The Ultimate 7 Day Itinerary to New England in the Fall

October 27, 2023

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The Ultimate 7 Day Itinerary to New England in the Fall

A couple of weeks ago, our family flew to New England to see the fall foliage, and it was a DREAM. Everything you’ve heard about New England’s beauty and charm is true. But where are the best spots for leaf peeping? What activities should you do? What towns are good for shopping? Where should you stay? That’s why I created this ultimate 7 day itinerary to New England in the fall!

The entire time while we were driving in the northeast, I couldn’t take my eyes off the trees. The contrast of the red, yellow, orange, and green leaves were breathtaking.

I already want to go back next fall!

Although the changing leaves are most definitely a highlight, there are also lots of other things to do like hiking, seeing history up close, shopping for souvenirs in the cutest towns, drinking maple lattes, eating apple cider doughnuts and pumpkin waffles, going apple picking, and so much more.

During our trip, I took meticulous notes and considered my own experiences along with the research I’d done online. I also had several friends who went to New England, so I got to pick their brain about it, too. With that being said, this list is pretty extensive, and I’ll also have follow-up posts about the best places to eat in New England and what to wear.

street in downtown Stockbridge, Massachusetts with sidewalk, trees, white picket fence, and flag

If you’re able to go to New England in the fall, DO IT. I can’t recommend it enough, and I’m excited to share my itinerary and guide so you can have as much fun as we did!

When is the best time to see fall foliage in New England?

There are lots of factors that affect the color of the leaves, so be sure to research when peak season is. You can follow along on this fall foliage calendar to see when leaf-peeping is the best and modify your itinerary based off of it.

three people sitting on a plane going to New England

For our trip, we flew into Boston, then drove north and essentially worked our way down to the southern parts of New England. It definitely gave us the best chance at spotting the best colors. I’ll be sharing info on exact locations later in the post!

During the first few days we were in New England, we had blue skies and sunshine, but it quickly turned rainy, cold, and cloudy. At first, I was disappointed, but our tour guide actually told us this weather helps the leaves pop more! I could definitely tell a difference and was so happy to see the vibrant colors…

I think the most stunning leaves we saw were in New Hampshire along the Kancamagus Highway. This stretch is 34.5 miles of pure beauty. Whether it was the fall colors alongside the rocky rivers, the trees that formed a canopy over the highway, or the scenic covered bridges, there’s plenty to ooh and ahh over.

Not only is the drive gorgeous, but there are many photo stops also. We stopped three times: at Albany Covered Bridge, Lower Falls, and Wangan Overlook. Read more below about these specific stops and what we loved most about them!

Don’t miss the best fall foliage spots in New England! Get my FREE map here!

How to plan a trip to New England in the fall

Like I said earlier, pay attention to the foliage calendar and try to plan around peak season.  Our trip was from October 13-20, but I have friends who went in early October and also friends who plan to go in late October.  

Fall is New England’s busiest time of year since lots of tourists travel to see the leaves. Be sure to book hotels and places to stay in advance if possible!

Before I move on and give you an itinerary and specifics, I’d like to share a helpful piece of advice: The leaves are absolutely stunning, but don’t be devastated if your timing doesn’t perfectly work out. New England is an incredible place, with kind people and lots of fun activities. Focus on that and then let the leaves be the icing on the cake. It will save you so much stress and help you appreciate your trip even more!

The Ultimate 7 Day Itinerary to New England in the fall:

Day 1 – Boston to Southern Maine and Bar Harbor:

If you’re like us and flew into Boston or if you start your road trip there, then the drive from the city to Bar Harbor is about five hours. BUT, if you split it into other excursions, it won’t feel so long!

Though our first full day in New England was mostly driving, we explored southern Maine along the way.

kittery trading post in Maine

Our first stop was Kittery Trading Post. I’m not usually a big shopper when I travel, but I’m so glad we stopped here! They had lots of great (and inexpensive) souvenirs as well as name-brand shopping (Carhartt, Columbia, Patagonia).

