Memories In Maine: Our Family’s Fall Adventure
Visiting Maine in the fall has always been a bucket list trip for our family. At the end of September, when the kids had a short school break, we finally made it happen. Since time was limited, our stay was only 6 days, but we fit a LOT in that I’m excited to share so you can plan a similar getaway. In this blog, I’ll break down our itinerary along with lessons learned, so let’s jump in!
Welcome to portland!
We flew in and out of Portland, which was a convenient location that enabled us to explore the northern coast. Temperatures swung from chilly nights to warm afternoons, so we packed for multiple seasons, but still managed to avoid checking bags, thanks to this packing must-have I never travel without. I consolidated to one barn jacket and absolutely lived in this the entire time!
We rented a large SUV and ate lunch at Luke’s on the water, a popular pier-side spot, that was worth the wait. Our lobster-loving son enjoyed it so much that we went back on our final day.
To maximize our short trip, we tackled the longest drive on Day 1, heading three hours north so we could work our way back down the coast toward Portland.
After a long trek, we arrived at our first stop. . .
Glamping at Under Canvas Acadia
Our trip started on a high note: two nights glamping under the stars at Under Canvas Acadia. This magical retreat sits on 100 acres of waterfront, surrounded by nature. One morning, a family of deer wandered right past our tent and later that evening, we spotted a cluster of porcupines scurrying nearby.
If your family loves the idea of camping, but prefers basic comforts like us, this spot strikes the perfect balance and here’s why . . .
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Happy Campers
They have multiple tent options to choose from, but we chose the Suite, which fit our family of four perfectly. David and I had a cozy king bed, while the kids shared a queen-size sofa bed. The best part? Running water inside the tent, complete with a toilet, sink, and even a hot shower.
There’s no WiFi or electricity in the tents (though you do have cell service - we have AT&T), and the main restrooms offer outlets if you need them. What turned out to be most critical, however, was the wood-burning stove. On our first night, unexpected freezing temps rolled in. Cue lots of laughs (and some complaints) as David faithfully poked the fire every couple hours to keep it going.
If you’re visiting during colder months, here are my top tips:
Keep extra logs and fire starters [inside] of your tent
Ask for zero-degree sleeping bags for the kids (we didn’t learn about these until night two!)
Pack long underwear, hand warmers and winter layers if the forecast looks chilly
By night two, we were pros and, honestly, those first-night mishaps turned into some of our favorite memories.
On-Site Amenities: Food, Games & Family Fun
The main lobby tent at Under Canvas Acadia is the heart of the property. This is where you’ll find seasonal meals, drinks, live entertainment, scheduled activities, and an incredible staff who can help with everything from fresh linens to local hiking trail recommendations.
During our stay, we loved the community atmosphere. On our first night, a talented local singer performed, filling the lobby with music. The second night, we played family-friendly games (provided on site) and even reconnected with friends who happened to be glamping in Maine at the same time.
The food was another highlight - fresh, seasonal, and, surprisingly, delicious. We happily ate both breakfast and dinner on site each night, which made the experience even easier with kids in tow.
I brought my trusty portable chargers for each of us, but, turns out, each tent comes with one for small devices, and you can even recharge it at the lobby whenever needed, which is a thoughtful touch.
Acadia National Park
Just 40 minutes from Under Canvas, Acadia National Park is a must-see. With miles of hiking trails, you’ll find colorful forests, rugged coastlines, and views that feel like a postcard come to life.
What to Know Before You Go:
Fees & Passes: Register here online in advance to pay park fees and secure required passes.
Cadillac Summit Road: Reservations are mandatory during peak seasons. We couldn’t squeeze it in this trip, but it’s a top sunrise spot we’ll return for next time.
Footwear: Trails range from flat paths to rocky ledges. Sturdy hiking boots are a must. I wore my go-to boots (the same pair I used in Alaska) and highly recommend them.
Great Head Trail (2 miles, easy to moderate):
We chose this short, but stunning loop and loved every step. The mix of lush forest and dramatic coastline kept it interesting and Sand Beach was the highlight. If you’re short on time like we were, this trail is ideal. A mixture of flat paths and rocky ledges, appropriate footwear is suggested.
Gone Fishing
On the way from Acadia, we stopped in Bar Harbor for lunch at Stewman’s, a great spot to fuel up before a day on the water. From there, we headed to Beech Hill Pond, a crystal-clear lake surrounded by charming waterside homes.
Our son, who usually reels in largemouth bass back in Georgia, had his heart set on catching smallmouth bass and other native species. To make it special, we booked a private guide with Eagle Mountain Guide Service. Matt, a retired Veteran, was incredible. He shared local fishing knowledge, taught new techniques, and even introduced David and Landon to trolling equipment for salmon.
