When we told people we were flying to New England for ten days with a nine-month-old baby, the reactions were almost always the same:
“Wow. You’re brave.”
What we discovered is that traveling with a baby isn’t nearly as difficult as people make it sound. It does require more planning, more snacks, and a willingness to abandon your carefully crafted itinerary at a moment’s notice—but it also slows you down in the best possible ways. We spent more time enjoying the scenery, lingering over coffee, and taking morning walks than we probably would have otherwise. More on my advice for traveling with a baby here.
Over ten days, we explored Boston, coastal Maine, Acadia National Park, the White Mountains of New Hampshire, and Portland. We hiked waterfalls in the rain, watched sunsets from Cadillac Mountain, rode a train into the clouds, and consumed an alarming quantity of pastries.
Here’s how it all unfolded.
Day 1: Arriving in Maine (and Ordering Pizza Instead)
Our adventure began with an evening arrival in Maine and a drive to Ogunquit.
The plan was simple: check into our hotel, stroll along Marginal Way, and enjoy a seafood dinner by the water.
Mother Nature had other ideas.
By the time we arrived, it was absolutely pouring rain. Rather than dragging ourselves—and a tired baby—back out into the weather, we embraced Plan B and ordered takeout from Brickyard Hollow Brewing Company.
Honestly? It was the perfect way to start the trip. Their pizza was creative, delicious, and exactly what we needed after a long travel day.
Day 2: Falling in Love with Boston
The next morning, we were up early and headed to Boston.
We arrived in Cambridge around 9:20 a.m., parked in Harvard’s Holyoke Garage using SpotHero, and started the day with coffee and pastries from Tatte. If your ideal vacation includes excellent baked goods, you’re going to notice a theme throughout this post.
After a fascinating Harvard tour, we browsed the Harvard Shop before driving into downtown Boston.
Lunch was at Hei La Moon in Chinatown, and choosing a restaurant was surprisingly difficult because every block seemed packed with amazing options. Hei La Moon was tasty, and the staff were so friendly with our baby. They even brought him a fortune cookie to try!
From there, we wandered to Brattle Book Shop and then Boston Common.
Of all the places we visited on this trip, Boston Common may have surprised me the most. It’s one of the most beautiful city parks I’ve ever visited, and I’d strongly encourage anyone visiting Boston to spend time there before starting the Freedom Trail.
We followed the Freedom Trail through some of the city’s most iconic historic sites, stopping at the Old State House to collect a stamp in our National Parks Passport. We also wandered through Faneuil Hall and Quincy Market for snacks.
Then came what was essentially a self-guided cannoli tasting tour.
First Modern Pastry- delicious, but my least favorite of the three.
Then Mike’s Pastry- holy (options) cannoli! We picked espresso and limoncello, and they were both amazing.
Then Bova’s- honestly, my favorite overall. You can tell this is the type of place that locals go to. My cannoli was scrumptious, and so was the arancini we bought to balance out all of the sugar we’d been eating!
I’m not saying this was a wise decision. I’m simply saying it happened.
Along the way we visited Paul Revere’s House and Old North Church before walking the waterfront toward the Boston Tea Party Ships & Museum.
We arrived just before closing, with a sleeping baby in the stroller, but I still managed to grab a cup of their famous tea from Abigail’s Tea Room and watch the final reenactment of the day from a nearby bridge.
By the time we left, Boston had completely won us over.
If I could redo this trip, I would absolutely spend more time there—possibly even an overnight stay.
Day 3: Gardens, Trolls, and a Lighthouse Road Trip
Before leaving Ogunquit, we finally got to experience the beautiful coastal scenery we’d missed on arrival.
After breakfast at Cove Café, we walked Marginal Way on a gorgeous Maine morning before heading north. If only I could start every morning with walks like that!
Our first stop was the LL Bean Flagship Store in Freeport. Even if you’re not a big shopper, Freeport is worth a quick stop.
The highlight of the day, however, was the Maine Coastal Botanical Gardens.
Do not skip this place.
We wandered through stunning gardens, searched for all five giant troll sculptures, and explored one of the coolest children’s gardens we’ve ever seen. Any child old enough to walk would absolutely love it.