Nubble Lighthouse

We then drove through what the locals refer to as “The Yorks” to get to Nubble Lighthouse. Though no one lives in the lighthouse anymore, there is still a lighthouse keeper who maintains the grounds and the structure. (On our way, we watched this short informational video about the lighthouse keeper.)

We had beautiful blue skies and sunshine when we went and were able to get picturesque pictures against the backdrop of the ocean and Nubble Lighthouse.

Kennebunkport, Maine

For lunch, we spent time in the town of Kennebunkport, which was so cute! They had lots of shopping—the candle shop and bookstore were a couple of favorites for us. After we left Kennebunkport, we drove around the outskirts of town, and I fell in love with the style of the houses! We also drove by Walker’s Point Estate (aka the Bush Compound).

As a side note and helpful tip, if you’re driving, a good spot to stop for a few minutes is the Irving /Circle K Gas Station on Moosehead Trail in Newport, Maine. Not only is it a good place to fill up your car, but they have multiple bathrooms and great snacks.

We made it to Bar Harbor, Maine that evening and stayed at the Acadia Inn.  

Day 2 – Acadia National Park and Bar Harbor, Maine

Bass harbor lighthouse

Bass Harbor is a beautiful spot, and while most people go at sunset (making it crowded and hard to find parking), I’d recommend going at sunrise instead. It makes for better pictures, anyway, because you aren’t backlit like you would be at sunset.

Fun facts: Bass Harbor is the first place in the United States to see the sunrise, and the lighthouse here is the Windows default desktop background.

looking out at the top of Cadillac mountain

After you watch the sunrise, drive over to Cadillac Mountain in Acadia National Park. Be sure to make a reservation if you’re driving to the top (do this at in advance. The 8am reservation is usually easy to get!

Our excitement for the day happened as we traveled up Cadillac Mountain and came upon a car accident. We were forced to turn back and take an alternate route. Keep in mind that these roads are narrow, and they’re quite literally on the side of a mountain—and we were in a giant motorcoach. The people in our group held their breaths as our driver inched the bus down the side of the mountain, but she did it perfectly—and even missed a road sign by about an inch-and-a-half. In fact, our driver was so skilled, she showed the other tour bus behind us how to back down. An exciting morning for sure.

Cadillac mountain in Maine

The top of Cadillac Mountain was a favorite of ours. Words and pictures don’t do it justice.

Oftentimes, it’s cloudy and rainy in Maine, but our prayers for no rain were answered, and it was a clear and beautiful day for us (it is cold and windy up there, though, so bundle up!). We could see several states and even Canada from the top of Cadillac Mountain.

Thunder hole in Maine

Next, we drove to Thunder Hole in Acadia to take more pictures. It got its name from how the water sounds when it splashes against the rocks. I’m glad we stopped here, especially because it makes for a great photo op, but if you’re really short on time, this spot would be okay to skip.

Four girls at Jordan pond house standing in front of the pond

Jordan Pond House is the perfect spot for hikers and non-hikers, alike. For the outdoorsy, there’s a trail that loops around the pond, or you can hike South Bubble Mountain down to Jordan’s Pond Loop (see the AllTrails app for more guidance). On the other hand, if you’d prefer to get a few pictures, meander around, and do a little browsing in the gift shop, you can do just that at Jordan Pond House, too! I would advise at least walking down to the pond because the views are beautiful—it’s not a long walk at all.

Note: The parking at these last three locations I mentioned fill up quickly, so be sure to arrive early.

Town of Bar Harbor

We spent plenty of time in Bar Harbor and had the BEST food I’ve ever eaten—my blog post on the best restaurants in New England is coming soon!

I fell head over heels in love with the village of Bar Harbor. There were lots of shops, and a few of my favorites were the Acadia Country Store and Sherman’s Bookstore. I got plenty of souvenirs. Near the water, there’s a Shore Path, which is easy and scenic and worth the walk, in my opinion.

