Experiencing fall in Maine for the first time felt like stepping straight into a postcard. Crisp air, golden leaves, cozy sweaters, and lobster rolls on repeat. We spent the weekend exploring charming coastal towns, soaking up cliffside views, and eating as much fresh seafood as possible. The scenery was next-level, the weather was glorious, and the whole trip felt like a dream.
Here’s a peek at everything we packed into our fall weekend escape…
Travel Planning & Trip Details
Before I dive into the details, I have to give a huge shoutout to Meg of MH Custom Travel for planning the dreamiest itinerary for us. She has planned several trips for us and truly thinks of every little detail, making the entire process feel effortless. If you’re planning a trip anytime soon, she’s the best, and she’s offering my readers $75 off her travel planning services if you mention my blog!
We flew into Portland, Maine on Friday afternoon, picked up a rental car at the airport, and drove about 45 minutes south to Cliff House. It was a short weekend (we flew home Sunday afternoon), but we managed to squeeze in a lot while still keeping the pace fun and relaxing. That said, there is so much more we could have done and already have a list going for next time!
Where We Stayed: Cliff House Maine
We stayed at Cliff House, and it was the most gorgeous spot for a fall weekend escape. The resort sits right on the cliffs in Cape Neddick, and the views are absolutely insane. From the moment we arrived, I couldn’t get over how gorgeous everything was. The entire property is beautifully designed with classic New England charm. There are fireplaces tucked into corners, cozy seating nooks, an outdoor hot tub and heated infinity pool with ocean views, and thoughtful little touches throughout the resort that make it feel extra special in the fall.
Our room was beautiful, with huge windows and a balcony overlooking the water, which was our favorite spot to watch the waves crash into the cliffs while sipping on coffee in the coziest, plush hooded robes.
The food and drinks on property were five stars. Everything we ate was incredible, and we loved The Tiller restaurant so much, we ate there twice! Every bite was delicious, and the cocktails were perfect.
We also squeezed in some time at the spa, which was definitely a highlight. It was top tier with peaceful lounges to relax in and amenities like infrared saunas to enjoy before or after your treatment.
Kennebunkport, Maine
Our afternoon in Kennebunkport was one of my favorite parts of the entire trip, a true fall dream brought to life. We stopped through on our way to the resort from the airport, and within seconds of pulling into town, I was completely smitten. It felt like stepping into the most curated fall Pinterest board imaginable.
There were pumpkins lining every porch, overflowing window boxes bursting with fall color, and charming little inns that made me want to move in immediately. The whole place was so picturesque, my camera roll could hardly keep up.
We kicked things off with lobster rolls at The Clam Shack, which was our official introduction to lobster rolls, and it did not disappoint. It was the perfect way to start our seafood streak for the weekend. Afterward, we wandered the town, grabbed coffee, and soaked up every bit of the fall magic before hopping aboard The Spirit, a 125-foot schooner where we ordered cocktails and took in the views from the water.
Even though we only spent an afternoon here, Kennebunkport was one of those places that just sticks with you. If you’re planning a fall trip to Maine, do not skip it, it’s the kind of town that makes you want to come back year after year, and it was the #1 reader recommendation when I polled y’all for fall weekend destinations.
On our way out of Kennebunkport, we made a quick stop to snap a photo of The Wedding Cake House in Kennebunk, which is known as one of the most photographed houses in Maine. The storybook vibes were strong, and the house literally looked like it was magically piped in frosting.
Portland, Maine
We spent most of Saturday in Portland and booked a Seafood Lovers Walking Foodie Tour to explore the local food scene. Our tour guide, AJ, was excellent, and it was fun to hear so much interesting history about the city along the way. We got to sample some of the freshest seafood (straight off the boat!) — oysters, seafood chowder, a fish taco, a stop at The Holy Donut (which doubled as our souvenir stop for the kids), and of course, another lobster roll!
That said, I’d probably skip this tour next time. It ate up a big chunk of our day, and we were the youngest people on the tour by at least 25 years. If you’re a serious seafood person and love a guided experience, it might be worth it, but next time, I think I’d rather explore on our own and pop into a few spots at our own pace.
Perkins Cove
Our final stop before heading to the airport was Perkins Cove, a historic working fishing cove in Ogunquit. It’s a small, walkable, postcard-perfect area filled with art galleries, shops, and boats!
We were told we’d find the best lobster roll of our trip there…and that’s exactly what happened. We grabbed our final roll at Footbridge Lobster, and it ended up being the best lobster roll we’ve ever had. It was perfectly buttered, lightly dressed with just the right amount of mayo, and exploding with fresh lobster. We ate it dockside with a gorgeous harbor view and it was the most delicious send-off and the perfect way to wrap up our fall weekend in Maine!