Before reaching Bar Harbor, we squeezed in one more stop: the Rockland Breakwater Lighthouse.
Walking nearly a mile across the massive granite breakwater feels strangely surreal, almost like you’re walking across an optical illusion stretching into the ocean.
It ended up being one of our favorite unexpected stops of the entire trip!
A mediocre lobster roll dinner later, we finally arrived in Bar Harbor and called it a night.
Day 4: Acadia Plans Change (For the Better)
We started our day early with fantastic coffee and breakfast sandwiches from Mount Dessert Bakery. I would highly recommend a stop (or multiple) stops here during your time in Bar Harbor.
Our original plan was to tackle the famous Beehive Trail first.
Then we looked at the steep iron rungs and cliff edges.
Then we looked at the baby strapped to our backs.
And suddenly the Jordan Pond Loop sounded like a fantastic idea.
We spent the morning circling Jordan Pond and added one of the Bubble Mountains to our hike. The trail offered a perfect mix of rock scrambling, lake views, and peaceful boardwalk sections.
Afterward, we stopped by Jordan Pond House and grabbed their famous popovers from the outdoor popover bar. The indoor wait was over an hour, but the popovers were absolutely worth the stop.
The afternoon was spent wandering the charming streets of Bar Harbor before enjoying dinner and margaritas at Side Street Café and ice cream from Mount Desert Island Ice Cream (try a weird seasonal flavor, even if it seems odd for ice cream…you’ll thank me later!).
That evening, we drove up Cadillac Mountain for sunset.
Or at least we attempted to.
The summit was freezing, incredibly windy, and far colder than we expected for June. We had not brought enough layers and quickly learned an important lesson:
Always assume a mountain summit will be colder than you think.
We left determined to try again.
Day 5: Acadia Redemption
Our second full day in Acadia started at Sand Beach.
We hiked Great Head Trail, spent time exploring the beach, and followed Ocean Path to Thunder Hole.
This combination ended up being one of our favorite stretches of Acadia. The views are spectacular, and Ocean Path is incredibly accessible—even with a stroller in many sections.
After lunch at the Thirsty Whale Tavern and a caffeine stop at Choco-Latte Café, we drove to the quieter side of Mount Desert Island to see Bass Harbor Head Light.
Compared to the crowds elsewhere in Acadia, this area felt wonderfully peaceful.
That evening we prepared properly for Cadillac Mountain Round Two.
Armed with extra layers and takeout pizza from Pizzeria 131, we parked in the west lot and enjoyed what may have been the most scenic pizza dinner of our lives.
As the sun slowly disappeared into the harbor below, we finally got the sunset experience we’d been hoping for.
Day 6: From Acadia to the White Mountains
After breakfast at Jeannie’s Great Maine Breakfast, we began the drive toward New Hampshire.
As lifelong readers and Stephen King fans, we couldn’t resist stopping in Bangor to see Stephen King’s former home and the giant Paul Bunyan statue.
We also made a detour to Maine Wildlife Park.
Unfortunately, this was probably the most underwhelming stop of the trip and one I would skip if planning the itinerary again. We loved their mission of keeping wildlife wild and only keeping rescues in the park, but we picked the wrong time of day to visit (hottest part of the afternoon) and unfortunately saw very little wildlife at all.
By evening we arrived at our riverside Airbnb in Jackson, New Hampshire, unpacked, and settled in.
Day 7: Waterfalls and Hidden Gems
Rain greeted us again the next morning.
Fortunately, waterfalls and rainy weather go together beautifully.
After breakfast from Local Grocer (yummy sandwiches, smoothies, treats, and even vegan options!), we headed to Arethusa Falls.
This hike was phenomenal.
The trail is enjoyable, the waterfall is impressive, and it’s an easy recommendation for anyone visiting the White Mountains.
The biggest surprise of the day came from a recommendation in our Airbnb guestbook: Lost River Gorge and Boulder Caves.
Whether it’s a true hidden gem or simply wasn’t crowded because of the weather, we had much of the area to ourselves.
Exploring caves, boardwalks, and narrow rock passages was incredibly fun, and it ended up being my husband’s favorite activity of the entire trip.
