Traveling to New England had honestly not crossed my mind much until I started seeing photos and videos circulating across Instagram of these absolutely stunning colors and views of New England in the Fall. I had heard about the leaves changing but just did not realize how spectacular the views could be. One of my favorite bloggers spent a few weeks there last year and shared so much about the area, that I knew I wanted to plan a trip to that region. So along came Fall of this year and we were able to score some cheap tickets to Boston and the fall foliage trip with a toddler in tow came to life!

We absolutely love traveling with our daughter, Mila. We’ve taken her to Hawaii, Colorado, NYC, and Portugal now and she is a travel lover just like her parents, for sure. When I saw the activities to do in New England around this time of year, I was honestly so excited to bring Mila, because it sounded like the perfect trip to do with a toddler. Apple picking, hay rides, dairy farms, sweet treats? What’s not to like, right? But we’ve learned from our previous trips, that timing is everything with a toddler and it does take a special set of skills to plan the right trip for a toddler to limit meltdowns (not avoid altogether, because, let’s face it, they will happen), build in some nap time, and maximize our vacation time as well.

WIth all that being said … I have to give ample credit to Helene Sula. Her blog page on Fall foliage in New England is honestly extensive and has SO much useful info. I found a lot of our planned stops through there, but made a few adaptations and additions to work for a more family friendly approach.

Before anything else, I recommend to check the leaf peeping tracker. We went at the start of the leaves changing, and while it was still gorgeous, I think I would have preferred to have gone around the first week of October for better foliage. We did our trip in 4-5 days, but if you afford at least one week, I would definitely do it! There was so much to see. Plan accordingly!

A note on packing – bring lots of light layers! The mornings and evenings are definitely chilly for us Texans. Here’s what I brought along for myself.

The Itinerary:

Day 1: Dallas –> Boston –> Andover

Arrive in Boston. I recommend trying to get an early morning/afternoon flight. We left Dallas around noon and arrived at 4:30 PM. Get your rental car (this may take a while, we had super long lines). I recommend to take advantage of being in Boston and grab a quick bite for dinner. We were running a little late from the rental car line but grabbed a pizza at Upper Crust in the Beacon Hill area. We were hoping to walk around a little in the Boston Common, but had to skip because of time. We made our way to Andover for the night to get out of the city and avoid some traffic for the next morning.

Day 2: Andover –> Amesbury –> Portsmouth –> Conway –> Lincoln

We knew that we wanted to do some apple picking and stumbled on great reviews for Cider Hill Farm in nearby Amesbury. We bought tickets online (was about $12 to pick half a peck for two people, kids under 3 are essentially free). This was SO fun! Read more about the farm below in the “stops” section, but this was probably our TOP outing. After coffee and apple cider donuts for breakfast we headed to Portsmouth for lunch, about a 40 minute drive. Parking was easy to find and Portsmouth was such a cute town to wander, right on the coast. We had some excellent lobster rolls at Surf Seafood and bought a few trinkets in town before loading back up to head to Conway. Drive time was about 2 hours, so we planned this to time with Mila’s nap, usually around 1 PM.

We arrived in Conway around 3 ish and walked around a little and got a coffee at Frontside Coffee Roasters. We had considered doing the Conway scenic railroad there, but the times just didn’t work out with our schedule and we thought Mila was still a bit too young to enjoy it. I think it would be great for slightly older kids though.

We continued onto the Lincoln via the Kancamagus highway, which we heard was filled with amazing views. We made a few stops — the Lower Falls, the Rocky Gorge Scenic Area, and Sabbaday Falls. All had ample parking and short walks from the freeway, great for Mila. Sabbaday Falls was probably our favorite stop!

We arrived in Lincoln around 5 PM and searched for dinner. We had planned on burgers at Black Mtn Burger Co, but there was a 2 hour wait,  so we ended up at a local brewery, One Love Brewery. The beer was good and they had a nice outdoor seating area, but food was mediocre.

Day 3: Lincoln –> Montpelier –> Stowe

The nice part about staying in Lincoln was easy access to the Franconia Notch State Park. If we had more time, I would have spent longer here, but we just stopped at the Basin — it was a quick hike from the highway and ideal for a toddler attention span.

After this, we continued onto Stowe, making a pit stop in Montpelier at the Bragg Farm Sugar House to sample their maple creemees and got a few maple treats to take home. They also have some goats outside and overall beautiful area for a quick break.

Our first stop in Stowe was for lunch – we ate at Doc Pond’s — limited menu but VERY good and they do have a kid’s menu. We were nearing Mila’s nap time now, so we loaded her into the stroller with her sound machine and made our way to the recreational bike path that winds around Stowe. It was so peaceful and quiet, and easy to access from Doc Pond’s — just walk towards the bike shop and you’ll see the signs guiding you. It was about a half mile walk to the main part of town. We explored a little while Mila napped and got a coffee at Black Cap Coffee & Beer.