Although we were late in the season and didn’t catch much, the four-hour excursion was still a highlight. Reagan, who had never fished before, loved the experience, and I enjoyed soaking in the peaceful views because . . . sometimes, it’s less about the catch and more about the memories.
Tip: Buy a Maine fishing license in advance here (required for ages 16+)
Spruce Point Inn at Boothbay Harbor
After two adventurous days up north, we headed south to Boothbay Harbor and checked into Spruce Point Inn. After glamping under the stars, the whole family was ready for central heating and air and this charming coastal resort did not disappoint.
Perched on the rocky shoreline, the Inn offers sweeping harbor views and a peaceful, New England feel. The kids especially loved kayaking straight from the pier, while I soaked in the views with my morning coffee. Spruce Point Inn felt like the perfect balance of comfort and seaside adventure, a welcome reset before continuing our Maine road trip.
Boothbay Harbor - Dining & Exploring
We kicked off our Boothbay Harbor experience with lunch at Kaler’s, a waterfront favorite so good we went back twice. (Pro tip: try the lobster rolls and chowder - you won’t regret it!)
Downtown Boothbay is straight out of a Hallmark movie, with its charming streets, local shops, and picture-perfect harbor views. We spent the afternoons strolling, shopping, and soaking up the cozy small-town vibes.
In the evenings, we enjoyed drinks at the Spruce Point Inn bar before venturing out to dinner. Night one took us to Harborside 1901 Bar & Grill, and on night two, we dined at the Thistle Inn, where we were lucky enough to meet up with more friends in town.
Tip: Reservations are highly encouraged for both Harborside 1901 and Thistle Inn.
Come Sail Away With Me
No trip to Maine feels complete without time on the water, and our day sail with Boothbay Sailing aboard the Schooner Eastwind was unforgettable. For two hours, we glided along the coastline, passing lighthouses, remote islands, and wildlife at every turn. We spotted seals, porpoises playing in the waves, and gulls soaring above - it felt like the perfect postcard come to life.
One of the highlights was that the crew encouraged participation. Guests could help raise the sails so, of course, David jumped at the chance. It was such a fun, interactive touch that made the experience even more memorable.
Onboard, they serve a variety of drinks (both alcoholic and non-alcoholic), and there’s a restroom available, but no snacks, so be sure to eat beforehand.
Tip: The Schooner Eastwind is a family-friendly way to experience Boothbay Harbor from the water. Book in advance during peak season to secure your spot!
Portland - Lucky Catch Lobster Tour 🦞
For our final stop, we landed back in Portland where we booked a private lobster excursion with Lucky Catch, and it turned out to be the highlight of the entire trip. For two hours, we cruised around the harbor, checking traps, learning the ins and outs of Maine’s lobster industry and the rich harbor history.
The crew explained the rules of lobster fishing and even taught us how to tell males from females. The most fascinating moment? Pulling up a trap with a pregnant lobster carrying hundreds of eggs. Of course, she was released back into the ocean to help sustain Maine’s lobster population, which was a hands-on lesson in conservation.
Pro Tip: Hire a Photographer
To make this experience extra special, I booked local photographer Adrianna Lynn to capture candid family photos during the tour. It was the best decision so I could relax, enjoy the moment, and end up with photos we’ll cherish forever (without a single forced smile).
Inn at Diamond Cove
Full disclosure: I didn’t realize the Inn at Diamond Cove was on a private island that required a ferry . . . Oops! It came highly recommended by friends I trust, so I booked it without digging into the details. After the sailing excursion, we missed the public ferry and had to hire a private water taxi both ways to make our flight home the next day, which was not cheap, but definitely a unique experience.
Once we arrived, though, the property was stunning. Diamond Cove is a small private community with beautiful residences, and the inn itself is located inside renovated Fort McKinley, which once defended Portland Harbor during the Spanish-American War. The history and charm were undeniable, and we enjoyed our short stay.
That said, it’s a very quiet property. While it’s gorgeous and peaceful, it may not be ideal for families with young kids for an extended visit. If you’re looking for a serene, historic getaway (and don’t mind the ferry logistics), it’s definitely worth a stay.
Parting is such sweet sorrow . . .
Visiting Maine in the fall truly lived up to our bucket-list expectations. Even though the state was experiencing a drought that muted some of the iconic leaf change, we still found brilliant bursts of red, fiery orange, and golden yellow along the coastline. The crisp air, charming small towns, and scenic drives created the perfect backdrop for our family adventure.
The cooler autumn temperatures made every activity more enjoyable. Pair that with cozy accommodations, whether it’s glamping under the stars, a seaside inn, or a historic hideaway, and you’ve got the makings of a trip that balances outdoor adventure with plenty of comfort.
For us, Maine in the fall was peaceful, inspiring, and unforgettable. We left with full hearts, cherished memories, and a strong desire to return one day—because there’s still so much more to explore.