We later stopped at Sabbaday Falls before grabbing burgers from Wicked Fresh Burgers and spending the evening listening to the Ellis River outside our rental. After a long day of hiking in the rain, the juicy hamburgers and truffle fries were exactly what we needed!
Day 8: A Train Ride Into the Clouds
Another rainy day greeted us.
At this point, we simply accepted that New Hampshire was going to be wet.
After breakfast from Bagels Plus, we explored Flume Gorge.
The rain actually made the gorge feel even more dramatic, with water rushing through every crack and crevice.
Next came our ride on the Mount Washington Cog Railway.
The experience was fascinating.
The visibility, however, was nonexistent.
As we climbed above the tree line, clouds swallowed everything around us. By the summit, it felt like we’d taken a train directly into a blank white void.
Even so, the historic railway, summit museum, and sheer uniqueness of the experience made it worthwhile.
Day 9: The Day Everything Changed
We woke up to sunshine.
Glorious, perfect, cloudless sunshine.
After days of rain, the White Mountains suddenly looked completely different.
So we threw our plans out the window.
First came Glen Ellis Falls, followed by another stop at Bagels Plus. Then we made a spontaneous decision to drive the Mount Washington Auto Road.
After seeing the summit hidden in clouds the previous day, we had to know what it looked like in clear weather.
The answer?
Absolutely spectacular.
The views stretched for miles in every direction, and it genuinely felt like visiting an entirely different mountain.
After one final stop in North Conway for Local Grocer’s smoothies and chocolate, as well as a tax-free LL Bean outlet visit, we headed to Portland.
That evening we walked from Munjoy Hill down to Old Port and enjoyed a delicious dinner at Luke’s Lobster.
Day 10: Chasing Lighthouses
The day began with an unforgettable cold brew from Tandem Coffee Roasters and potato donuts from Holy Donut.
Then we headed south to Maine’s famous lighthouses.
Our first stop, Two Lights State Park, was a bit disappointing. While you can see the lighthouses from afar, both are private property and inaccessible.
Portland Head Light, however, more than made up for it.
It’s easy to understand why this lighthouse appears on so many postcards and travel brochures. Between the lighthouse itself, Fort Williams Park, and the dramatic rocky coastline, it’s one of the most beautiful places we visited.
We also explored Spring Point Ledge Lighthouse and Bug Light before returning to Portland.
The rest of the afternoon was spent shopping around Old Port, enjoying a late lunch at DiMillo’s on the Water, and wandering through local stores.
That evening, after realizing our baby had slept through Bug Light earlier, we made a second visit for photos.
The day ended with an unexpected food truck dinner from Falafel Mafia at the Eastern Promenade Food Truck Park.
The pitas were incredible!
Day 11: One Last Pastry
On our final morning, we squeezed in one last walk.
This led us to Standard Baking Co.
If you’ve ever wondered whether a bakery can be worth rearranging your schedule for, the answer is yes.
The pastries were phenomenal. We even took cookies home and immediately regretted not buying bread as well.
Naturally, we also made one final stop at Holy Donut.
At some point during this trip, we convinced ourselves that averaging 15,000 steps a day somehow offset the number of pastries, cannoli, donuts, and ice cream cones we consumed.
I’m choosing to believe that’s true.
Soon afterward, it was time to return the rental car and fly back to North Carolina.
Final Thoughts
This trip reminded us that the best travel days rarely go exactly as planned.
We skipped hikes, changed itineraries, chased better weather, and adjusted constantly around naps and feedings. Yet many of our favorite moments—the Rockland Breakwater Lighthouse, Lost River Gorge, our Cadillac Mountain pizza picnic, and the second trip up Mount Washington—weren’t even part of the original plan.
Traveling with a nine-month-old wasn’t limiting. If anything, it made us more intentional and more present.
If I were planning this trip again, I’d spend more time in Boston, possibly overnight, and less time in Portland. I’d also make room for a puffin or whale-watching cruise in Bar Harbor.
But overall? Ten days in New England gave us rugged coastlines, historic cities, mountain adventures, incredible food, and memories we’ll be talking about for years.
