A Day Trip to Kennebunkport, ME

20170519_140422.jpgWe had our first heat wave of the year last week. Yes, you read that right, we had our first, three consecutive days over 90 degrees in New England…in mid-May. Sadly, neither of us got to enjoy much of it. Last week we got in a fender bender (causing slight muscle soreness and mild concussions). So on the days we weren’t recuperating, we were stuck inside our stuffy offices looking at the bright, summer sun shining from behind closed windows. We had no idea how much we needed our next trip until Friday, a day that was planned in February, finally came.

Our minds were set on our next destination months ago. It started out as a conversation about where we used to vacation in summers growing up in New England. Phil, a resident of the South Shores of Massachusetts, escaped to Cape Cod as a child. Memories of flying kites in Dennis, eating seafood in Yarmouth, sandcastle building in Falmouth, and sun bathing in Chatham flooded back to him. I on the other hand usually headed to Maine, and was generally ‘forced’ to spend weekends on the beach as a tween for two weeks out of the summer – York, Maine specifically. Before the microbrews and the herds of busses rolled into Nubble Light, Long Sands and Short Sands beaches were different. Fifteen years ago they were quieter, almost dull and boring (at least in the mind of a 10 year old, longing to do cannonballs off her friends diving board at home). Today, at at almost 28, it seemed heavenly. We also considered the fact that it was the weekend before Memorial Day – the unofficial kick-off to Summer, long weekends and even longer lines of traffic weaving out of Boston on Friday afternoons. We wanted to travel to a destination that we wouldn’t dare go during peak season. Decision made: a day trip – a way to save some money in hotel fees, but also explore one of the places we never did as kids, a place that some famous Bushes vacation: Kennebunkport, ME.

Kennebunkport is a mere 1.75 hours northeast of Boston by car, but we wanted to make the most out of our day off. After packing some quick essentials, including that ever-important bathing suit and beach chair as well as sneakers, we were off to grab breakfast in Portsmouth, NH as it was a little too early for us to eat when we left. We were on Route 95 in a jiffy; we quietly laughed at all of the commuters heading into the city as we were headed out. It only felt right that we blasted some 60s rock classics like ‘Born to be Wild’ and cruised northward.

Technically, Friday was not part of our heatwave. But it still was a warm 75 degrees at 7:30 in the morning with a lovely dew point of 65, making it feel like a late July day rather than the middle of May. After scarfing down some delicious food at Colby’s downtown and making the most of our meter payment with a little saunter around downtown Portsmouth, we were off again, but this time we took the scenic route: Route 1.

Once in Kennebunkport, we felt like little kids again! We didn’t have a plan or even a remote idea of what to do that day and it felt great, and that’s coming from a neurotic planner. We popped in and out of shops, had seafood that would satisfy even the most picky foodie, and even got some well-deserved laughs biking through downtown and back roads. What an escapade!

Keep reading for our itinerary of the must sees on a day trip to Kennebunkport, ME!


A day trip to Kennebunkport, Maine

Key Pointers

  • Be prepared. Though we didn’t end up going to the beach to lounge around, we did rent bikes, so my converse sneakers were a welcome accessory. There are also other options for activities, including, paddle boarding and kayaking. Bring sneakers, a bathing suit/towel, and water shoes, just so you don’t miss out on the fun due to your outfit choice.
  • Want to make the drive a little more fun? Break up your trip with a stop in Portsmouth. There are amazing local establishments to window shop and so many little cafes that make a great spot for breakfast, or an afternoon snack.
  • Take your time! If you’re not in a rush, take Route 1. This scenic route offers the most amazing scenery (picture majestic mansions on your left and cliffs leading to the ocean on your right) for miles and miles.
  • Bring a car! There are dozens and dozens of antique shops lining Route 1. You never know when you may see your next show-stopping piece for your home along the way!


Where to eat, drink, and be merry:

  • Federal Jack’s: They claim to be birthplace of the famous Shipyard beer. Head inside to order one of their locally sourced brews. Then head outside to enjoy the cool drink on their deck overlooking the Kennebunk River.
  • The Clam Shack: Some of the freshest seafood around. Try the lobster roll with a pint of fried clam strips on the side. They do not disappoint!
  • Rococo Artisan Ice Cream: Looking for a sweet treat to cool you off in the summer heat? Try one of the amazingly unique flavors at Rococo. And when I say unique, I mean Earl-Gray-Sour-Cherry-Jam-with-Pistachios kind of unique.

This slideshow requires JavaScript.

What to do:

  • Stroll through Dock Square: If finding trinkets is a must when traveling, this area is the perfect spot. Be sure to shop small and stop in Dock Square Emporium – you won’t be sorry.
  • Walkers Point: Yes, this is where the infamous complex is located, owned by Former President Bush and company. It is a sight to see, even if you’re not really into the whole tourist thing; the drive to the Point is breathtakingly picturesque.
  • Coastal Maine Kayak and Bike: For a measly $10/hour, rent colorful bikes to weave around the city on two wheels! This was the highlight of our trip, riding along the water, up the hilly back roads, and zipping through town. It satisfied our need for childish fun while also allowing us to gawk at that amazing homes along the water.

This slideshow requires JavaScript.

3 thoughts on “A Day Trip to Kennebunkport, ME

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s