UPDATE: Question about Connecticut towns

We used to live both near Hartford and near Norwalk. Take 1-84 from Hartford. The town of Southbury is charming , also Bethel, Redding, Easton, Ridgefield, New Canaan, Wilton. Westport on the water. That whole area ids filled with beautiful towns! I hope the leaves will be at their peak for your visit.

About 2 hours west, near Poughkeepsie, NY is the National Historic site of Hyde Park. The home, several buildings, locations connected with FDR and Eleanor.

In Hartford, I enjoyed touring Mark Twain home.

I know going north isn't the best,but want to mention about an hour and half north is Stockbridge which has the Norman Rockwell museum and Stockbridge is featured in his paintings. Here is info on other things in the area. https://www.travelawaits.com/2556800/best-things-to-do-in-stockbridge-ma/

On the way there you could stop in Great Barrington at Guthrie Center if you are a fan of the Alice's Restaurant saga :). The Guthrie Center is in the church featured in the song. (Alice's Restaurant location is in Stockbridge.) Apologies to those who have no idea what I'm mentioning. It has been about 8 years since I've been in the area so check to see current visitor information.

It is not CT but about hour and half east to Newport RI and those magnificent mansions. Then I seem to remember it is about two hours south to Norwalk. whatever you decide you won't be disappointed.

In my opinion, the western side of the state is the most scenic, particularly in the Fall. You could drive west from Hartford to Litchfield, which is pretty much a quintessential New England town. It has a small main street with several shops, restaurants and coffee shops. It is known for its elegant and historic homes. If you follow Rt 202 out of Litchfield, you will pass several nature preserves and state parks, which have nice walking trails. About 15 minutes or so from Litchfield, you can take Rt 47 into Washington, CT which is smaller than Litchfield but is once again quintessentially New England (White churches on the green, old clapboard homes, old stone walls, farms, etc). Steep Rock Preserve in Washington offers lovely walks along the river. Lake Waramaug is just north of Washington in New Preston and a drive around this lake offers some of the prettiest foliage sights. Additionally (or alternatively), you could drive up Rt 7 to Kent which is also a small, pretty town. Further up Rt 7 is Cornwall Bridge, which as the name suggests, is home to a scenic covered bridge. The foliage there is also usually quite beautiful, as Rt 7 at that point runs along the Housatonic River.

So far, the trees are still pretty green so fingers crossed that the 15th will be peak.
Personally I wouldn't bother going as far as Hyde Park, although obviously, it depends upon your interests. It would be a longer drive than you are looking for and the area lacks the charm of the New England towns I mentioned. Southbury really doesn't offer much in the way of charm. Years ago, it may have. But its Main St. is now just one small strip mall after another.

Thank you all so much! These are great ideas and really really help with our planning.

Suki, thanks for the ideas! Some of those are close to Norwalk and we could even try to hit some while we're staying there.

Lynn, I am a huge Alice's Restaurant fan (and Arlo Guthrie) and would love to visit there (and Stockbridge). But I think it will have to wait. I'm actually planning a 3-4 week road trip next year from Minnesota up through Canada to PEI, then down through New England and will definitely put those on my list.

mmk, those sound wonderful! I sent this to my sister and she was very excited - this has been on her bucket list for awhile. She has voted for staying in Litchfield and then exploring from there. Thanks!

All great suggestions posted above , I am very fond of the RT 7 corridor in Western CT up into Massachusetts , and visit the area frequently . Not meaning to throw a monkey wrench into this , but keep your expectations about leaf peeping within reason . We had a very hot , and extremely dry summer in New England this past summer ( we live in Westchester County NY , three miles from the CT border ) and the level of rain was - none . That affects the color and intensity of the display . Several years ago , on a trip trough Western CT and The Berkshires to Vermont , there was little color due to the lack of rain that year . Enjoy your time there , in any event , the area is absolutely beautiful .

I agree with Steven. Rather than take the interstate south, head over to Rt. 7. Much prettier.

Steven, I was wondering about that and will not get my hopes up. I think my sister will enjoy seeing some of the quaintness of New England even if we don't get the full color blast. Rt. 7 looks like a nice drive so we'll definitely try that.

Frank II, thanks for your thoughts - the nice thing is that whatever we don't see at the beginning we can visit after the wedding is over.

As Frank said , don't head for the Interstate ( I-95 ) , it's a traffic choked mess with nothing to see. Route 7 runs right up from Long Island Sound through Norwalk . A little more than an hour will put you in Kent , CT , and not far from there, perhaps fifteen or twenty minutes , Kent Falls State Park , and the West Cornwall covered bridge .

Update: We made it here and the foliage is beautiful! My sister just loved it! We stayed in Litchfield the first night, which was charming and enjoyed some leisurely driving down Rt. 7 the next day. Beautiful fall colors! The colors disappeared somewhat as we got closer to Norwalk for the wedding, but after the wedding, we headed back north to Hartford and wound up staying in Glastonbury, which we loved. The oranges and yellow and red colors in the trees were absolutely radiant. We also spent time exploring the many historic houses in Glastonbury (including one from the 1600's). The town is really nice (in fact, I told my sister that I could easily live here). :)

Glad to read your post ! It's beautiful there , even in the dead of Winter , when a quiet stillness settles over the landscape . How much longer are you staying in the area ? Writing from Salzburg now .

steven, lucky you in Salzburg (speaking of beautiful landscapes)! Sadly, we were only there from Thursday through Monday, and most of that was spent at my cousin's wedding in New Canaan. But I am going back next fall and will spend much more time there!