Have you always dreamed of taking a beautiful New England road trip in the fall? Then keep reading for the ultimate guide for your fall road trip experience. This guide will help you plan the perfect long weekend fall road trip through some of the most beautiful parts of our country.
This trip has been on my bucket list for years. So needless to say, years and years of research has been poured into this trip. I mapped everything out. Trying to get the most bang for our buck and for our time.
We only had 4 days to fit a lot in. So without further ado here is my guide to the perfect FALL in New England Road Trip.
*a little pro tip* The foliage is highly unpredictable. My best piece of advice is to plan to visit within the first two weeks of October. Book refundable rooms, maybe even on different dates, and be flexible. But if you book something during the first two weeks of October then you should be fine and will be able to see beautiful foliage.
Also start planning in advance. The earlier the better. Rooms get booked up quickly for these first two weeks which causes rates to skyrocket.
Note: Some of the links on this site are affiliate links. This means that if you click on the link and make a purchase, we may receive a small commission at no extra cost to you. This helps us to cover the costs of running this site and to continue providing you with valuable travel tips and guides.
Getting There
If you are flying, take the red-eye into Boston. Taking a late flight the night before Day 1 of your trip starts, ensures you will be there and that you will have the whole day to be able to explore on Day 1 of your trip. We flew into the Boston Logan Airport, landed around 11:30 PM, picked up our rental car and drove straight to our hotel for a good night’s sleep.
I believe a rental car is a must when in New England. You will want to drive to so many spots and have the ability to change course if need be. It just gives you the freedom to see as much of New England as you want.
Where to Stay
Like I said, we stayed in Boston. We like the proximity to the airport, especially when flying in late. We spent two nights in Boston (the first night after flying in and the next night). Here is a list of some of my favorite hotels in Boston to consider. We stayed at the Iris Hotel Boston on this particular trip and it was incredible.
There are so many amazing hotels in Boston. Check them out below.
If you would prefer to stay in Salem, as opposed to Boston. Here are some great hotel options. Be sure to plan very early in order to ensure room availability in Salem in October.
DAY 1 OF THE NEW ENGLAND FALL ROAD TRIP
SALEM, MA
Salem will be your first stop on your road trip. Take the quick drive up from Boston. It will take anywhere from 25 min to an hour, depending on traffic.
Must Do’s in Salem
The history and hauntings tour is a great way to see a bunch of sights in a few hours. The guide was so knowledgeable and had many interesting facts to tell us about the city. This tour will take you to the Ropes Mansion, Old Town Hall, The Witch House, The Witch Memorial, The Bewitched Statue and more. There were a lot of “Hocus Pocus” sites on this tour, so if you are a Hocus Pocus fan, then this tour knocks a bunch of them out. It was a nice, informative way to see a lot of the city in 2 hours.
The Salem Witch Museum is a must for first timers to Salem. Although the name can be a little misleading because it is more of a storytelling production than a museum, but still worth checking out.
If you are a Hocus Pocus fan, you will want to check out Max and Dani’s house. You cannot go in as this is a private residence and it can be quite tricky to find. But it will pull up on Google maps. Just remember to be respectful and stay in the street when getting photos.
Pioneer Village is a historical site that takes you back in time to the Puritan way of life. It is also where some of the movie Hocus Pocus was filmed. Be aware, it is only open on the weekends.
Also, add the House of Seven Gables to your list. This is the home in which the book by Nathanial Hawthorne was written.
Salem has so many great tour options as well. Tours are great and allow you to see so much with a knowledgeable guide. Check out the many tour options HERE.
Dining in Salem
Here are some amazing places to grab a bite to eat when in Salem.
You can easily accomplish all of this in one day and head back to Boston for dinner. Here are some of my favorite Boston restaurants.
I have a complete Boston travel guide for an amazing weekend in Boston. It gives you all of the Boston recommendations and will help you plan your entire Boston trip from top to bottom. If you ever decide to just do a Boston only trip, then this guide will be your best friend.
Day 2 OF THE NEW ENGLAND FALL ROAD TRIP
–WOODSTOCK, VT–
The quintessential fall town in New England is Woodstock. You truly feel like you have stepped onto the set of a Hallmark movie. It is cozy, charming and the perfect place to check out some amazing foliage in a beautiful town.
Where to Stay
We used Woodstock as our home base for 2 nights, while we explored Vermont. There are a few hotel options here, but the most well-known and most fabulous is the Woodstock Inn. The Woodstock Inn is a Michelin Key resort and spa. It is stunningly beautiful.
Other hotel options in and near Woodstock.
Must Do’s when in Woodstock
Visit the Middle Covered Bridge.: A beautiful covered bridge right in the middle of town. Easy to walk to and take photos of.
Visit Sugarbush Farm: an incredible working maple syrup farm. Come to this farm and learn how maple syrup farmers get amazing maple syrup to your table. Taste samplings of the syrup and different cheeses and shop around their cute gift shop.
Shop the local boutiques around town: There are so many charming boutiques to find the perfect Vermont souvenir.
