Road-Trip Second Stop: Kennebunkport, Maine

On to the next day!

Day 2 of our roadtrip took us up to the quiet area of Kennebunk and Kennebunkport, Maine!

This day wound up being joyously random and we went where we felt we wanted to go without a plan in the world! We spent the morning scoping out Boston and getting a whirlwind tour of the city. Thanks to that gnarly jetlag, we were up and at ‘em really early which gave us a great chunk of the day to mosey around Boston.

Then we hopped in the car and headed North!

Originally, we had planned to go deeper into Maine, but ultimately decided on staying in the Southern tip of Maine and did some googling (aka searched my Hilton Team Member discount website for the best deal!). True story, I had seen a couple Bachelor alums vacationing in Kennebunkport on IG and was about to suggest it as an option to my roadtrip buddy Anna, and she literally messaged me at the same time suggesting it, so that was that!

Kennebunk and Kennebunkport are actually two different towns about 15 minutes apart. If you guessed that Kennebunkport is on the water and Kennebunk is more inland, you would be correct! For the sake of the rest of this post not being dull, Imma use both interchangeably and will designate when it fits, okurrrrr?

Both are about an hour and half to two hours north of Boston, so they make for a great weekend getaway from the city! We stopped in Salem for lunch along the way and it wound up being a great halfway point and little mosey around another cute Massachusetts town! We didn’t get a chance to go to the Salem Witch Museum but if you’re interested there are a few different options there so maybe pencil in a few extra hours for your stop!

We made a few pit stops so I could show off Target and so we could get road trip essentials before we got seriously into the drive!

I’m a sucker for the New England coast and Kennebunkport has everything that makes me a sucker for it.

Photo Courtesy of Hampton Inn + Suites Kennebunk Kennebunkport

We stayed in Kennebunk, at the Hampton Inn Kennebunk, and I would definitely recommend for anyone looking to go out or meet people to stay in Kennebunkport proper. It’s about a $15 USD Uber/Lyft to get into the town so if you’re going to head there every night, it makes sense just to stay there at the end of the day!

Kennebunkport is a quiet little village that comes alive during the warm summer months. We wound up eating at essentially the only place open past 9pm, Allison’s, which is so fitting for a New England coastal town. The food was great, my seafood risotto hit the spot and opened my seafood palate right up!

We asked the server at Allison’s where the locals go, and were told The Pilot House was the place to go. She was not wrong.

Side note: We adopted this method for pretty much our entire trip and were never steered wrong! If you’re looking for a local spot and to actually experience a town, ask the people that work in hospitality. They always know the ins and outs of the good spots to go in town and where to stay away from!

The Pilot House is right by the bridge in town and is a great mix of locals and tourists and summer washashores. We played many rounds of tourist or local and were almost always wrong! Everyone was friendly, everyone was sunburnt, and everyone was drunk.

Enjoy some bevys to wash the day away at this open air spot.

We spent the next morning wandering around town, and especially made sure to take in Dock Square where we did some shopping and enjoying that salty summertime air! It’s a really adorable little downtown area with colorful shingled houses and a quaint little bridge!

If you’re gluten free I found a hidden gem at Moon Rose Cafe: GLUTEN FREE BAGELS! Stock up, they are delicious!

And unfortunately, we were on a whirlwind tour, so we were off to our next destination: PROVIDENCE, RI.

If we had time to stay, or when I get an opportunity to get back (which I certainly will next year on the way to WITS in May!) these are the things that are on my list: 

  • Biddeford Pool: Constantly voted Maine’s most beautiful beach! I’d probably go straight there without even checking in! It’s a beautiful beach that has little to no development because of old zoning laws. So enjoy the tranquility.
  • St. Ann’s Church: A gorgeous stone chapel, a rare find on this side of the Atlantic!
  • Ferry Beach State Park: Miles and miles of white sand beaches and a rare gaggle of tupelo trees (black gum) grace this 100-acre state park.
  • I’d drive Ocean Avenue and watch the waves hit the rocks! This road runs along the coast of Maine and offers tons of breathtaking views!

Hope you enjoyed this quick Maine tour! On to Providence for Day 3!

Megan Stetzel

Megan is a girl that shouldn’t travel. She’s gluten free, allergic to everything else, falls off motorcycles, poops her pants, gets bit by stray dogs and yet she’s still been traveling the world. She's the co-founder and editor of Why Wait. Read More About Megan here.

View Comments

1 thought on “Road-Trip Second Stop: Kennebunkport, Maine”

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.