If I could just bottle up Kennebunkport, Maine and keep it in my pocket… it’s like I’d always have a little piece of heaven with me. Really, that’s how I felt after a quick 48-hour weekend trip to the seaside town with Jeff.
I’d always heard that Maine, specifically the town of Kennebunkport, was basically the most a-mazing little village… but until I had experienced it myself, I hadn’t really truly believed it.
After finishing up work on Friday, we hopped in the car and drove an hour and a half north of Boston, slowly cruising through the town, ooh-ing and aah-ing at absolutely everything, before finally pulling into the Captain Fairfield Inn, one of the Lark Hotels boutique properties.
Situated just a block away from Dock Square (essentially the village on the water with shops, restaurants, etc), not only was the Captain Fairfield Inn in the perfect location – but it had to be the cutest bed & breakfast I’ve ever experienced. Built in the 1800s, it is the original home of Captain James Fairfield, a Maine native who eventually became a sea captain.
Captain Fairfield didn’t have the best ending. Eventually, he passed away from pneumonia, and his wife ended up selling the home. Years later, it is said that a portrait of Captain Fairfield was found on a boat at sea — and now, a replica sits near the front entrance of the inn.
Once we arrived, we were greeted by Captain Fairfield (his portrait, not him!), before heading into our absolutely beautiful room. From the hardwood floors, to the stunning wallpaper, to the bathroom of my dreams (I took photos for future inspo).. oh, and a door to a private deck… if I had the chose to stay there forever, I certainly would.
Eventually, I realized we should probably go explore the town, so the next morning, after waking up and stuffing our faces with a delicious breakfast from our generous inn keeper, we got back in the car to begin our adventure.
Sadly, it was drizzling, or else we’d try to walk every where, but we made the best of a rainy day by driving to the beach and then to Cape Porpoise.
Luckily, as we approached small coastal village of Cape Porpoise, the clouds and fog drifted away and we were greeted with an amazing view of the lighthouse in the distance.
After snapping a few photos, we turned around and came across one of the restaurants that had been suggested to us — The Ramp. Tucked underneath Pier 77, we walked into an explosion of sports and political memorobilia. It literally covered every wall, from floor to ceiling.
Once settled in with a beer, we chowed down on crab cakes and lobster rolls, all while watching the lobstermen cruise by on their boats. Very full & satisfied, and with the rain finally over, we figured it was the perfect opportunity to drive by Walker’s Point to get a glimpse of the Bush compound (the family’s summer home) before heading back to the Captain Fairfield Inn.
With the rain starting again, Jeff and I got in a little work before researching a few spots to watch the Kentucky Derby. We ended up choosing David’s KPT after receiving a few recommendations on Instagram — and we’re so glad we did. Right on the waterfront, we snagged two seats at the bar, ordered some wine & cheese, and sat back to watch the final races.
Once the races were finished – we started to think about dinner plans. I know, it seriously sounds like all we do is eat when traveling, ha! The couple sitting next to us at David’s KPT would not stop talking about a restaurant called Earth… and 15 minutes later, we were walking into one of the coolest restaurants I’ve ever been to. I can’t even begin to explain the decor — it was that breathtaking (think very rustic chic – yet feeling like you’re camping in the woods). After trying to take it all in, we ordered dinner, and enjoyed one of the best meals I’ve had in awhile. The farm to fork menu was so delish — we already started planning our next visit back.
The next day, I was on a mission to find a cute coffee shop – as I have an obsesssion with iced coffee. A quick 5-minute walk from the Captain Fairfield Inn, we stumbled across Dock Square Coffee House. After ordering our coffees, we were lucky enough to find a table by the windows, over looking the water once again.
Of course, weekends always seem to fly by, and once finished up with coffee, it was time to pack up and start driving back home to Scituate, MA. But, not without a stop at the Cape Neddick Lobster Pound for their humongous lobster rolls and a pit stop at Nubble Lighthouse before getting on the road.
Overall, I’m already dreaming of my next trip to Kennebunkport, hopefully this time with a bit more sunshine and beachtime. Until then, I’ll reminisce about the quaint seaside town, wishing I could teleport on days that I’m craving a relaxing weekend in Maine.
Where We Stayed
Captain Fairfield Inn
8 Pleasant Street
Where We Ate
Dock Square Coffee House
Earth at Hidden Pond
Cape Neddick Lobster Pound
What We Saw
Cape Neddick / Nubble Lighthouse