Our 2018 New England Fall Trip: Vermont, Boston and Yale

I’m writing this post just after returning from one of the best trips we’ve ever taken. It’s always been a dream of my wife and I to take a New England fall trip. So, we headed to Vermont to see the fall colors. And, we also took in some history along the way too.

In all, we were gone for a week. We spent the night in four different states. And, we traveled through 10 states during the weeklong trip.

While most of this article will focus on our time in Vermont. We spent the most nights there and that’s where the fall colors were, I’ll also include some brief tidbits on our time in two other spots we stopped at too.

Our New England Fall Trip

We live in eastern Tennessee, near Knoxville. While we have our own fall colors and the majestic Great Smoky Mountains, it’s still not the same as going to New England. The terrain is gentler and more serene. It’s a different kind of beauty.

To get to Vermont, we drive 1,000 miles northeast (that’s 14 hours in the car with two children under the age of 4). Since we don’t know the next time we will be up this way, we decided to see some other sites along the way.

I have a mountain of hotel points banked up from my old job. So we paid for our lodging with points and only had to pay for gas, food, and sightseeing. Usually, we book a place for a week using Airbnb because we like having a full kitchen and the privacy that comes with renting a full house. But, we changed our reservations twice during this week based on the weather and the local happenings, so the flexibility of hotel points and last-minute cancellations was nice this trip.

Below is a basic route we took during our trip. We started in Lancaster County, Penn. and ended in Concord, Mass.

New England Fall Trip

We did our best to avoid major metropolitan areas to avoid traffic and hopefully see more scenery.

Lancaster County, PA

We used to live in semi-rural Kentucky where the Amish and “English” (what they call non-Amish) essentially live side-by-side. So, we’ve seen our fair share of Amish families. But, we wanted to see what Lancaster County was all about.

I’ll be honest, this was our least favorite vacation stop. To sum it up in two words: tourist trap.

I thought we were back in Pigeon Forge and Gatlinburg with the gimmicky gift shops and attractions. We did drive a little bit of the countryside and enjoyed the scenery.

One saving grace is that we saw author Sherry Gore buying an ice cream cone and then driving off in her iconic blue convertible VW Beetle. Nobody stopped her, but it’s cool to see a local celebrity of sorts.

Yale University and Milford, CT

Originally, we planned on spending two days in Pennsylvania over Columbus Day weekend. After the Lancaster letdown and discovering our hotel was in a rougher part of Reading, we decided to only stay one night and cancel our second night.

We found a Holiday Inn Express in Milford, Connecticut that had rooms available for points. In Milford, there’s Silver Sands State Park on Long Island Sound. During low tide, you can walk across a sandbar to Charles Island. If you’ve been to Bar Harbor, Maine, they have a similar landmark.

Silver Sands State Park

The sandbar you can walk across to Charles Island during low tide.

In nearby New Haven, CT we took a campus tour of Yale University. Although there isn’t an elitist WASP bone in my body, it was neat to visit an Ivy League school. The Old Campus is very scenic and we wouldn’t have know where to explore the campus without the tour.

There were some fall colors at Yale, but it would have been better in one or two weeks. We visited Columbus Day week as it was our fall break back home. So we’ll admire what we saw since it’s better than only seeing green leaves back home. Plus, our fall colors are good but not great.

Also, the fall colors in northern Connecticut were really nice. There was a lot of bright yellows on the drive up to Vermont.

Vermont Fall Colors

Vermont was the primary purpose of this trip. We stayed at the Holiday Inn Express near Springfield, Vermont in east-central Vermont. It’s right on the I-91 on the Connecticut River that separates Vermont from New Hampshire. Although we spent most of our time in Vermont, we rode the Sugar River rails-trails bike trail in New Hampshire. Plus, we took a few back roads in New Hampshire too.

I’m not a leaf expert and I’m sure the quality of fall foliage varies on the year, location, and time of the month. The colors were good, but we had to drive about an hour from our hotel to see better color.

To be honest, the best color we saw was on the drive to Boston. Sadly, it was raining hard so we couldn’t get good pictures but it’s the peak colors and scenery we were seeking. On Highway 101 between Keene, NH and Nashua, NH is where we saw the best color. You go through one or two small towns. And, at one point the road borders a lake that would make a good stopping point too. This is the Monadnock Region of New Hampshire.

Vermont Fall Colors

Some fall colors near Grafton, VT (Credit: My Wife!)

Manchester, VT

In Vermont, one of the best places we saw fall color was in Manchester. We were still a few days early from the peak colors, but it was better than near our hotel.

