Kennebunkport Maine Winter Trip

I am heads down planning our anniversary trip to Kennebunkport Maine! A trip to Kennebunkport has been on our to do list for a while now! It started with an episode of Diners Drive ins and Dives where the Maine Diner appeared on the show. My husband and I are both foodies and when we travel, we love to find hidden gems. We were drooling as Guy took his customary big bite. Of course, we immediately googled, and that marked the birth of the idea of a trip to Maine, specifically Kennebunkport.

So it began…

Though we were initially attracted by the food, the history and beauty of Kennebunkport sealed the deal. The tales of multiple Native American raids, Sea Captain houses turned into bed and breakfast inns and the Wedding Cake House, lured us to explore beyond the walls of our computer. To be honest though, when my husband said let’s do Kennebunkport for our anniversary trip my initial reaction was, “it’s too cold!” The Caribbean girl in me screamed, “take me to the beach, any beach.” I warmed to the idea however, (no pun intended) at the thought of a romantic winter getaway to Paint the Town Red.  

Where should I Stay in Kennebunkport, Maine

Kennebunkport is a haven for visitors. There are soooo many gorgeous properties to choose from and they all seem to have a tale. It just depends on what you’re looking for!

The Kennebunkport Inn: The pictures of the rooms in this 1890 tea merchant’s mansion are to die for – especially the Thompson Suite. With views of the Kennebunk River and the Dock Square I think I’ve fond my home away from home. Added to that the igloos at their Burleigh restaurant have had my name on them since I first read about them.

The Boathouse Hotel: I love the views from this hotel. It’s located on the Kennebunk River and overlooks the harbor. The coastal and maritime décor speak to my heart as they remind me of home and the Caribbean. The prime location in Dock Square is also a win.

Waldo Emerson Inn: The décor of this Inn reminds me of home and warmth. It’s a historical inn with a rich history. My research showed that it was built in 1784 by a shipbuilder who inherited the land and original cottage from Waldo Emerson. Between its proximity to The Wedding Cake House and the stories of it once being a stop on the Underground Railroad I wanted to stay here.

Captain Lord Mansion: This bed and breakfasts boasts of being the only AAA 4 Diamond Award for bed and breakfasts in Kennebunkport. It is gorgeous with its canopied beds, and amazing reviews!! I kept going back to this site as I looked at my options.

The Seaside Inn: I love the beach and the sound of waves crashing, so the ocean views from this hotel sealed the deal. We decided to split our stay and spend two nights here too! This is the only inn directly on the Kennebunk Beach. It is also the oldest family run business with its 9^th generation inn keepers. I can’t wait to explore the oldest inn in the US. Interestingly too, he is taking me to the beach! I did say any beach, didn’t I?

What should I pack for Kennebunkport, Maine

Of course, I’m writing this just as the Polar Vortex has turned the Midwest into a freezer! Brrrr…. So, warm clothes are top of mind. My packing list for Kennebunkport has all things warm! The theme is layers, layers, layers.

Thermal underwear? check? And of course, I’m throwing in some warm wool socks and wool tights… albeit cute ones.

Double check for the warm jacket and a couple chunky knit sweaters too!

I’m also taking a couple shirts for layering.

For this trip I’ll be living in my jeans paired with cute boots. Don’t be surprised if I layer dresses and skirts over my jeans! HA! I stay on team overdressed.

Snow boots are a must as I would love to experience the ‘Snow Stroll’ at the Mousam River Wildlife Sanctuary.

Where to eat in Kennebunkport, Maine

My husband and I are both love good food, so we can’t wait for our taste buds to waltz with the lobster rolls and clambakes of Maine. After all this trip was inspired by a food show! Ha! From our research these are the spots at the top of our dining list!

The Burleigh at the Kennebunkport Inn. I’m excited to experience their new outdoor igloo’s which look fun and whimsical. An igloo for two please! I like that they also have an electric fireplace. 

Old Vines Wine Bar: This is touted as a nightlife hotspot and the Old Vines menu looks delicious! Foodie alert for sure!

Pearl Kennebunk Beach: I’m excited to taste the award-winning chef, Rebecca Charles!! She hails from New York and brings her east coast menu to Kennebunkport with her famous lobster rolls and other culinary delights.

Alisson’s Restaurant: A little birdy told me that this restaurant is a staple for visitors and locals alike. I’ve found that if the locals eat there that’s where you want to be! Alisson’s has classic pub fare and has an impressive selection of local Maine beers on tap.

Batson River Brewing & Distilling: This restaurant is relatively new. I like the set up as a tasting room however featuring light bites and an amazing game room on the second floor. It has comfy leather couches, a shuffle board and board games. I’m stoked at the idea of the fire pit outside!

Have you ever been to Kennebunkport, Maine? Do share some of your tips if so!