Bar Harbor is so very special, and I definitely want to go back!

hiking trail behind the Acadia Inn

Remember how I told you we stayed at the Acadia Inn? Let’s go back to that, and I’ll tell you how much I loved it! We stayed here for two nights, and it was easily my favorite place we stayed because it felt homey, the rooms were nice, and the staff was so very kind. (Don’t even get me started on how good the complimentary breakfast was.) Plus, it’s only a few minutes to Bar Harbor, AND Acadia National Park is literally in its backyard.

Creek and trees behind the Acadia Inn in Maine

Mom, Dad, and I had some free time in the afternoon, so we decided to hike the trail behind the inn. We walked the Duck Brook Path, which takes you to the Acadia National Park Carriage Road system where you can hike bigger trails. The Duck Brook Path was a scenic walk/easy hike. We saw vibrant colors on the trees, a creek, a beautiful bridge, and even a waterfall.

Don’t miss the best spots in New England! Get my FREE map here!

Day 3 – Freeport and Portland, Maine

three girls in front of LL bean boot in freeport, maine

On day three, we drove down to L.L. Bean in Freeport, Maine. If you’re a shopper, you’ll want to schedule time to drop by and explore the store. Several people in our group remarked that they’ve “never seen so many coats in their life,” and I had to agree.

four girls in front of Maine mural outside of LL Bean

At this point in the trip, my suitcase was already bursting at the seams (and looked nine months pregnant, my sister joked), so I couldn’t actually buy anything from the store. But that’s where the Internet saved me again—or hurt me since I spent money, depends on how you look at it. In the L.L. Bean store, I found a fleece pullover and rain jacket and tried it on to see how it looked and gauge my size. Then I just tapped a few buttons to make an online order and voila! New clothes secured.

For lunch, we spent some time in Portland, Maine. Consequently, Portland, Oregon was named after this city in Maine. It’s modern and is a very fast-growing city, especially for young families because there’s a lot to do, and it’s safe. I can’t wait to share about the pizza place where we ate. Makes my mouth water just thinking about it.

mom and daughter looking into a mirror in portland, maine

Portland has lots of great shopping and is a waterfront town, so there’s places for photo-ops and lots of things to do. One activity tourists enjoy in Portland is the boat tours. 

We finished the day by driving to North Conway, New Hampshire.

Day 4 – Conway, New Hampshire

The fall foliage against the backdrop of the White Mountains in New Hampshire is beautiful!

scenic railroad in conway, new hampshire

In Conway, New Hampshire, we rode the Scenic Railroad. Be sure to reserve tickets in advance because they sell out quickly. We chose the 55-minute excursion, but I’d definitely recommend a longer one. I’ve heard the longer rides have better scenery and are more memorable.

town of conway, new hampshire

After you finish your excursion, be sure to walk around town. We enjoyed visiting Zeb’s Country Store and taking pictures in front of all the cute shops before leaving.

girl looking at lower falls on kancamagus highway

One of my FAVORITE drives and scenic photo stops was the Kancamagus Highway (or “The Kanc,” as locals call it). It was stunning, and our heads were on a swivel trying to take in all the autumn colors and rushing rivers. 

We made three stops along the Kancamagus Highway—Albany Covered Bridge, Lower Falls, and Wangan Overlook.

family standing in front of albany covered bridge in New Hampshire

The Albany Covered Bridge had the picturesque New England covered bridge that everyone wants to capture.

lower falls on kancamagus highway

Our stop at Lower Falls let us get up close and personal with nature. We walked down to the river and took lots of pictures on the rocks. I cannot tell you how surreal it was to see the rushing water and the autumn leaves with the New Hampshire White Mountains in the background. We recorded a video of it, but, of course, it doesn’t compare to seeing it in person.

Last, we drove up in the mountains and went to Wangan Overlook. It overlooks the mountains below and gives you a bird’s eye view of New Hampshire. Definitely worth the chilly air and wind that comes along with being up so high.

Looking to bring fall to where you live? Need good soup recipes, fall music, and book recommendations? Be sure to also read my post: Cute Fall Bucket List Ideas | Recipes, Books, Clothes

Day 5 – Woodstock, Vermont

madelyn victoria in Woodstock, Vermont

Since Woodstock, Vermont is dubbed “the prettiest small town in America,” we were excited to explore it. Vermont is the third least populated state in the U.S., but it gets quite a few visitors during the fall. And believe what you’ve heard: Woodstock really is an idyllic small town!

