New England Leaf Peeping: October 2024 Itinerary

The six states of New England provide some of the most outstanding leaf peeping opportunities out there and we’re planning to go this fall to see what all the fuss about.

Golden fallen autumn leaf peeping graphic.

If you’re unfamiliar with the term leaf peeping, it’s the act of intentionally admiring spectacular fall foliage. Here’s a link to finding your best fall foliage this year.

Overview of Our New England Leaf Peeking Plan

Orange fallen autumn leaf peeping graphic.

New England, in the most northeasterly section of the United States, is made up of six states. Connecticut. New Hampshire. Maine. Massachusetts. Rhode Island. Vermont.

The 7-day planes, trains and automobile trip I am planning for me and my husband will take us through all six.

Hand-drawn map of the 6 New England states and New York, superimposed with a color coded fall foliage tour route.

Google map attached below.

Day by Day

Green fallen autumn leaf peeping graphic.

It can be tricky planning multiple day trips. Especially in unfamiliar places. Most importantly, in a way that everyone in your party enjoys themselves, learns something new and/or doesn’t get sick or injured.

I like to start by gathering my traveling companions’ to-do lists so I can integrate something for everyone into the plan.

My husband is easygoing and I have a pretty good idea of the sights he’ll like and those that’ll make him grumble. So this part is simple for my trip.

Feel free to tweak this plan to suite your needs or if you find anything to your disliking.


Hand illustrated yellow Lone Star with a swish on either side.

Historically, the window for viewing peak displays of fall color in New England is mid-September to late October.

Keeping in mind, peaks sweep north to south, as the season changes. So areas in northern Maine, New Hampshire and Vermont will show off their best stuff well before the leaves change in southern Rhode Island and Connecticut.

From what I’m reading, the best views last a couple of weeks, with the very best time being in the middle of those weeks. The kicker, of course, is there’s no pinning down Mother Nature. Therefore, if you’re planning months ahead, like I am, you kinda have to go with the historical dates.

Since we’ll be traveling west to east, from Saratoga Springs, New York to Portland, Maine, our best time for New England leaf peeping will be early October, preferably the first week.


Since I’m still early in the planning process, and have three months to work on this, there is vagueness galore in this “plan”. Once details start clicking into place, I’ll update this post.

Google map of New England Leaf Peeping route through New York, Vermont, New Hampshire, Maine, Massachusetts, Rhode Island and Connecticut.

Day One ~ haven’t chosen dates yet, but that would go here ~ Fly North like a Loon

Fly into New York City from San Antonio. Non-stop, 3hr32m flight.

Yes, there are other airports on either end of this journey. For more info on booking flights, click here.

Land about noon (11:00am our time). Make our way to my sister-in-law’s in Brooklyn. Will need her to map that out.

I’ve walked across the Brooklyn Bridge before; my husband hasn’t. So that could be fun.

Day Two ~ Start Spreading the News

Sightsee in Brooklyn and maybe New York City.

Eat in Little Italy. I did this on a previous trip. Even though the waitress insisted I say manicotti over and over again, until I got it right, I’d love to go back!

Day Three ~ Hitting the Rails

Red fallen autumn leaf peeping graphic.

Catch the Adirondack Amtrak train line at Moynihan Train Hall in Penn Station. Departs at 8:35am (yipes). Will keep reminding ourselves that by leaving so stinkin’ early, we’ll have the entire afternoon on the other end.

The Adirondack line travels north along the Hudson River, through New York’s wine country. The line ends in Montreal, Canada. We’ll be disembarking in Saratoga Springs, New York at 12:28pm (if the train is running on time). Estimated 3hr53m trip.

Pick up rent car. Eat lunch, look around Saratoga Springs.

Staying in New York, drive east to Salem, Granville, Middle Granville, then up to Whitehall. All of these towns have points of genealogical interest, so we’ll see those. About 60miles, 1hr26m drive.

Drive barely into Vermont (13 minutes), stay in Fair Haven.

Day Four ~ Leaf Peeping across Three New England States

Breakfast on local foods, maybe a bed & breakfast?

Orange fallen autumn leaf peeping graphic.

Drive 20 minutes to Rutland, Vermont for one more genealogy stop. Start scenic byway Crossroad of Vermont, Route 4. It meanders through the Green Mountain National Forest. Stop for a gondola ride at Killington Resort. Tickets are for one-way or roundtrip, hmmm. There are times I might hike down a mountain, but this one would take me several days, so no. Lunch at the Peak Lodge?

Side note! I ordered the tourist packet from the Vermont Tourism, with maps and such. Maybe I’ll do an unboxing video when it arrives!

Drive to Hartford. There are 3 covered bridges along Route 4 between the resort and Hartford. That’s cool. 25 minute drive from Killington Resort, 38miles. Turn north on I-91 to Bradford and then wiggle up the VT/NH border on US-5. Turn onto NH-116 to NH-112 to Lincoln, New Hampshire, 1hr20m drive. I sure hope there is a state line sign to take a picture with.

Lincoln is the start of the 34.5 mile Kancamagus Scenic Byway, heading east. The route transverses the White Mountain National Forest. Might be nice to stop at the Rocky Gorge Scenic Area.

Sunset expected at 6:23pm.

Drive 1hr30m to Portland ME.

Stay there. Return rent car. Eat lobster.

Brown fallen autumn leaf peeping graphic.

Day Five ~ And I’ve never been to Bwaston in the Fawl

That quote is from VeggieTales. It was one of my kids favorites when they were little 😘

Breakfast in Portland, somewhere with more New England leaf peeping.

Look around town until Amtrak Downeaster leaves for Boston at 1:43pm. Arrive at 5:05pm. Check into the hotel. Find something fun to do. Stay in Boston (probably our priciest night of the trip).

Day Six ~ Zip through Two of the Smallest States

Breakfast in Boston. Tea party perhaps?

Green fallen autumn leaf peeping graphic.

All aboard the Northeast Regional Amtrak train at 11:46am. Arrive in Providence, Rhode Island just after noon. Find lunch somewhere fun before climbing back aboard the Northeast Regional for New Haven, Connecticut at 2:36pm for a 2-hour ride along the Long Island Sound.

Stay in New Haven.

Day Seven ~ Head North to go South

Hop the Hartford Line in time to catch our Delta flight home, via Detroit.

Home by midnight, hopefully.

I hope you picked up a few ideas for your own New England leaf peeping trip!


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