Last year for my 30th birthday, I wanted to go somewhere phones weren’t needed. I was looking for a cute small town where you could wander around and find things to do, but didn’t need your cell phone to help you figure out how to get back to the hotel. This is very similar to how Highlands, NC is, which is our favorite local getaway, but since our wedding was only a few months away, I wanted to choose somewhere a little further away.

Kennebunkport checked off all of the items on my list, and was easy to say yes to! Small costal town with cute boutiques, luxury hotels, and great food…LOBSTER! We decided to fly into Boston on a Thursday, as the flights were more convenient than Portland, and rented a car for our long weekend. The drive is a little over an hour from Boston, but it was very easy. Quick note: Kennebunk and Kennebunkport are RIGHT next to each other, just on the other side of a small river, attached by a bridge. You won’t know the difference!

We stayed at The Grand Hotel Maine, one block from the river. There are many small boutiques to choose from, but we really enjoyed the quality for the great prices here. The staff were extremely friendly, and there was a lovely little breakfast set up every morning in the lobby.

Friday was my birthday, so we slept in and grabbed some breakfast in the lobby before decided to start exploring. We wanted to see the Bush Compound, so that was our first “stop.” Notice the quotes as you are NOT allowed to stop, there are many signs letting you know. We kept driving to the next little town over, Cape Porpoise, and noticed a few restaurant looking places along the water. It took a little driving, but we finally found The Ramp, which was exactly what we were looking for! It was a dive bar that served the best lobster rolls. It is below another restaurant so its a little dark, but has windows that open up to the water for a view of the tides coming in and out. The walls are adorned with memorabilia and signatures. You’ll want to look closely, as you will see MANY that you recognize. It was well worth the 15 or so minute scenic drive for lunch!

For my birthday, the husband had planned a great spa treatment at the White Barn Inn, and Aubergine Hotel in Kennebunkport, so we headed that way with our fancy clothes as we had dinner afterwards. The spa was fantastic and so relaxing. After we got changed and had dinner at their amazing restaurant which has been awarded AAA five stars as well as Forbes five stars. The staff was incredible and it was a night I’ll never forget!

Saturday we wanted to get brunch, and headed back to Cape Porpoise as we heard great things about a local restaurant, Musette. The food was fantastic, but brunch got even better when we realized McDreamy himself, Patrick Dempsey, was sitting right across the restaurant from us! I had seen his signature on the wall at the Ramp, but never in my wildest dreams did I think I’d see him! He was enjoying breakfast with friends, so we didn’t bother him for a photo, but if he had been leaving at the same time, I TOTALLY WOULD HAVE.

We returned to Kennebunkport and wondered around the shops and cute little town for the afternoon. We stopped in Batson River Brewing for a few hours and enjoyed the local beer and food….and watched some of the Masters. It is in an old Victorian house and seemed to be very popular with the locals to enjoy the beautiful April day. We had dinner at The Burleigh, a local restaurant/bar in a hotel which was adorable and had a fantastic lobster pasta.

Sunday we slowly walked the town, as we had to get ready to depart. We hopped into a local bar, the Pilot House, to watch the final round of the Masters, and then we had to hit the road back to Boston to catch our flight. It was quick weekend getaway, but it was so relaxing, it felt much longer than it actually was!

I’d love to help you plan your next getaway, no matter how long the trip may be! Feel free to contact me here if you’re trying to plan a romantic or celebratory getaway!