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  • Writer's pictureMichael Acevedo

A Pedacito Of Leaf Peeping Road Trip Through Boston, Plymouth, Brattleboro, Manchester, Killington

Updated: Sep 23, 2022

After over a year of not traveling, I knew that my next trip had to be one that was filled with some of the things that I love about travel: food, nature, and quality time. On our last trip, we did an incredible road trip to several of the national parks in the western United States and we wanted a similar experience but with a new location.

Our itinerary consisted of a weeklong road trip through New England (the northeastern United States) to experience the dramatic change of the foliage from green to amber to orange and to red; an event referred to as "leaf peeping".

Map of our leaf peeping road trip through New England
Map of our leaf peeping road trip through New England

Having grown up primarily in Florida, I had never experienced the foliage change because our weather doesn't change enough to trigger this in our trees. Frankly, Florida doesn't have much by way of seasons. In general, we have two seasons: hot and rainy, and less hot and rainy.

What Is Leaf Peeping?

A quick overview on "leaf peeping". I didn't know that this term existed but it refers to the exodus of tourists, mostly other Americans, who flock to New England to witness the foliage color change during this time of year. The color change occurs over a period of about a month or so and is rated from "early peak" to "late peak", with "peak" being the height of the color change.

Timing your trip can be tricky (everyone wants to be there at the peak) and you have to use a mix of research and a bit of luck to experience this. By doing a road trip in this region, we were able to experience the full spectrum of the foliage change and could not have been more mesmerized by the sheer beauty that nature can conjure up as it prepares for the winter.

We decided to plan our trip around a cheap roundtrip flight that we found from Orlando, Florida to Boston, Massachusetts, departing October 14th and returning on October 21st. We felt that a road trip through Vermont, New Hampshire, and Maine were our best options for seeing the full spectrum of the changing colors - we were right.

Exploring Boston & Plymouth

We arrived in Boston during the evening so we only really wanted to get settled into our hotel, pick up our car, and go out for dinner; the next day we wanted to do as much exploring as we could. We drove about 45 minutes south of Boston to Plymouth to visit the region where the first settlers decided to make the "New World" their home.

Plymouth is a lovely town that has a lot of charm, far beyond a couple of historic landmarks that make this place famous. While here we also took a look at the "Mayflower II", a replica of the ship that the pilgrims took across the Atlantic to escape religious persecution in Europe. It is docked alongside fishing and leisure vessels on the beautiful bay in Plymouth.

Our next stop was a historic portrayal of what life was like for the pilgrim settlers. I was super excited to go to the Plimoth Patuxet Museums because of their walking trail that consists of recreated common structures for the indigenous and pilgrim populations that called this region home.

After our lovely visit near the cape, we headed back to Boston to walk the Freedom Trail, which is a path consisting of historic landmarks throughout the downtown area. Each of the sites played an important role in the creation of the United States. We didn't spend a ton of time at each location, which can truly be an all-day event, but we did enjoy our quick visit to most of the landmarks.

Exploring Vermont - Day 1

Most of our time in New England was spent driving through the gorgeous Vermont countryside and stopping at various small towns along the way. This leg of our journey would take us north, allowing us to witness the transition from Early Peak to Peak fall foliage. The temperatures also became much more desirable, requiring light jackets during the day.

Along the way, we stopped at Grafton Village Cheese in Brattleboro, Vermont for an afternoon picnic sampling some incredible local cheese. This cheesemaker has several locations, but this location is special because it is situated next to a farm and has gorgeous views. Unfortunately, we could not watch the actual cheese making due to COVID restrictions, but it was still a wonderful visit.

After our picnic, we continued north toward Manchester, Vermont. Our next stop was Hildine, the summer home of the Lincoln family built by the eldest son of Abraham Lincoln. The house was lovely and the property was stunning. The nearby town itself is worth a visit and has lots of options for visitors.

The highlight of this stop was the gardens in the back of the mansion which featured stunning views of the valley and mountains that were starting to show the beautiful colors we were searching for.

We ended our first day of road-tripping in the town of Killington, Vermont, which is a ski town about midway up the state. Having gotten a taste of the color change we were excited for the next day as we were going to head north on the beautiful Route 100 toward our next stop in Burlington, Vermont. More on that in the next article.


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Unknown member
Nov 05, 2021

What an amazing trip!

Michael Acevedo
Michael Acevedo
Nov 12, 2021
Replying to

It was so great! I can't wait to share the rest of it with everyone.

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