A weekend in Portland, Maine with a toddler

by Jessica Pawl

I’d love to romanticize the reason we packed our bags and flew to Maine. But the truth is that we were too scared to fly further than two hours the first time we had our kid in tow. So, we paired proximity with butter-drenched lobster rolls and ocean views, and had ourselves a vacation plan.

Tackling Maine in one week felt tricky, given that there’s so much to explore. But we strategized and squeezed in three stops:

Portland: For it’s seafood saturation and authentic Old Port walkability. (Plus, it’s the city we’d fly in and out of.)
Acadia National Park: Because how could we skip it? Gorgeous hikes, a sweet small town and a very cool camp-style lodging experience.
Kennebunkport: Stunning stretches of beaches, undeniable coastal charm, and a relaxed setting to end our trip in.

In hindsight, that was an ambitious plan with a tot (not to mention the unpredictable spring weather). If I could go back in time, I’d whittle our itinerary to two stops or extend the trip two more days to lessen the get-up-and-go. But for a solo traveler or a couple who doesn’t mind moving, hitting all three locations is completely doable.

A Taste of Maine food truck… an $80 meal that was shockingly entirely worth the cost

IN PORTLAND:

We began in Portland, where we flew in, rented a car and stayed two nights in a compact-but-cozy West End Airbnb, which was walkable to Old Port and the promenade. (It slept two, plus our babe in a travel crib.)

While we haven’t stayed in these vacation rentals, they meet our standards for fun family travel and are worth a look: A cheerful two-bedroom with a yard on Munjoy Hill; a cozy three-bedroom with a back patio; a four-bedroom bohemian condo with a lovely garden.

We strolled the Old Port, popped into small shops, swung by the seafood market (where Mack touched his first lobster) and found seaside playgrounds perfect for lazing away an early evening along the promenade.
We indulged in a memorable seafood dinner at Scales Portland, but there are PLENTY of amazing dining options; it’s a foodie town! Eventide is a great option for ordering ahead so that you can grab and go with the kiddo. (Don’t sleep on Holy Donut Maine, known for their potato-based pastries.)
Visited the Cape Elizabeth lighthouse at Portland Head Light – one of the most photographed lighthouses in the country – and ate our favorite lobster rolls of the trip from the A Bite of Maine food truck. (Try the wasabi roll!)
Listened to live music, enjoyed cocktails and food trucks (available on Thursdays and Fridays at “Summer Sunsets”) at family-friendly Thompson’s Point, near the airport and a perfect post-travel stop and space to run around.
An evening visit to the Eastern Promenade Children’s Park was the perfect way to let our toddler run about while taking advantage of lovely views and the convenience of parked food trucks.

IN ACADIA:

From Portland, we headed north, having set our sights on Acadia National Park. Our arrival coincided with the seasonal opening of Under Canvas Acadia’s luxury tents, which I’m certain we would have loved if it had been just a bit warmer and drier. (It was misty and magical all the same, but I wouldn’t recommend shoulder season stays while traveling with a one year old, quite frankly.)

Stopped into adorable harbor towns like Camden en route and – of course – couldn’t miss stocking up at the L. L. Bean flagship shops in Freeport. Campus might be a better descriptor, it turns out, and just FYI there are loads of additional stores (think outdoorsy outlets) in the small town.
Once we’d checked into our tent, we spent our mornings and evenings leisurely, heading to the main tent for breakfasts and dinners and soaking up the sunsets and bonfires at camp.
Drove through the quaint town of Bar Harbor, which was solidly packed with pedestrians and vehicles on a holiday weekend. Then, when we finally snagged a parking space in Acadia, we hiked the Great Head Trail in a misty rain, and threw down a blanket to lounge at Sand Beach. (Stopped by Jordan Pond House, but didn’t wait long enough to try the popovers, sigh) and walked the scenic pond pathway while Mack napped in his stroller; it was worthwhile and gorgeous, even in the drizzle.
Heading back south, stopped at Owls Head Light Station and LOVED the quiet, rocky beach.

A stop and splurge at the LL Bean flagship shops

Our Great Head Trail hike, in the rain (plus our new LL Bean gear… ha)

Home for two nights – Under Canvas Acadia

The main tent “lobby” at Under Canvas Acadia

IN KENNEBUNKPORT:

Our last stop, we stayed two nights at the adorable Marsh Cottage Airbnb just outside of Kennbunkport’s picturesque downtown. The idea was to squeeze in one last Maine perspective. We’d seen urban and remote, and now we wanted a taste of the state’s coastal charm.

From our Airbnb, we biked to and picnicked (twice) at the gorgeous Goose Rocks Beach, which was a ginormous swath of sand that we nearly had to ourselves.
Spent a whole day soaking up the sun in nearby Ogunquit and leisurely walked the iconic Marginal Way path to the local’s favorite lobster shack, Footbridge Lobster, which I can wholeheartedly recommend.
Strolled and shopped Kennebunkport and threw back oysters and drinks on The Spirit – a restaurant and bar housed on an ornate ship – docked in the harbor.

Finally, warm weather! Testing out the tides in Ogunquit

Coastal charm and decor in this tiny cottage

KEY TAKEAWAYS:

Traveling with Tots

Maine is beautiful. The food is fantastic. Traveling with a one-year-old is hard. 😂 But totally worth it.

Prepare yourself. You’ll be moving at a different (read: slower) pace. You’ll need an endless supply of snacks and gear for all types of weather. Strollers that recline, like our BOB jogging stroller, came in handy on the rough terrain and also when nap time rolled around and we were still out and about.

But mostly, simply take the time to appreciate sharing the world with your kid. Will they remember it? Likely not. But you’ll have a whole camera roll of photos to show them and a slew of stories to share. And – most important in my book – you’ll be instilling a sense of adventure in your child from a young age.

Camp-Style Accommodations

Booking a tent, in Maine, in May, might’ve been a bit risky. It was cold. It rained. And for as fancy as these beautiful tents are, there’s still no electricity and the shower has a pull-chain to operate.

(Note: I’ve learned now to fully prepare your travel partner for certain amenities – or lack thereof … like, heat – before arrival at your lodging.)

That said, we wouldn’t have traded our soggy stay at Under Canvas Acadia. It was such a cool experience, and having only opened at the beginning of the prior month, it was truly a chance to be among the first to explore. We (i.e. Trevor) tended a nightly fire to keep us warm and snuggled in a super cozy king bed, we headed to the main tent for breakfast and dinner each day, and we adventured out to Acadia to tackle some trails in between.

If you’re into the idea of roughing it, but want to take the easy way out, consider checking ‘em out! There are several in the U.S., most all right by national parks.

Hopping from place to place

We moved around a lot for a one-week trip with a little one. And yet, I struggle with the idea of cutting out any one of our stops. If given the choice, I’d extend travel by two days and give ourselves an extra day in Acadia (if to account for potentially crummy weather alone!) and an extra day in Kennebunkport to relax and still the adorable towns.

That said, I really enjoyed the road trip component of this trip! Driving up and down the coast, swinging into little seafood restaurants and food trucks, stopping to gawk at gorgeous ocean views and climb lighthouse steps… it was perhaps the most memorable portion of our getaway.