We also took in some history at Hildene Mansion. It’s a 400-acre estate of Robert Todd Lincoln (President Lincoln’s eldest son). It’s located on the dividing line of the Taconic Mountains of New York State and Vermont’s Green Mountains.

Fall Colors Near Manchester, VT

Fall Colors near Manchester, VT Credit: My Wife

Covered Bridges

Vermont and New Hampshire are known for their brown covered bridges. In some ways, it’s a scavenger hunt. We were able to drive across one in Vermont. On the New Hampshire rails-to-trail, we rode our bike across another.

Vermont Covered Bridge

A covered bridge in Vermont Credit: My Wife

Sugar River Trail in New Hampshire

Getting ready to bike on a covered bridge on the Sugar River Trail in New Hampshire.

Lexington and Concord, MA

We finished our trip with 1.5 days in Lexington and Concord, Mass. Almost all of the leaves were still green, but we love history. This is because we have in interest in the Revolutionary War and the notable authors who lived in these villages including Emerson, Hawthorne, Thoreau, and (my wife’s favorite) Louisa May Alcott.

We’re saving Boston for a different trip, but we wanted to see these “suburbs” since we were so close.

Some of the sights we saw included:

  • The North Bridge (where the “Shot Heard Round the World” took place)
  • The Old Manse (adjacent to the North Bridge and home to Emerson and Hawthorne)
  • Orchard House (home to Louisa May Alcott and the setting of Little Women)
  • Lexington Green (The first official skirmish of the Revolutionary War)
  • Gravesites of Emerson, Thoreau, and Alcott (they’re all buried on Author’s Ridge in Sleepy Hollow Cemetery)
The North Bridge

Where “The Shot Heard ‘Round the World” Occurred

The Buckman Tavern

The most kid-friendly attraction we visited was the Buckman Tavern on Lexington Green.  If you have small children, you know how historical tours are already somewhat taxing. Being with a snobby crowd or tour guide doesn’t help.

We didn’t experience this at the Tavern. In fact, the staff went out of there way to make our children feel welcome.

This is where the militia met before the opening shots were fired. The tour is a self-guided 25-minute audio tour. On the upper floor, they have a historical display that shows how fast the information spread across the colonies after the Battles of Lexington and Concord.

Great Brook Farm State Park

While we spent our time in Lexington and Concord, our hotel was in nearby Chelmsford. On the way back to our hotel we found a scenic oasis. If we come back to the Boston area, we’re going to carve time out one day to revisit Great Brook Farm State Park.

For starters, this park has a working dairy and a place to buy ice cream. One of the few splurges we make while traveling is on ice cream. Not to spoil your appetite, but you can also buy hamburger patties and cow manure on-site too.

This state park also has 900 acres of hiking and biking trails. This is the main reason we want to come back to this park. There’s also a bike trail in the Minuteman National Park area that connects Lexington and Concord, but we enjoyed the few trails we took in this park. They were more secluded and we saw a good mix of trees and babbling brooks.

New England Fall Trip

One of the babbling brooks on the 900 acre Great Brook State Park in Chelmsford, Mass.

Other Crazy Things We Learned On This Trip

After this trip, my wife and I want to take an annual fall trip to New England.

To see more fall colors, we would definitely explore either upstate Vermont. Or, spend more time in New Hampshire (either the upstate White Mountains or the Monadnock region we drove through)

But, these are some other random factoids, I didn’t know before we left:

  • People in New England are nicer and friendlier than we imagined (they have a generalization of being snobby from us Southerners)
  • Upstate New Jersey is surprisingly rural (we thought it’d be an endless suburb of New York City…kinda like northern Virginia is to D.C.)
  • It costs $15 to cross the George Washington Bridge, but you get a nice view of the NY Skyline with less traffic
  • New York State calls their rest areas “text stops” (I’m assuming AT&T indirectly sponsors them)
  • The Massachusetts highways information signs remind you to inspect your smoke detectors when there isn’t road work going on
  • Exits aren’t based on the actual mile marker (I.E. Exit 5 is the 5th exit vs. being at Mile Marker 5)
  • To stump the house tour guest, ask this question, “Who framed the pictures?”
  • All the houses seem more upkept than here (even those of blue-collar families)

Also, I don’t know what the typical fall weather in New England is like. For our week, it rained one day. The other days, it was cloudy with a cold drizzle until lunchtime. From about 2 p.m. to sunset, the sun popped out and it was enjoyable to be outside. It was like this in Vermont, Connecticut, and Massachusetts.


We loved our New England fall trip and want to go back again. Next time, we want to visit other states to compare the similarities and differences.

What’s your favorite New England fall foliage spot?  



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