and Newport please let me know.
Planning to spend 2 nights in the Berkshires( Lenox maybe?) driving around ( I was advised the Berkshires should have great foliage) then Monday morning start driving back to JFK, afternoon flight.
I appreciate any suggestions !

???

Berkshire foliage is still lovely, lovely to the point that reservations for the weekend might be tough.
Be sure to drive to the top of Mt greylock if you get a clear day, you can see really far.
I love the drive along rt 2 this time of year. Right off two about 15 minutes west of greenfield is lovely Shelburne falls , still with the feel of an old New England town and with gorgeous glacial potholes.
You might like to stay in Great Barrington as opposed to Lenox as it is less formal and quirkier.

You will need to get moving very early the day of your flight.

That is a very, very fast trip.

I don't know where you live, but it will take about twice as long to get anywhere after Newport

From JFK to Newport is about 5 hours with no stops mostly by I-95. So you get there mid-late afternoon if you don't stop in New London, walk around, have dinner, then drive to the Berkshires next day.

I would use your favorite map program to go from Newport to Pomfret, CT. Go west from Pomfret on US 6 to I-84, then north on I-84 to Sturbridge. Take US 20 from Sturbridge to Stockbridge. US 20 passes through a lot of nice country but it is easy to bail out to the MassPike if you need to make time for a while.

In your two days in the Berkshires, you will want to see Stockbridge, West Stockbridge, Lenox and Great Barrington in MA, and swing down into Connecticut, at least to Canaan and perhaps further south into Litchfield County.

To return to JFK, cross over into New York State and take the Taconic Parkway to NYC. No trucks and very scenic.

I agree with jubilada that Rte 2 west in MA is a beautiful drive. (This route is called the Mohawk trail) If you want a nice drive with foliage I would really recommend going farther north than CT at this time. See your other thread for other specific suggestions

The foliage in CT is fantastic today. We flew in on Tuesday and looking down at landing was a visual treat. The maples and birches are yellow, orange and red while the oaks are still green, so there is not the grey of bare trees yet.

Your trip should have some wonderful views, do pack or buy some warm clothes as there is really cold weather predicted for this weekend, evening lows near/below 32F (0C).

Wonderful! Thank you Ackislander for your detailed directions I love it!
Warm regards from sunny South Florida.

Still looking for that "hole in the wall " kind of restaurant experience in Newport, and the Berkshires, not fancy just great food! Thanks

I hope you are not planning on staying in New London. There is nothing charming about this city. So, what is your plan there?
Also, is there some reason specific you are going to Newport?

My favorite not fancy but really great food is at Elizabeth's in Pittsfield, off the beaten track. You need a reservation.

Hole in the Wall, Newport area: Anthony's Seafood, Aquidneck Ave, Middletown. Fish store and cafe combined.

Paul, No advertising on Fodors.