Three sisters in Woodstock, Vermont

After we ordered the obligatory maple crème latte at the Mon Verte Cafe, we went to Gillingham’s General Store. This store was fun to browse because it has to fulfill the needs of both tourists and locals. We saw they have souvenirs and travel necessities for the tourists, and also groceries and cow manure for locals. 🙂

shelves of Vermont maple syrup in country store

I was so excited to get my long-anticipated maple syrup here. Two days after we got home, I made pumpkin pancakes and sampled my syrup, and it was incredible. Definitely worth the wait, for sure, and I will be rationing it until I can get some more…

wooden wagon at Billings Farm in Vermont

Vermont is known for its farms, so we made a excursion to Billings Farm. If you have the opportunity to visit, you definitely should!

Museum at Billings Farm in Vermont

Not only was seeing the beautiful countryside and farm animals fun, but we enjoyed learning about the daily operations on the farm. The farm also has a museum that shows early farm life and how it’s transformed and modernized over the years.

maple ice cream at billings farm in vermont

The farm is quite large, which means there’s lots to explore. Besides the museum, they also have an ice cream shop, much to our excitement. I tried the maple ice cream (because when in Vermont…) and loved it.

Before we left, we saw a calf that was born the day before we visited. I wish I had a picture, but the little guy’s name was “Jericho”—isn’t that adorable?

Quechee Gorge in Vermont

If you’re a nature lover or appreciate beautiful scenery, Quechee Gorge is another good place to stop. There’s a bridge overlooking Quechee Gorge where you can take pictures, or if you want to get up close and personal, there’s trail behind the visitor center that leads down to the gorge. Dad and I opted for the latter, but the steep walk back up had us both panting hard. It was worth it for the views, though!

That afternoon, we went to the Vermont Country Store. Not only is it home to the infamous “Kissing Bridge,” but it also has lots of trinkets, souvenirs, home décor, and baked goods inside. A lot of people in our group said they often order from the Vermont Country Store magazine.

Before we settled in for the night, some of our group walked around Brattleboro, Vermont. It’s an artsy town, known for its urban art, food, and shopping.

I loved my time in Vermont; I just wish it had been longer! I definitely would have liked to go to Stowe, Vermont, especially after seeing all the beautiful pictures and hearing the food recommendations. Next time, for sure!

One person in our tour group also suggested going to Burlington, Vermont if we were able to visit New England again (I’m manifesting that this happens next year…).

Day 6 – Stockbridge, Concord, and Lexington, Massachusetts:

red lion inn in stockbridge, massachusetts

Several people in our group commented that Stockbridge, Massachusetts was their favorite town we traveled to. It has the picturesque, Hallmark-y New England town vibes that you might imagine. The downtown area was even decorated with fall and Halloween decorations, which added to the ambiance even more.

Stockbridge has a historical past, as it’s the town Norman Rockwell often painted in his pieces and was also where he lived. Before we arrived, we watched a documentary about Rockwell’s life and career, which gave me even more of an appreciation for his work. I definitely recommend watching it—even if you don’t stop in Stockbridge. Rockwell created art that evokes an emotional response, and I’m sure you’re familiar with more of his work than you might think.

The downtown buildings in Stockbridge are the sight of Rockwell’s famous painting, “Stockbridge Main Street at Christmas.” It captures the holiday cheer, hustle and bustle, and excitement perfectly, and it invites you to live in the memories of Christmases gone by.  

The Red Lion Inn in Stockbridge is a building that also has direct ties to Rockwell. He used to sit out on the front porch with his friends every week, and several of his paintings hang inside to commemorate his time there.

Outside of Norman Rockwell Museum in Massachusetts

Close to the downtown area is the Norman Rockwell Museum, and I am so glad this part was included in our trip! Seeing Rockwell’s paintings up close and reading about them made them come alive. He captured the lives of real people and daily life in his paintings so well, and his attention to detail is amazing (for example, look at the reflections in the water glasses of the piece, “Freedom from Want” aka the “Thanksgiving Picture”).