After the woke up, we headed to our hotel — the Lodge at Spruce Peak for the rest of the afternoon. We took the Over Easy gondola with Mila (free) which she thought was so fun. You can take the upper gondola to the top of the peak, but it was $35/pp and stopped running around 4:30 PM. We explored the hotel grounds – they have a little “enchanted playground” which was super cute, and a nice garden, as well as an outdoor heated pool. We had dinner at the hotel to keep things easy.

Day 4: Stowe –> Waterbury –> Woodstock –> Boston

We woke up early and explored Smuggler’s Notch State Park. We stopped at the Barnes Camp Visitor Center, which had a great paved boardwalk for a short hike. Next, we made our way towards Woodstock, stopping in Waterbury to sample the famous Cold Hollow Cider Donuts (worth the stop). This is also where the Ben and Jerry’s headquarters is, and we heard the tour is super fun for kids, but they are closed Sunday/Monday, so unfortunately we missed out on that!

In Woodstock, we made our way to the Billing’s Dairy Farm. This was such a great stop for kids. You can actually get up close with the cows, even pet them if you want. They also have several other animals like goats, sheep, chickens, etc. We had a simple lunch with cheese and yogurt made with their milk. They also had some additional local snack boxes with salami, crackers, and fruit as well.

We drove around Woodstock a little, saw the Sleepy Hollow Farm that is very picturesque, and grabbed another creemee in the downtown area at Woodstock Scoops (this time a maple/pumpkin swirl). Mila was very ready for her nap so we decided to head towards Boston shortly after. This was about a 2 hour drive, which allowed her to get another good nap in. Woodstock was such a beautiful town — would love to spend more time here next time, there were so many cute inns we saw!

We drove directly to the rental car drop off and dropped our car off early to avoid having an extra step before our early morning flight. We booked the Hyatt Regency Boston Harbor, which conveniently has a free shuttle that picks up from the rental car area, so we hopped on that afterwards. What’s especially cool is that you can hop on a water taxi right in front of the hotel and get to the other side of Boston in about 10  minutes! The hotel can give you tickets (about $15/one way). Drop off was at Long Wharf, which was a short walk to the North End, where we had a nice little Italian dinner.

Day 5: Boston –> Dallas

We took the shuttle from the Hyatt to the airport — which was only about a 5 minute drive, so this helped considering our 8 AM flight home. Sometimes sucks to lose a whole day to traveling, but we liked the timing. We were able to get home just in time for Mila’s nap.

Where We Stayed:

We travel with points a lot and used them to book all of our hotels this trip. We used a combination of Hyatt points, IHG points, and American Express points to book. There are a ton of super cute inns and B&Bs in the area, but most required a minimum stay of two nights, which we couldn’t do with our itinerary. Also, most have small rooms and close quarters, which is not great with a toddler. These hotels below were all able to either provide a roll away crib or pack n play, or we booked two queen beds and made a little pillow fort for Mila.

Holiday Inn Express Andover

Holiday Inn Express Lincoln

The Lodge at Spruce Peak **

Hyatt Regency Boston Harbor **

**Highly recommend both of these hotels. Beautiful properties with great locations.

What We Ate:

• Upper Crust Pizza, Boston
• Coffee, cider donuts at Cider Hill Farm, Amesbury
• Lobster Rolls, Clam Chowder, Fried Green Beans at Surf Seafood, Portsmouth
• Pumpkin Spice Lattes at Frontside Coffee Roasters, North Conway
• Maple/Chocolate Creemees at Bragg Maple House, Montpelier
• Tomato Soup, Burger, Ham and Cheese Sandwich at Doc Pond’s, Stowe
• Uni Pasta, Seared Fish at Tipsy Trout, Stowe
• Cider Donuts at Cold Hollow Cider Mill, Waterbury
• Pumpkin/Maple Creemee at Woodstock Scoops , Woodstock
• Bolognese Pasta, Chicken Milanese at Al Dente, Boston

Activities:

• Cider Hill Farm: Apple picking, hay rides, animals, price varies depending on how much apple picking you want to do, but starts at $12/couple
• Billing’s Dairy Farm: Museum, Farm Animals, Sampling of milk, yogurt, cheeses; $17/adult, children under 4 are free
• Kancamagus Highway Drive: Free
• Franconia Notch State Park: May have to pay depending where you enter/what you do. Basin area was free.
• Smuggler’s Notch State Park: Free
• Bragg Maple Farm: Sampling maple syrup
• Over Easy Gondola: Short Gondola ride with nice views, free
• Recreational Path in Stowe: Free
• Water Taxi Ride in Boston: $15/pp one way

Honorable Mentions:

• Conway Scenic Railroad
• Ben and Jerry’s ($6/adult, $1/child for tickets)

Hope this information is useful! We cannot recommend taking a fall foliage trip with a toddler enough. There were so many family friendly activities, gorgeous views, amazing food, no complaints from any of us! The memories will be with us forever. We are just hoping to go again another year a few weeks later to catch even more of the beautiful leaves changing colors.