The Ultimate New England Family Weekend Itinerary: Maine, Salem & Boston
A Cozy New England Fall Road Trip: Lighthouses, Lobster Rolls & Halloween Magic | 10.31.26
From coastal Maine and charming seaside towns to Boston adventures and a little Halloween magic, this was the perfect New England getaway with my nieces.
My nieces were visiting New England for the very first time, and I knew I wanted to show them a little bit of everything. Naturally, that meant a trip to Maine! Between adorable coastal towns, lighthouse adventures, delicious food, and a little Halloween fun, we packed so much into one unforgettable weekend.
Day 1: Coastal Maine Adventures
As soon as the girls landed, we kicked off our adventure with coffee at Adrianna’s in Winthrop before stretching our legs with a walk along Winthrop Beach. I also brought along some donuts from Blackbird Doughnuts for the road - pumpkin and apple cider donuts, because what would a New England fall weekend be without them?
After our morning stop, we made the hour-and-a-half drive to Ogunquit.
Our first stop was lunch at the adorable Barnacle Billy’s, where we shared appetizers and a variety of seafood. It was the perfect little seaside lunch overlooking Perkins Cove!
Afterward, we wandered around town, popped into the cute souvenir shops, took photos on the bridge, and watched the boats come and go. We even walked a little way along the beautiful Marginal Way, taking in all the coastal views.
Then it was back in the car and off to Portland!
We headed straight to Spring Point Ledge Lighthouse, which ended up being one of the girls’ favorite stops of the entire weekend. They absolutely loved hopping from rock to rock! It was a little intimidating at first, but with a hand to hold, they made their way all the way around the lighthouse.
By the end of the trip, they told me this was one of their favorite parts of the vacation. It was such a sweet reminder that sometimes the simplest adventures make the best memories.
We wrapped up our first day with Otto’s pizza, enjoyed back in our hotel room after a full day of exploring. Nothing better than a cozy pizza night after a busy day!
Day 2: Portland, Lighthouses & Halloween Magic
We started our second morning at Tandem Coffee and Bakery. I had been searching for cute coffee spots nearby and came across this one with amazing reviews. But honestly, it was even cuter and better than we expected!
There was quite a line when we arrived, but I can confidently say it was worth the wait. They had delicious biscuits, breakfast sandwiches, and maple coffee. We grabbed everything and enjoyed breakfast at the picnic tables right outside the cafe.
After breakfast, we hopped aboard a cute little train ride along the coast. The girls absolutely loved it! We spent some time wandering around the charming town afterward before wrapping up our Portland adventure.
Of course, we couldn't leave without visiting Portland Head Light. We took in the beautiful lighthouse views and grabbed some lobster rolls and grilled cheese before hitting the road.
On our way back toward Boston, we made a spontaneous stop in Salem to walk around the magical little “Halloweentown.” Since it was October, the town was full of Halloween decorations, festive activities, and all the spooky-season excitement you could imagine. It was such a fun little detour!
Once we made it back to the hotel, the girls got to enjoy some time swimming in the pool before another busy day ahead.
Day 3: Boston Adventures
We kicked off our final day with a visit to the New England Aquarium. We watched a movie, saw the seals, and explored all the fun exhibits. It was such a great way to spend the morning with the kids!
Afterward, we wandered around Boston and made sure to stop at the famous “cop slide” - because obviously, you can't visit Boston with little ones without making a stop there! This was another favorite stop for the kiddos!
We continued exploring the city, went on a cutie carousel ride and eventually stopped at a brewery overlooking Faneuil Hall for a little break.
That evening, we headed to the North End for dinner. And, of course, no trip to the North End would be complete without a stop at Mike’s Pastry afterward!
While the girls were winding down, my sister and I grabbed a drink at 1928 in Beacon Hill before heading out on a walking ghost tour. It was such a fun way to end the weekend and enjoy a little grown-up Halloween magic of our own.
A New England Weekend to Remember
This weekend was such a wonderful reminder of how much New England has to offer, especially in the fall. From Maine’s beautiful coastline and charming seaside towns to Salem’s Halloween magic and Boston’s iconic sights, there was something for everyone.
The girls got to experience so many new things, and seeing New England through their eyes made it even more special.
If you're looking for a fun weekend itinerary with little ones, this is one I would absolutely recommend. Just be prepared to eat lots of seafood, walk plenty of miles, and make some unforgettable memories along the way!
With Love,
LC