Dining in Woodstock
DAY 3 OF THE NEW ENGLAND FALL ROAD TRIP
–STOWE, VT–
We drove up to Stowe, Vermont from Woodstock on Day 3. Our plans were to stay in Stowe the entire day, but we actually had gotten up so early and made it to Stowe early morning, so we were able to add a few more stops to our list on this day.
Stowe is absolutely beautiful and picturesque. It has to be a stop on your New England fall road trip.
Must Do’s in Stowe, Vermont
Visit Cold Hollow Cider Mill: grab fresh cider donuts and apple cider at this adorable cider mill, located just outside of Stowe.
Walk the Stowe Covered Bridge: this gorgeous bridge is located in downtown Stowe and makes the perfect picture spot.
Get photos of the famous Stowe Church: the white church that is in all of the photos you have ever seen of Stowe does not disappoint. Right up the road from the covered bridge is a great vantage point for getting some incredible photos of the church.
Take a ride on the Stowe Gondola: take this gondola up to the top of the mountain for an incredible view of all of the fall foliage. You can purchase tickets in advance online.
Shop around downtown Stowe: support the local shops and businesses in Stowe. They have some very charming stores to grab a couple of souvenirs.
Visit the Ben & Jerry’s Factory: take a walk through the flavor graveyard where all of the retired flavors have been “laid to rest”.
Visit the Trapp Family Lodge: Yes, the actual Von Trapp family from the Sound of Music. When visiting North America, the Trapp family fell in love with Stowe and decided to plant some roots there. This lodge has an incredible history and you can actually stay here.
Stowe has some fun tours and guided experiences you can do as well.
Dining in Stowe, VT
After we finished with our day in Stowe, we drove over to Burlington, Vermont and down the scenic highway 7. We were able to make some stops to see the beautiful Lake Champlain. We stopped at a roadside apple orchard, and of course, had to grab another maple creemee at Cookie Love.
The last leg of the trip back to Woodstock was through the Crossroads of Vermont Scenic Byway, and it had some of the best fall foliage. We stopped in Bridgewater at Ramunto’s Pizza for dinner and it was a fun little spot.
If you would like to stay in Stowe as opposed to Woodstock, you could easily do that as well. During peak fall months, most hotels require a minimum of 2 nights so you would likely need to choose Woodstock for 2 nights or Stowe for 2 nights, but you could easily do it either way.
Here are some top hotel choices in Stowe
DAY 4 OF THE NEW ENGLAND FALL ROAD TRIP
–KANCAMAGUS HIGHWAY TO KENNEBUNKPORT, MAINE–
Day 4 is going to start early. We got up super early from our hotel in Woodstock to head to Lincoln, New Hampshire to start our drive down the Kancamagus Highway. We arrived to the entrance of the Kancamagus Highway right around 7:30 AM. The Highway was at peak foliage. It took us about 3 hours to complete the 34 mile drive. There are so many beautiful stops, that you will want to allow enough time for that.
Must Do Stops Along the Kancamagus Highway
- Lincoln Woods Trailhead Suspension Bridge
- Hancock Overlook
- CL Graham Wangan Overlook
- Sabbaday Falls
- Albany Covered Bridge
We finished up the highway in Conway, New Hampshire and from there drove to Kennebunkport, Maine. This was the cutest, most charming coastal town in Maine.
In all honesty, we had planned on spending the last day and night in more of New Hampshire, but as time drew closer, we were seeing that the foliage in more northern New Hampshire was already starting to fall. So we decided last minute to change our plans up a bit, and I am certainly glad we did. Kennebunkport was an incredible stop to add to our road trip.
We spent the rest of our day exploring Kennebunkport.
Must Do’s in Kennebunkport
Walk through Kennebunkport Historic District. Here you will find charming shops, incredible views and restaurants
Visit St. Ann’s by the Sea Episcopal Church
Walk along Ocean Avenue. Here you can the see the Bush family estate of Walker’s Point.
Dining in Kennebunkport
Where to Stay in Kennebunkport
The Boathouse Waterfront Hotel is a stunning hotel with views of the pier. There is also an amazing restaurant located right inside the hotel.
The Colony Hotel is another incredible option. Full of that coastal New England charm.
The Kennebunkport Inn is such a charming hotel with nautical vibes. It just screams Maine.
Sadly, after our time in Kennebunkport, it was time to head back to Boston that morning and fly home. If you have never done a fall New England road trip, then I highly suggest adding it to your bucket list. It is such an incredible experience. Even if you are short on time and don’t have an entire week to spend, you can easily do this over a 4 day weekend. Yes, you will be busy, but it is worth it.
Here is a map of your entire New England fall road trip.
WHAT TO PACK
If you need outfit inspiration for your fall road trip through New England, then I’ve got you covered on that as well. Think chunky sweaters, lightweight jackets and comfortable, but cute shoes. Here is some inspiration below. Click on each picture to shop the outfits.
Here are some of my favorite go to travel essentials from Amazon. These are my tried and true essentials that come along on every trip with me.
Happy travels friends!
Leave a Reply