Travel Diary | Autumn in Maine

When Andrew decided to attend college in Boston, one of the first things I started doing was plotting 4 years of autumn visits to New England. My favorite season, in my favorite part of the country - this was almost a fair trade off for him not attending a school closer to home. This year we choose Maine, next year I’m thinking Vermont. Thankfully, Charlie’s fall break coincided with family weekend at Emerson but instead of staying on campus we decided to spend a long weekend out of the city and head north. I knew Andrew would be ready for a break from dorm room living since he won’t be home till Thanksgiving.

We arrived on Wednesday in time to grab dinner with Andrew in Boston and as soon as he wrapped up classes on Thursday we were on our way out of town. First stop was Portsmouth, NH which took me by surprise - what a thriving, charming and beautiful city! We walked around town a bit before enjoying an exceptionally delicious dinner outside at Cure. The chocolate lava cake with peanut butter sauce was next level. Highly recommend. It felt so good to be a complete family of 4 again. I couldn’t stop smiling.

We ended up arriving in Cape Porpoise, Maine after dark, to the most charming “Captain’s Cottage” rental. Cape Porpoise is the fishing harbor village of Kennebunkport. It’s this unassuming, small community with a handful of great restaurants, a few shops, a market, a library and a classic New England, white steepled church. We were greeted by the crunch of our car on the shell driveway, the smell of pine heavy in the air, bud vases with wildflowers from the garden, bells marking the hour from the church across the street and extra cozy beds. Jimmy and Andrew took a walk down to the harbor while I unpacked and settled us in. It wasn’t long till we were all fast asleep.

Our mornings quickly fell into a routine - Jimmy and I up before the boys, we’d walk across the street to the bakery to grab coffee and breakfast and then down to the pier at the end of the street to enjoy the pretty view of Goose Rocks Lighthouse in the distance and the bobbing of fishing boats closer to shore. Once the rest of the gang was up and ready, we would head off to explore. We visited Kennebunkport and Ogunquit, we went apple picking and on a lighthouse bike tour in Portland, we ate the best cider donuts I’ve ever tasted, saw the cutest pumpkin stands, picked up little treasures and souvenirs along the way, and ate daily lobster rolls. We also celebrated Charlie’s 13th birthday! The boys stayed up late each night watching scary Halloween movies and we officially added Maine to our list of places where we could happily retire one day. It’s also possible that Maine has the friendliest people too.

As much as I loved the years of having little kids and the excitement of Halloween costumes and pumpkin patch visits, I can honestly say this past weekend was my favorite fall weekend ever with my sons. And we still did all the traditional fall things including farm visits, wagon rides and a corn maze too. Here are a few highlights and places I recommend.

Cape Porpoise Kitchen (Bakery and gourmet food shop with lots of prepared meals. The food is exceptional. Arrive early if you want baked goods in the morning. The pumpkin muffins and cinnamon rolls are insane, best I’ve had that I haven’t made myself. Great place to grab lunch for beach picnic or easy dinner. (Reminded me of what I imagined the Barefoot Contessa shop to be like in the Hamptons when she still had it)

The Ramp Bar and Grill - Iconic casual Maine dining and bar right on the water - we loved it. Full of sports and political memorabilia. (Note, it’s small and cozy inside, so if you aren’t comfortable sitting close to others with the pandemic, you may want to skip.)


McDougal’s Orchard - Apple picking and the BEST cider donuts. We ordered a bucket of donuts, yes, a bucket, and ate every last one. I heard their cider is incredible too. The farm is large and the people that work there are exceptionally friendly. We also did a wagon ride and a short corn maze. It’s all very authentic, working farm, no bells and whistles, carnival rides or photo backdrops - just the way I like it.


Snug Harbor Farm - This place has been on my bucket list for a while and it didn’t disappoint. If I ever had a shop I’d want it to feel just like this. Such an inspiring place and a must visit if you are in the area. Be sure to walk the whole property.


Lighthouse Bike Tour - We had a gorgeous late afternoon guided bike ride.


Marginal Way - Cliff walk in Ogunquit with stunning views.

Seacraft Vintage - Paul Havel and Jackie Greaney’s shop. A little gem of an antique shop in Kennebunkport. It’s outside of the main shopping area. We walked and it is very doable on foot. Maybe a 10-12 min walk from the center of town. There is a coffee shop along the way too if you need a little pick me up.

Timber Steakhouse - We celebrated Charlie’s birthday with dinner here and it was delish! The calamari appetizer was my favorite part of the meal.

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