Last month we took a fall New England road trip to see the colorful foliage that the region is known for. This trip is probably one of the best vacations Ted and I have taken together. We love fall, nature, and history and this trip combined these elements perfectly for us. It definitely was tricky planning this trip because the possibilities were almost overwhelming but luckily I had a good sense of the area since I’ve spent many summers in New England as a kid.
While on the trip I received so many questions about our itinerary, which towns we visited, and the route that we took. It seems that I’m not the only fall lover around and that a lot of folks have been wanting to do a fall New England road trip. So to help you plan I’m sharing where we went and some tips for the way! Keep reading and start planning your New England road trip for next year.
When to go
First things first. When is the best time to go? I did a lot of research on this and typically the first two weeks in October are the best times to visit if you want to see the fall leaves at their peak. We went between October 9 – 14, which was perfect timing because the leaves were glorious.
Day 1
Fly into Boston & Car Rental
In our usual fashion we took an early morning flight and arrived in historic Boston around 10am local time. From there we quickly picked up our rental car, got settled, and set off on our adventure.
John Adams House
Ever the history nerds, Ted really wanted to see the John Adams house which is in a town called Quincy. It’s just a 20-30 minute drive from the heart of Boston. We toured their homes and got an appreciation for my favorite founding father John Adams and his first lady Abigail. They were a remarkable couple for their time. My favorite bit was seeing their family library.
Drive to Concord, MA
Just about an hour’s drive from Quincy we made our way to where that “shot heard round the world” was fired. You may be seeing that there’s an American Revolution theme to this trip here….
I wanted to visit Concord because its not only historically important but it’s a bit of a literary mecca for American literature. It’s also the home of Louisa May Alcott (Little Women), Ralph Waldo Emerson, and Henry David Thoreau, and the ever famous Walden Pond.
The town was lovely and I wish we could have spent more time there. We saw the first battle site of the Revolution, ogled the home where Little Women was written, and enjoyed the historic homes in the neighborhood.
Drive to Salem, MA
So our Day 1 also happened to be my 30th birthday. And for some reason this October baby has always dreamed of spending a birthday night in the spooky town of Salem, lauded for its history of witches and magic. We spent the night at the Hawthorne Hotel, which I later found out is one of America’s most haunted hotels.
Day 2
Salem, MA
We spent most of our second day exploring Salem, learning about its history, and enjoying the town’s Halloween décor. They have embraced their witchy history and its encompasses much of the town’s identity! I loved Salem so much that I made it its own separate blog post so for more in depth details on what to do, where to stay, and where to eat, check that out here.
Drive to Jackson, NH
Around 3pm we left Salem and made our way to New Hampshire. This is what I love about New England – everything is so close together. And you can make your way to different states pretty quickly.
Eagle Mountain House & Golf Club
I have a thing for these old historic hotels. They have a timeless elegance to me, and the White Mountains of New Hampshire are known for incredibly large, and luxurious hotels. I would come back here in a heart beat. We ate in the hotel restaurant that evening and enjoyed a cozy night by the fire.
Day 3
Drive to the top of Mount Washington
A few hours drive from Jackson is the famous Mount Washington. I remember visiting with my family as a little girl, and this windy and frigid mountain top is known for two things. It’s the tallest peak in the Northeast and it’s home to literally the worst weather on earth. Seriously.
The drive up there is not for the faint of heart and follows miles of narrow mountain roads. But the views are incredible and so worth it. The top of the mountain has an observatory, restaurant, and museum that tell the history of the mountain, its trails, and the stories of the many hikers who have lost their lives trying to reach the summit. This mountain teaches you to respect nature!
Mount Washington Hotel
On the other side of the mountain is one of the grandest historic hotels – the Mount Washington Hotel. It’s a great place to visit. It has a golf course, restaurants, amazing views and some good hiking. Ted and I did a three mile loop in the trails behind the hotel and relaxed in the gorgeous lobby before heading back to Jackson for the night.
