New England Road Trip: Kennebunkport, Rockport, & Cape Cod

K E N N E B U N K P O R T, Maine (30 min. from Portland)


This little town was on our route and sadly the weather was not good to us during the 30 minutes we were there. We decided to keep driving after James had his time out on the beach with his GoPro in the freezing rain. Kennebunkport, you were cute. You were quaint. I hope we get a chance to meet again because we didn't spend much time with you.

Side Note: We have watched some of the footage from James' GoPro and it is amazing. I hope you have the opportunity to see it. Actually, you probably will. He is making a video. Stay tuned.


R O C K P O R T, Massachussetts (1 hr. & 30 min. from Kennebunkport)


You were one of my absolute favorite places. You were also freezing with rain but we ate lobster lunch in your town and it was delicious. The lobster basically melts in your mouth up north. SO. GOOD. I am not a food connoisseur, but James and I are a bit of critics when we eat out, it's our thing. Sooo it probably sounds gross - but that's the closest way to describe the goodness of their lobster.  Anways - 


Rockport, AKA Sitka, Alaska (where the Proposal was filmed) was the most charming town I have ever been to. Did you know towns like this actually exist?? Obsessed.


We ate inside at Roy Moore Lobster Co. where the wall was floor to ceiling windows looking out over water, and to be honest, I think the weather added a touch of dreamy to the town. It wasn't the weather we hoped for, but looking back it made it that much more magical.


C A P E  C O D (about 2 hrs. from Rockport, MA)

The road trip was James' favorite part. Literally. The driving in the car. LOL. We have always been a lover of road trips, so this doesn't surprise me. We played Ben Rector's 4 newly released songs at the time until we knew all the words, and then we listened to James' work out playlist. Needless to say, it was a good time. We had a lot of iced coffee, a lot of laughing, and a little bit of quiet. It was the perfect balance!!

Got to our AirBnB in Hyannis, MA which is the port town in Cape Cod and walked to find the nearest grub. Can I say Cape Cod was weird to us? Okay. Cape Cod was weird. At least it was that night. Not a lot of traffic coming through the side of town we were in, and a lot of boarded up buildings. I think the weather had a lot to do with some of it, but it was strange to say the least! We found a charming little place to eat at Portside Tavern and called it a day.


We spent the following day touring the towns around Cape Cod. This was one of my FAVORITE days! All the towns were so unique and had their own personality. Here are some of the things we did in. one. day.

  • Hyannis (the port town): JFK Legacy Trail walk & see those cape cod homes you are looking for, JFK Memorial- guys, this was a beautiful memorial!!
  • Barnstable (charming & probably my fav!): Iced coffees at Nirvana Coffee Company, ate lunch on the patio at The Barnstable Restaurant & Tavern (they had a great lunch menu!), and take the time to really walk around the town and soak in the area - it's so so dreamy!!!!
  • Dennis (didn't spend much time here): Ate dinner at Cleat & Anchor and participated in a Music Bingo night. I need to add, that I won a round. That's all. Also in Dennis is The Sesuit Harbor Cafe that we didn't get a chance to eat at, but we did drive by while it was raining (outdoor only) and I have to mention it because we are sad to have not been able to go there!
  • Yarmouth: drove through suburb type area
  • Provincetown (tip of the cape): you get your own post on your own day ;).

Looong post, if you read it all. bless you!!!

XO, Meredith