Spectacular New England Fall Road Trip
For years, I have been dreaming of a road-trip around New England. Since spending basically my whole life in Texas, where you can drive for 10 hours and still be in Texas, I have always been fascinated by the idea of crossing multiple state lines after only a couple hour’s drive.
Everyone knows New England to be one of the best places in the US for leaf peeping and all things fall. So what better way to enjoy New England than a fall foliage road trip?
This guide will provide you with tips and suggestions for planning your New England fall foliage road-trip as well as recommendations for things to do and see in Vermont, Massachusetts, and Connecticut. Had time allowed, we would have also added New Hampshire and Maine to our itinerary. If you have room in your schedule, I would recommend adding these to your list as well.
Pre-Trip Planning & Tips
When Should You Go?
Typically, the best time to see color is late-September to early-November depending on how far north you go. Keep in mind that the color change happens at a different time each year depending on the weather.
We visited the middle of October and it worked well for us.
New England Fall Road Trip Tip #1 – Be Flexible
Typically, I’m one of those travelers who meticulously plans out every hour of our trip so not one minute is wasted. However, trips based on seeing fall colors actually works best the other way – not planning a thing. You see, the color change can be unpredictable. Usually, the colors change from north to south, but it isn’t always an exact science. My husband and I were a bit disappointed when we first arrived in Vermont because a lot of the trees already looked bare but as we kept driving, we discovered more and more color. Some of our favorite stops were when we ditched our itinerary and opted to explore local backroads.
New England Fall Road Trip Tip #2 – Use Live Foliage Maps
Like I already mentioned, the color change can be unpredictable. Many websites offer live foliage maps that are updated daily to keep you updated on the best areas to see color. You can find one of those here.
New England Fall Road Trip Tip #3 – Get Off the Interstate
New England interstates provide many scenic views during leaf changing season. But you can’t always pull over on the side of the interstate to start photographing the colors. So, get off I-91 and explore the backroads – you won’t regret it. New England is full of quaint little towns and sites that you will never see if you stay on the interstate.
New England Fall Road Trip Tip #4 – Wake Up Early
The days in New England are starting to get shorter, with sunset occurring around 6 pm in the fall. Unfortunately, the fall colors are not visible in the dark. So, to maximize your leaf peeping day-light hours, get up with the sun. Never have I ever regretted getting up early for a sunrise.
New England Fall Road Trip Tip #5 – Visit During the Week
Extend your trip past the weekend to avoid the traffic and weekend crowds that flock to New England for leaf peeping and fall activities. We easily could tell a difference between Saturday-Sunday traffic at local sites and the following weekdays. There were a few times during the weekend that places were so packed that we decided not to fight the crowds and just kept driving. The week days were much more quiet and manageable.
Day 1 – Connecticut
After flying into Boston Logan International Airport and an overnight stay in Providence, we headed west to Connecticut. Kicking off our fall foliage tour, we stopped at Pachaug State Forest for some easy hiking & pond views.
Next, head to B.F. Clyde’s Cider Mill in Stonington, CT for some local hard cider or apple wine. This cider mill is only open seasonally and can become very crowded on the weekends. Cider making demonstrations are also available on Saturdays & Sundays.
Chatfield Hollow State Park is another great Connecticut stop for fall colors and a hike around Schreeder Pond. Here, you will find a mixture of pine trees and changing colors. Don’t miss the boardwalk over the wetlands.
For dinner, check out a local favorite, Lenny and Joe’s Fish Tale in Madison, CT for some delicious seafood.
Day 2 – Massachusetts & Southern Vermont
Day two will have a lot of driving and a lot of great views. Remember to stay flexible and make a stop anytime something sparks your interest. New England is full of small towns offering many small family-run shops and restaurants that are worth stopping at.
From Connecticut, drive north on I-91N towards Massachusetts. In Greenfield, MA get off the interstate and head west on the Mohawk Trail (State Highway 2), one of Massachusetts’ most scenic drives. Depending on time, plan to make stops at the Mohawk Trail State Forest and Mount Greylock (Massachusetts’ highest peak at 3,489ft).
Next, head north to Bennington County. This area has a very high concentration of covered bridges. Spend the rest of the afternoon exploring the county and check out the Bennington Battle Monument.
If time allows, take Kelly Stand Road for more incredible fall colors. Stop at Grout Pond for bright colors reflecting off of the water.
We ended our day at The Vermont Country Store in Weston, VT, near our Airbnb. This country store had EVERYTHING: gifts, clothes, household goods, local foods, and even penny candy. We settled on a bottle of local cider and some fresh fudge.
Across the street from the store, we discovered the cutest city park and spend a few minutes snapping a few photos of these beautiful orange trees.
Day 3 – Woodstock & Stowe, Vermont
Vermont is full of maple trees which turn to beautiful shades of gold and red when the weather turns cold, so this state is a must on your New England fall road trip. For day three, you will hit both Woodstock & Stowe, VT. Both of these quintessential towns offer so many spectacular colors and other typical fall activity favorites like cider mills and apple orchards.
Make sure you get up early, day three has a lot to see. Although, this day should probably be split into two days, we were able to cram it into one. Start your day by heading to Woodstock, VT.
On the way, make a quick stop at the Cornish Windsor Covered Bridge which is located on the border of Vermont and New Hampshire. This is by far the prettiest and longest covered bridge I have ever seen!
Next, spend a few hours in Woodstock exploring the Marsh-Billings-Rockefeller National Historical Park. This is a joint park with the Billings Farm which requires a tour fee but there are a lot of free options in the national historical park. Take a quick hike to The Pogue, another stunning pond surrounded by fall colors.
No visit to Woodstock would be complete without a drive by the most picturesque farm that New England has to offer, Sleepy Hollow Farm (listed in Google Maps as Elm Grove Farm).
Stowe, VT
After finishing up in Woodstock, head north to Stowe, VT. Stowe offers many leaf peeping hikes, charming shops, and fall activities.
On the way to Stowe, check out the Ben and Jerry’s Factory for a tour and a much needed ice cream break.
Right before reaching Stowe, stop at Cold Hollow Cider Mill for live cider pressing demonstrations and the best hot apple cider in the area. Do not forget to pick up a cider donut! You won’t regret it.
Time to burn off some of those ice cream and donut calories. Head to Smuggler’s Notch State Park. Keep in mind that this park closes for the season on October 14. Unfortunately, we visited on October 15. Bummer! We were still able to access the Bingham Falls Trailhead, which was a short 1 mile roundtrip hike to a waterfall.
Head back into town for a hike to Sunset Rock. Just like the name suggests, this short overlook hike is a wonderful place to watch the sun set over the town of Stowe. This beautiful view is a wonderful way to end your New England fall road trip.
Have you been to New England in the fall? Lease a comment below and let me know what was your favorite thing to see!
More Road Trip Adventures:
- Why Maine Should Be on Your Travel Bucket List
- Las Vegas to Furnace Creek: A Death Valley Road Trip
- 10 Can’t Miss Stops on the Oregon Coast
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