The Ultimate Fall New England Road Trip

Nothing beats a crisp autumn morning surrounded by all the vibrant colors of Fall. One of the absolute top locations to enjoy that burst of color is in New England. It can be a very busy time of year, but with a little bit of careful planning, you can enjoy the best spots in New England and even avoid some of the crowds. 

Planning a trip in the fall can be a little unpredictable because the leaves don’t always change the same time every year. We used a couple of different sources to estimate when we thought the peak season would be in the area, and booked about a week long trip to give ourselves just the right amount of time. The further north you go, the earlier you’ll want to start your trip. And its always a good idea to give yourself a little flexibility incase things change. 

Here is the full Itinerary we planned for our New England road trip in Early October. 

Day 1 

Travel Day & Arrive in Stowe, Vermont

There are a few options for flying into this area. We fly Southwest almost exclusively, so the closest airport was Manchester, so we flew in mid-day, picked up our rental car, and made our way to Stowe, Vermont. 

We booked our accommodations at the Best Western in Waterbury-Stowe. The plan to go to Vermont was a last-minute decision, so we had limited options, but honestly the BW was still great, they even had a little covered bridge right off the parking lot. 

Best Western Waterbury – Stowe

Day 2

Exploring Stowe Vermont

Stowe Vermont is a popular skiing destination in the winter time because of the snow covered slopes and consistent winter temperatures. But Stowe is also known as a 4 seasons destination, with plenty of things to draw in visitors during the rest of the year. The Ski Resorts are ready to help visitors in the Spring and Summer find alternatives like mountain biking and hiking. We picked this city as the first stop on our Fall road trip because it was geographically convenient, but also boasts some of the most quintessential fall themed activities.

Downtown Stowe makes you feel like the main character of a Hallmark movie, with the historic buildings, flower lined store fronts, and the old white church sitting in the middle of it all. We started our day here, walking the downtown area and enjoying the crisp fall weather.

The next stop for the day was the Cold Hollow Cider Mill. In their own words, Cold Hallow Cider Mill is a “Charming spot with a bakery known for cider donuts, plus a market for syrups & other Vermont goods.” And we got all of those things, an order of cider doughnuts, a gallon of cider to take on the road, and a maple creemee, which is Vermont’s version of soft-serve.

The final stop of the day was at the Ben & Jerry’s Ice Cream Factory. The factory holds tours, and has a tasting shop, but unfortunately it was not open the day we visited. We did however still get the chance to see the Flavor Grave Yard, and snap a few pictures.

Day 3

Kancamagus Highway

It is time to leave Vermont behind us and headed into New Hampshire. We focused our time in the White Mountains, more specifically close to Mount Washington. We pick a super cute A-Frame cabin on AirB&B to stay in, and right from the bedroom window we caught a glimpse of the fall colors surrounding us.

We decided to start our time in New Hampshire with a scenic drive along the Kancamagus Highway. This is about a 50 mile stretch that travels through the White Mountain National Forest. This drive is insanely popular to drive, so if you can, going during the week helps minimize the crowns and traffic you’ll experience. There are multiple pull out stops, overlooks, and hiking trailheads along this drive. We actually downloaded an audio guided tour to help us both navigate the area, and learn about the history along the way.

To top off the day, after you’ve made your way down the Kank, as the locals call it, its time for a stop at the White Mountain Express Gondola. This 1.3 mile scenic ride takes you up Loon Mount, for a view back at all the amazing colors we just saw in the mountains. You can grab a bite at the Summit Top Cafe, and wrap up your day of amazing views.

Day 4

The Flume Gorge

Today, it is time to put those hiking shoes on. But first, Bagels. No hike is ever official until you’ve loaded up on carbs, so a stop at White Mountain Bagel Co is the first thing you should do this morning. Serving up bagels and coffee right next to the White Mountain’s Visitor Center, you know this place has to be good.

Once you are caffeinated up, its time head to the Flume Gorge, located inside Franconia Notch State Park. The Flume Gorge is a natural gorge extending 800 feet horizontally at the base of Mount Liberty, New Hampshire, United States. Cut by running water over millions of years, the gorge features walls of Conway granite that rise to a height of 70 to 90 feet tall and are as narrow as 12 to 20 feet. The area required a reservation, and the entrance is $16 per person. So, as soon as you have your dates nailed down, it’s time to book the time slot.

The rest of the day should be spent exploring some of the covered bridges in the area. If you are like us, and from a place where it does not snow, not ever, it can be kind of confusing to see these covered bridges all over the North East. But these bridges were built, many of them around the 1900’s, in order to protect the bridges from snow and winter weather. With more modern construction today, its less stressful on the infrastructure when it snows, so these bridges have now become a picturesque reminder of the past.

Day 5

Mount Washington Cog Railway

Today let’s ride the Mount Washington Cog Railway. There are 3 ways to get to the summit of Mount Washington, you can hike, you can drive or you can ride the Cog Railway. We opted for the cog, because driving seemed scary, and we didn’t really have time to train to hike a four-thousand footer this trip. The Cog is the world’s first mountain-climbing cog railway, built in 1869, and beating out the Pikes Peak Cog Railway by almost 20 years. Built to carry the influx of tourists New Hampshire had started to see thanks to the continental railroad, the Cog carrier hopeful travelers to the summit to enjoy the views just like it does today.

The Summit of Mount Washington is quite impressive once you reach the top. The trip takes about 45 minutes to an hour depending on which locomotive you choose, steam or biodiesel. And once you are there, its time to put on a coat and jacket. The weather at the summit is almost always significantly colder and windier than at the base. Mount Washington is where the highest land speed wind record was ever recorded, on April 12, 1934, the wind gusted to 231mph. Consistently you’ll face 45 to 60 mph winds, on a calm day. They lovingly refer to Mount Washington as home to the worlds worst weather, so its definitely a must do stop.

Day 6

Portland for a Day

Portland is not necessarily known as a fall destination, but if you are anything like us, you’ve got to squeeze in a visit to a lighthouse any chance you get. We headed across Maine from New Hampshire, and enjoyed a nice leisurely drive, stopping at some scenic points along the way. Once we reached to coast we stopped by the Portland Head Lighthouse. There is also a lobster truck in the parking lot, so this is basically the full extent of Maine in one fell swoop.

We also boarded a tour with Lucky Catch Cruises, and spent the rest of the day becoming lobster fishermen. This was such a unique experience, and we caught them at the end of the season, another few weeks and they would have been closed up for the winter.

We didn’t have a chance to fit it into this trip, but if you have a few more days in Maine, the one area known for its brilliant colors in the fall, is Bar Harbor, more specifically Acadia National Park. This will definitely be on our list for next time, but will require a few more days to explore and enjoy the area.

Day 7

The last day of our trip is specifically for the spooky enthusiast among us. We headed into Massachusetts, and stopped at the world famous haunted icon of Salem. Famous for the witch trials of 1692, Salem comes alive in the days and weeks leading up to Halloween. Its a great stop if you are into history and the paranormal.

We visited a couple of different sites, including the Witch House, which was actually the home of Jonathan Corwin, a judge during the trials. The Witch House is the last standing structure that dates back to the trials, and has been preserved to reflect how the residents lived during the times of the trials. We also visited the Salem Witch museum, which gives a very through, although hard to hear, retelling of the Witch Trials.

The city of Salem has really embraced the history and interests of the visitors and offers many different types of ghost, witch and paranormal tours. They also have streets lined with boutique shops with candles and spell books and anything to fill your witch craft spirits. Its definitely a perfect end to a fall road trip.

If you haven’t had a chance to check out our video from this ultimate fall road trip, view it here:


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