New England foliage trip

This isn't foliage, but check out Marblehead. It's right next to Salem and has a very picturesque harbor and old fort. Across the harbor is a nice lighthouse. I used to photograph this spot all the time. Beautiful historic houses all throughout the town.

Okay! I'll check that out
Thank you!

Sorry to throw a monkey wrench into your plans , but that's alot of driving for two days , and very little return for all that time behind the wheel . The quantity of places to see and stops to make in New England is endless , so here is what I suggest to get more bang for your buck . Salem is worth some time , but be aware that it's clogged with phony witch oriented junk . A walk through sections of the old town , and the Colonial Era , McIntire designed architecture , will serve you better . The National Park Maritime site at the harbor is also time well spent . As has been said, Marblehead is a winner and isn't far from Salem . After that , a relatively short amount of driving will send you from Salem up RT 127 to Cape Ann and then along the North Shore up to Newburyport . This area comprises a 25,000 acre salt marsh and villages of charming nature ,like Essex , Rockport , Ipswich and others . This also keeps you within about a 40 mile distance of Boston . New Hampshire and Vermont are absolutely worth a trip , but two days is really pushing things .

@Steven I should have added that we don't mind a decent drive. We are currently renovating a second home and the drive is 2 hrs and 40 each way. We frequently go on Friday night to return late Saturday or early Sunday of the same weekend. I've also driven across the mountains to Gatlinburg to visit my sister for a day or two each year (that is a 7 hr drive). So the drive probably won't bother us too much, but I do take your advice into consideration!!

Also, we will have 4 full days - Wed-Sat. We fly back early Sunday. I just don't know what to do with all those days as normal we country hop when we travel lol it isn't uncommon for us to visit several countries within a few days when in Europe. We don't like to stay in the same place for too long.

Which is what I was thinking with Salem. I figured what you said about it being cheap, unauthentic "witch" overload. Which is not historically accurate, just a tourist gimmick, since those in the trials weren't really witches. I will definitely look into those places you've mentioned! Thank you!

Foliage timing is unpredictable, so planning a route that covers as much north/south distance is always advised. The wet summer would normally indicate a later peak, but we're already seeing some color here in the foothills to the Berkshires, which seems early.

Edit to add- Maybe look at flying home from Hartford to prevent backtracking into Boston.

Ordinarily, I would agree with Steven. However, if foliage is what you want to see, I wouldn't stay on the coast. It is hard to tell when the leaves will change anymore, but it used to be 10-13 days into October was a safe bet. Last year...I thought the foliage leaned towards brown, but there was a drought. Drought is no longer. You can usually check foliage forecasts in late September to know if NH or VT, north or south, would be best. Not knowing at this time, I suggest the following.

In October, the prime areas of Salem are beyond crazy. I suggest getting in and out, ASAP. Just see the memorial and leave. If you have an interest in Concord history, Battle Ground Park, etc. Stop around there for your first night. However, it's only about an hour from Salem. As you are not dealing with a time change, you might want to head further up Route 93 at a nothing stop. Then the Kangamangus Highway is lovely and could be done on your way to Franconia, round about. I also love Franconia and used to have a ski place there, so I'm partial. In Franconia, you could ride the ski lifts up to the top of Cannon Mountain for a view and/or head up to Brettonwoods and have lunch at the Washington Inn...make sure it is open. And/or head over to VT. As Stowe is so aligned with skiing, I don't go there. It's fake. LOL. As you love to drive and don't sound like you want to go to shop, etc. I'd suggest going up to Waitsfield, VT where the Appalachian Gap is. There is a beautiful view there, obviously. And, at Mad River Glen, you can also ride the ski lifts, if open, up to see the foliage. Check the timing of the App Gap bike race, because you'd have to put a hold on your trip up there just until it is finished, but the ski lifts would be open. If going to Waitsfield, I would drop Brettonwoods, but that's just me. Then on day three make your way back to Boston. However, that extra day does afford you a change of plans if you decide day two's drive is too much, which will be all day, but that seems what you want. I have done Waitsfield, VT through Warren, NH to 93 and back to south of Boston in a day, with several stops along the way and it was fine so you could do even more, IMO. I don't know how the cross over would be during foliage season so that is not necessarily your route. There was no cell service during part of that route. I was stopping to visit ancestors from Warren, NH, which was the reason for that route. Sounds like a fun trip.

Thank you, @scudder - I will definitely keep that in mind!

Oh my heavens @wray - you get me! That was a BEAUTIFUL reply and exactly the kind of information I like to hear! And you are correct - I do not care for shopping and would much rather see nature views.

100% I will take all this information into consideration while planning!!! Wonderful, wonderful input from everyone! As always, you all are amazing on here!

Wray gave you some great suggestions -- I second the recommendation for the Kankamagus and the Waitsfield/Warren area. If you do the loop she suggests and head from Franconia towards Vermont, you can take Route 302 across the northerly part of the state, which is is a lovely drive. Then head over to Route 100 and head south on your way back to Boston. Again, another lovely drive on 2-lane, windy roads (though 100 can get traffick-y during foliage season). As much as you can, if you have time, take the back roads -- much nicer driving, and you'll pass through all the pretty villages along the way.

I hope the leaves hold on this year -- we have had SO much rain. Many of my sugar maples have leaves turning brown and dropping :-(

I am in northern Vermont at a pretty high elevation, and peak foliage for us is usually that first week of October. Southern areas and valleys will generally peak the second and third weeks of October. But it's very weather-dependent and varies year-to-year. So make sure you plan for a range of travel so you can hit peak season somewhere.

Enjoy your trip!

Here is something I posted last year when I went to New England and wanted advice about foliage. It's a bit farther than you are looking for but just in case, you might get some ideas. :) https://community.ricksteves.com/travel-forum/beyond-europe/question-about-connecticut-towns

Get your hotel reservations asap!

Just wanted to check back in and thank everyone for the suggestions and update on our route.

We arrived in Boston Wednesday morning around 10:30. Left the airport with our rental car around 11:30 and drove into Salem. I visited an ancestors memorial (Twenty Benches) and then we headed to Danvers to another memorial with her name listed.

From there we went to York Maine and had some seafood and then made our way up to Alton NH where we had booked an incredible Airbnb. Thursday morning we to Concord to hit the Kangamungus Highway and did some stops for hiking and views along the way. Walked the Gorge in Lincoln then decided to see what all the fuss was about with Artist Bluff.

Friday morning we got up and tried the popular Pollys Pancakes. (It was okay. But nothing worth the hype or hour wait) Then we drove to Chelsea VT to take Highway 110 down to Woodstock. We meant to see the covered bridges but our son was sleeping so well in the car and we ended up missing all but one. Still a nice country drive though.

Stopped at Sugarbush Farm for some amazing cheddar cheese and maple syrup before going to Concord for the night. Saturday we headed to Boston and did the Freedom Trail before getting up at 3 am to catch our 6 am flight home.

This was the perfect itinerary for us with our 15 month old and we had an awesome time! But the Freedom Trail was probably my favorite part...even with the rain!

Thank you all for your input and suggestions!!!