This past weekend, we took a fun family friendly road trip from Boston to Maine. Weaving through historic streets and coastal charm, this journey was filled with laughter and constant wonderment at the beauty of our country. Here’s a peek at our three-day itinerary filled with New England’s best!

We were lucky to be there when the leaves were very bright. If you get lucky enough, keep your eyes on the trees while you drive. The colors are so magnificent. If you want to plan your trip around the fall leaves, there are several sites you can use to help you plan. This is one of them.

Friday: Arrival in Boston → Drive to Portland

We landed in Boston with excitement bubbling over, picked up our rental car, and started the adventure with a hearty lunch at Bell in Hand Tavern. The tavern, a cornerstone of Boston history, sits proudly near Faneuil Hall, offering good food and a perfect introduction to the city’s timeless atmosphere. I would definitely recommend the hot lobster roll, which Eddie and I first tried a couple years ago.

Before setting off for Portland, we wandered through Quincy Market, soaking in its bustling energy. While Boston was tempting us to stay longer, we hit the road, knowing the coastal beauty of Maine was calling.

Our first stop was Portsmouth, NH—a charming little town that’s easy to fall in love with. We stretched our legs at Market Square and strolled through Prescott Park, taking in the crisp fall air. We arrived in Portland after dark. We were so tired that we checked into our hotel* but several spots were recommended multiple times for dinner – Eventide Oyster Co. or Central Provisions, both known for their fresh seafood and cozy atmosphere.

Saturday: Exploring Portland and Kennebunkport

Saturday morning, we started the day with a hearty breakfast at The Porthole, nestled right by the waterfront. After filling up, we wandered through Portland’s Old Port district. The cobblestone streets, unique boutiques, and the waterfront views kept the kids entertained, while we took our time savoring a stop at Holy Donut—because you can’t leave Portland without trying one!

Next on the list: the breathtaking Portland Head Light. We headed to Fort Williams Park to take in the striking lighthouse and its rugged coastal backdrop. It’s one of those places where you can feel the majesty of nature, and the kids loved exploring the park’s open spaces and the Cliff Walk.

In the afternoon, we drove south to Kennebunkport, starting with a peaceful stroll through Dock Square. It’s a quaint, postcard-perfect town. We had lunch at Federal Jack’s. Afterward, we checked out the local shops and made a coffee stop at Dock Square Coffee House to refuel.

We also drove by Walker’s Point, offering a distant view of the Bush family estate, a piece of American history perched on the cliffs. Our coastal exploration ended at Mothers Beach, where the kids could run free. Though Snug Harbor Farm was closed, it still made for a beautiful photo stop!

The evening was spent back in Old Port at Portland Lobster Company, where live music played and we sipped on hot mulled wine as the kids enjoyed the last bit of their day. Dinner was at Off-Track Pizza, where kid-friendly pizzas and the relaxed vibe were a perfect close.

Sunday: Drive Back to Boston

We started Sunday morning with a visit to St. Margaret Church in Old Orchard Beach for Mass.

Afterward, we made our way to Ogunquit, where a scenic walk along Marginal Way offered stunning ocean views and some of the most peaceful moments of the weekend. Perkins Cove was the next stop, and a lobster roll at Barnacle Billy’s did not disappoint. For a sweet ending, we stopped by Big Daddy’s Ice Cream before heading out.

As we made our way back, we took a detour to Applecrest Farm Orchards in New Hampshire for some quintessential fall fun. The orchard was buzzing with families, and the kids (and adults) loved the fresh apples and cider donuts.

Back in Boston, we checked into the Hyatt Regency and set out to explore the city on foot. We walked through the iconic Boston Common and followed the Freedom Trail, a perfect way to introduce the kids to history while enjoying a leisurely walk.

Dinner at the historic Union Oyster House capped off the day.  Because this is one of the oldest restaurants in the country, it is a popular spot and on all the must-visit lists. Bust honestly, we didn’t think the food was anything out of this world. Maybe stop in for a drink at the bar and an appetizer, but find somewhere else for dinner.

Monday: Wrapping Up Our Journey

Monday morning, before leaving, we made a few final stops. We visited the Paul Revere House and the North End Church, both filled with the echoes of America’s early days. Then we drove over to the Bunker Hill Memorial, where we walked around the neighborhood, soaking in the significance of the Revolutionary War.

A question I always get after these trips is, “Was it good for kids?” Someone gave me this advice once, and it has always stayed with me and changed how I felt about bringing the kids places with us. Every place in the world has kids. No matter where your destination (barring an adults-only resort/hotel), there will always be a place for kids, because kids exist everywhere. Whether you want to bring your kids along will determine what activities you’re going to do, but you can always find places for them.

But this family friendly road trip from Boston to Maine was definitely filled with awesome moments for the kids, and I’m pretty sure they loved it as much as we did. Caleb’s top moment of the trip was trying a lobster roll for the first time, and Chloe’s was feeding goats!

*Also, I’m not recommending the hotel we stayed at in Portland. It was near the airport, and the location was fine, but the hotel itself left a lot to be desired. Because we planned the trip with pretty short notice, hotel prices were very expensive and very limited. If you plan with more time, I’m positive you can find a great hotel option in Maine. Kennebunkport and Ogunquit were filled with adorable Inns and Bed & Breakfasts.