We had the unique opportunity to tour his studio, which our tour guide told us was literally cut in several half years ago so they could move it to where it now sits on the property. On the day they moved it, school was even canceled so the children could watch.

three sisters standing on the old north bridge

To continue the theme of history, we drove to the Old North Bridge in Concord, Massachusetts, where the “shot heard round the world” was fired. (Fun fact: the locals pronounce Concord like “Kahn-Kurd.”)

We had a very lively tour guide who told the story of how the American Revolution started, and, of course, we took pictures on the Old North Bridge and by the Minutemen Statue. Did anyone else watch the Schoolhouse Rock video, “The Shot Heard Round the World” when they were little? It played on repeat in my head the entire day.

Off to the Lexington Battle Green we went, which is where the first drop of blood was shed in the American Revolution.

Though there are places to park, if you’re pressed for time, I’d suggest just driving by.

Day 7 – Boston, Massachusetts

two girls in boston massachusetts

If you’re in New England, you, of course, must go to Boston, Massachusetts! I really enjoyed our time there, and wish we could’ve stayed even longer.

We took a history tour and walked along the “Freedom Trail,” which is a 2.5 mile walk that passes by 17 locations significant to the history of the United States. Most of the walk is marked with a brick pathway.

One of my favorite parts about Boston is the juxtaposition of old and new. On one corner, there might be a building that’s been around for hundreds of years. Then across the street, there might be a skyscraper that was recently built. The contrast is so evident, but there’s room for both in Boston.

My parents enjoyed the historical aspects of the city, for sure, but they weren’t a fan of the crowds. While I’m not usually either, I didn’t find it too overwhelming because it’s just the way of life there.

grasshopper on top of faneuil hall

For lunch, we ate at Quincy Market and shopped afterwards. Quincy Market is the oldest dining hall in America and has open vendors. Though it’s especially busy at lunch, the lines move quickly. Across from one of the entrances at Quincy Market, there’s a building called Faneuil Hall, where a grasshopper weathervane perches on top. Our tour guide explained that this weathervane was a tool used to detect potential British spies hundreds of years ago. If an individual couldn’t identify what rested atop Faneuil Hall, then they were viewed with suspicion.

clock in front of the best of boston giftshop

There’s also lots of shopping, and one of our favorite shops was Best of Boston. We all got some sort of souvenir, whether it was a sweatshirt, magnet, ornament, or even a stuffed animal.

At last, it was time for us to bid Boston “goodbye,” and head to the airport for our flight home.

My best tips for traveling to New England in the fall

Bridge in Woodstock Vermont

Dress in layers and check the weather often. The weather changes all the time!

There are lots of cities with the same names (for example, there’s a Woodstock, VT and a Woodstock, NH). Make sure you type in the state in the Maps app.

If you’re planning to fly, leave room for souvenirs in your suitcase. I wish I had room to bring back some Maine blueberry jam…

I’ll talk more about this in my post about the best places to eat in New England, but just know you should plan to go to restaurants early on the weekend. Reservations or waitlists are a good idea, too.

Boston has crazy bad traffic, especially during rush hour. Plan accordingly.

Most of the time, there are lots of public restrooms available for tourists. Just search it on your Maps app.

Is Going to New England in the Fall Really Worth It?

sisters at Billings Farm in Vermont

Exploring New England in the fall is 100% worth it. Pictures don’t capture the beauty of the trees and towns, and words don’t adequately express how awesome the people are. I know this sounds corny, but experiencing fall in New England is magical.

Download my FREE map of the best leaf peeping spots, places to eat, and activities to do in New England!

Next week, I’ll share the 12 Best Restaurants in New England! I’m not exaggerating when I say that I had some of the best meals of my life on our trip. (I’m a wannabe-foodie, for sure.)

I hope this ultimate 7 day itinerary to New England in the fall helps you plan your own trip! Have you ever been before? Leave me a comment sharing your favorite place you’ve visited or a place where you’d like to go!

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