Steal Our Boston & Maine Fall Break Itinerary

A family-friendly fall getaway through Boston and coastal Maine- what we did, where we ate, and the stops we’d absolutely make again.

DAY ONE

Classic Boston in the Fall

We started our first day with a private tour of Fenway Park, which ended up being such a fun way to kick off the trip- even if you don’t plan on catching a Red Sox game. Our oldest has a big goal of visiting all of the MLB stadiums and we planned the trip around getting him to Fenway. From there, we headed toward the Public Garden and Boston Common before spending the afternoon wandering Beacon Hill. It was one of those days where simply walking from place to place was part of the overall experience, especially with all the row homes dressed up for fall. The East Coast fall weather was lovely.

From Fenway, we made our way to Boston Public Garden and Boston Common. We stopped to see the Make Way for Ducklings statues- the sweetest little stop with kids- and wandered through Boston Common, America’s oldest public park. (Pro tip: If your kids know Make Way for Ducklings, read the book together before the trip. It makes finding the statues a little more magical. ) Both of these are easy to explore together and start the trip off in a nicer slower-paced way.

My favorite part of the day was wondering around the Beacon Hill neighborhood. The historic row houses are always beautiful, but in the fall they really show off. Pumpkins spilling down stoops, window boxes filled with mums, and little neighborhood shops tucked along the brick sidewalks. Give yourself time here without much of agenda.

Definitely make time for a stop at Beacon Hill Books & Cafe. It’s every bit as charming as you’d expect, but what made it extra fun for us was stumbling into a children’s book reading and signing while we were there. Check their calendar before your trip to see what they have going on!

We ended our first day with dinner at MIDA on Tremont Street. After a full day exploring, it was the perfect spot to settle in for a really great Italian dinner. It felt elevated enough for the adults, but comfortable for dinner with kids. The sweet spot for us when we travel.

MIDA

782 Tremont Street

DAY TWO

A Day Trip To Kennebunkport, Maine

If you want to feel like you’ve stepped straight into a fall Hallmark movie, go to Kennebunkport in October. The entire town felt almost too charming to even be real. We made a full day trip of it from Boston, with a few stops along the way, and we all can’t wait to get back to Maine. We woke up really early and made a pit stop in Portsmouth, New Hampshire to have breakfast and coffee at Elephantine Bakery.

From Portsmouth, we continued north to Kennebunkport and as soon as we stepped out it felt like quintessential New England in the fall. We wandered through the town, popped into shops and just took it all in.

If you take one piece of advice from this itinerary, let it be this: SKIP the overhyped places like Clam Shack and GO TO MABEL’S. We somehow turned this trip into an unofficial clam chowder taste test and tried six different spots between Boston and Maine. This was hands down our favorite. Get the chowder!

After Mabel’s, we drove out toward the coast to explore the rocks and see the Bush family compound. The rocky Maine coastline is beautiful, and seeing Walker’s Point along the way was a fun addition to our itinerary.

From there, we headed to Nubble Lighthouse. This ended up being another favorite stop, especially for the boys, who loved climbing around and exploring the rocks. On the way back to Boston , we stopped in York, Maine, and let the kids run down to the beach and put their feet in the ocean. It was simple, but one of those super special moments. One thing I’d do differently: bring an extra set of clothes for everyone. “Just putting your feet in” can very quickly turn into getting a lot wetter than planned.

If you steal this day: don’t rush it. Easily one of my favorite days as a family. It felt like a giant deep breath.

DAY THREE

Apple Picking & A Slow Afternoon in Back Bay

For the third day, we traded the city for a truly quintessential New England fall morning and drove out to Smolak Farms. We picked apples, ate warm apple cider donuts, visited the petting zoo and let the kids play on the playground. There was enough to keep everyone entertained there without too much of a plan. The apple cider donuts alone were worth the drive.

After the farm, we headed back into Boston for lunch at Satlie Girl. It’s chic, delicious, elevated, but still doable as a family. They had all kinds of tinned fish and we all went outside of our comfort zone to try new things. (Lots of more regular menu items as well, of course.) Definitely make a reservation.

After lunch, we spent the late afternoon in Back Bay. Even more admiring of the picture-perfect fall dressed row homeds and stopped at a couple of playgrounds along the way for the kids to play.

One thing we always love to do when we travel is giving our kids opportunities to actually interact with local kids. Some of their favorite memories from our trips have come from simple things like finding a playground and joining in on a game that’s already happening.

By the time we made it back to the hotel, everyone was done- in the best way. Instead of trying to squeeze in one more dinner reservation, we all put on robes, ordered room service and got cozy for the night.

I love ending travel days like this because it reinforces something I fits our whole travel mantra with kids, you don’t have to fill every second of the day. Magic happens in the space.

DAY FOUR: Books, Boston History & A Fancy Farewell

The last day unintentionally ended up with a bit of a learning-and-history theme- and it was the perfect way to wrap up the trip.

We started our morning at Boston Public Library, which is worth visiting whether you are visiting with kids or not. Beautiful and the kids section is huge!

As luck would have it, my sister’s Boston trip overlapped with ours, so we met up with her afterward. She’s a history teacher, which made a Boston walking tour feel especially fitting. It was fun for the kids to actually learn some of the stories behind the places we’d been seeing all week- and having their aunt there made it even better.

We like to end every trip with a fancy dinner. I get the kids dressed up and we talk about the “pit and peak” of everyones trip. One of my favorite traditions.

I hope I’ve convinced you to add the East Coast to your fall break travel list. It’s truly special.