Visit scenic sites along Rt. 302
Driving around the White Mountain area stick to the famous Route 302, and you will see so many overlooks, scenic sites that you have to take time to enjoy. Ted and I stopped to get out of our car and take pictures so many times because the views and fall colors were just incredible. Take your time driving around and stop in the small towns and sites that peak your interest.
Dinner at the Wildcat Inn & Tavern
Jackson is a very small town so the dinner options are limited, but we found this tavern and it was the perfect place to spend a quiet night. And the food was amazing.
Day 4
Drive to Woodstock, VT
We left the mountains of New Hampshire and made our way to the rolling hills and farms of Vermont. I purposely put in very little structure to this part of the itinerary because I wanted us to drive around stop at the small towns along the way. We followed Route 302 and then Route 91 down. I’m copying and pasting our route below but we stopped at the following towns. Some looked historic, some had covered bridges, and some looked like good places to pick up snacks. All were cozy, quaint, and perfectly autumnal.
- Sugar Hill, NH
- Bath, NH
- Haverhill, NH
- Norwhich, VT
Explore Woodstock, VT
This town looks so picture perfect, it’s hard to believe that it’s real. During the fall, tourists flock to enjoy the farmer’s markets, fall festivals, apple picking, pumpkin patches and the historic small town atmosphere that makes the town famous. It really is beautiful and its lovely to pick up a maple ice cream and walk around the shops and enjoy the colorful leaves.
Kedron Valley Inn & Ransom Tavern
So the Kedron Valley Inn is located in South Woodstock, just a 20 minute drive outside of Woodstock. It’s in an extremely small town which is why I was drawn to it. It’s been operating as an inn since 1822. The building was recently renovated and they did a wonderful job. The look is a clean, elegant American chic.
There are no other food options in town (it’s that small) but that was okay because in the inn is the Ransom Tavern. We had their oven cooked pizza and it was incredible. Despite being in a very rural spot the restaurant was packed the whole night. That’s how good it is.
Before bed Ted and I wandered some of the country roads and watched some horses grazing in a nearby field. It really was cool to see what quiet, rural life can really be like.
Day 5
Sleepy Hollow Farm
You may not know it’s name, but I promise if you’ve ever been on Instagram you will likely have come across a picture of this farm. It’s famous in the area for how perfect it looks so I had to make a visit over. It was worth it – just look at these pics. We walked about a mile together there from the road and enjoyed the small farms and fall leaves along the way.
Fort Ticonderoga
Back to our Revolution theme Ted wanted to visit Fort Ticonderoga which was just a two hour drive from Vermont. It was located in New York actually so we made the drive over. We took the ferry back into Vermont which shaved off forty minutes from our trip home and I would recommend it for the experience. Especially if you have kids with you, they’ll love it.
Visit Vermont Farms
Along the way back home we stopped at a bunch of farms in Vermont and just enjoyed the scenery. I normally hate driving, but this is one trip that I actually enjoyed doing this. We picked up some delicious fresh apple cider and maple candy that were delicious.
We flew out the next morning so our scenic visits took the full five days. I would have loved to tack on more, but think the minimum of five days were a good fit.
Additional Tips
- Book your hotels early. I cannot stress this enough. Once you book your flights and settle on dates book your hotels the same day. The prices are usually doubled because of the peak tourist season due to the leaves and the best towns are small and sell out of lodging very fast. Often times what will be available hotel wise will dictate your trip’s itinerary.
- Don’t keep things too structured. I had list of towns that we wanted to hit, but it was the ones that I didn’t have on my list that we ended up enjoying the most. If you want to stop somewhere, do it ! These small towns appreciate the business of tourists too!
- Dress in layers – the mornings and nights were very crisp, but in the sunshine the days were warm.
Our Route
I’ve mapped our New England road trip on google maps in case you’d like to follow our route. Keep things flexible and make sure to stop whenever you see something interesting, you’ll discover the best, small spots this way.
So that’s it. I’ve been wanting to visit New England in the fall all my life and I’m glad I did it. We got so lucky with the weather and that the foliage was at its peak. It made everything seem golden, the air was crisp, and it will be one of those trips I’ll never forget.
