Ok - officially old when we are planning a trip to see the leaves turn.
Suggestions - how soon start planning, where to start - Maine then NH, Vermont? Wineries, bed & breakfasts, what roads to take, hire driver?

We did this trip a few years ago and it's one of my favorite trips we've ever done! I didn't realize how beautiful New England is. We flew into Boston and spent a couple of nights there then drove to the White Mountains area of New Hampshire and rented an AirBNB in Bartlett, NH. There's tons of scenic drives and hikes in the White Mountains area and the fall colors are beyond spectacular. Don't miss the Mount Washington Cog Railway or The Bear Show at Clark's Trading Post.

Did this in 2019 with just my wife and it was incredible. We flew in to Boston and headed up the coast then into central Maine. Hiked Mt. Katahdin. Finished the trip in Bar Harbor/Acadia. Can't wait to do it again but kids are so busy now in the fall it's hard.

The go-to route to drive in NH is the Kancamagus Highway locally known as "The Kanc". It goes through the White Mountain National Forest from North Woodstock to Conway NH. There is actually a website dedicated to it that lists attractions, accommodations, best time to visit etc...

https://kancamagushighway.com/

Edit: Here is a pic taken on The Kanc on Oct 8, 2019 (for reference), and a pic of Nubble Lighthouse taken the day before.

Also did this same trip. Fly to Boston and rent car. 2 Days in Maine, 3 in NH and 3 in Vermont. Drive back to Boston and fly home.

Most people agree 2nd week on October is the best time for prime leaf viewing.

Great advice everyone. Are the roads crazy with traffic going on those curvy 2 lane roads? Best places to stop and eat or get a cocktail? Lodging suggestions?

When we were there in 2017 the crowds/traffic weren't bad at all.

Just remember when traveling in the mountains, a 30 mile trip is not 30 minutes like here in Texas, You have to double your driving times.

When doing my trip, we mostly stayed in Air BnBs. In New Hampshire, I would stay near or in Conway. It's a decent size town with all the amenities needed. The White Mountain NF is the biggest draw there.

malenurse said:

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Just remember when traveling in the mountains New England, a 30 mile trip is not 30 minutes like here in Texas, You have to double your driving times.

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In NH, if you want a little luxury on your trip, the Omni Mount Washington would be a good bet. It's right next to the cog railway and you should be able to get a highly discounted or free ride up the gondola at the ski area, which has awesome views. It's about half an hour or so from the Conway area.

Bumping to track responses, my wife and I are doing this same trip this fall!

Loved our trip to New Hampshire a few years ago. We flew into Manchester on Southwest and rented a car. Stayed in the Jackson/North Conway area.

Several people suggested the Cog Railroad to Mount Washington. We actually did the drive all the way up (and down). It was intense but a highlight of the trip. The winds at the top are no joke!

We also took the Conway scenic railroad one day and thoroughly enjoyed it - lots of gorgeous scenery but gave everyone a break from driving and more room to stretch out and walk around without stopping. https://www.conwayscenic.com/

We loved Peaches breakfast so much we went there almost every day: https://peachesnorthconway.com/
We also had a great time at the Shovel Handel Pub in Jackson for dinner and live music.