Over Memorial Day weekend my fiancé and I road tripped to Kennebunkport, Maine. Each Memorial Day we like to plan something that is a bit of a drive so we can explore some more of what is close by to us. This trip was a bit out of the ordinary as it started with some car issues, but when we finally got going, we had the best time. Maine has always been on my list so I couldn’t wait to see what was in store.

Because we started out late on Friday night, we wanted to get as far as we could without taking a break. Our first stop was in Westport, Connecticut at Bartaco. Oh my gosh, this place was so good! The wait staff was super accommodating as we came in just before closing. Of course, I couldn’t say no to the Bartaco margarita, freshly squeezed right in front of me. We split the cauliflower rice bowl and some tacos. This place definitely hit the spot.

Because it was so late, the last thing we felt like doing was paying for a hotel room to sleep for a few hours. We picked a rest stop in Connecticut and decided to spend the night in our Mercedes Sprinter van on an air mattress. If you’ve ever been in one of these, you will know how lovely they really are. And if you ever get the chance, say heck yes to sleeping in one. All a part of the road tripping experience!

Our next stop was in Boston, Massachusetts. What a beautiful city! I was there many moons ago, so I didn’t remember much. We weren’t planning on stopping here, but when I saw how close it was to where we were, I knew we had to. The city is clean and beautiful with so much to do. I ended up picking OAK Long Bar + Kitchen located in Fairmont Copley Plaza for brunch. The cinnamon monkey bread and skillet mash were to die for. The perfect balance of salty and sweet. The ambiance here is just stunning. We picked the loveseat at the bar and enjoyed the scenery. I had read some reviews that it was more on the fancy side, but we felt that it was just right.

I wished we had more time to explore Boston, but I know we will be back some day. The next destination was Portsmouth, New Hampshire. This is worth the stop! We were full from brunch so we decided to do some shopping and stop for a drink. The Fresh Press had an organic activated charcoal juice that was right up my alley.

The houses are so charming; exactly what I pictured New Hampshire to be. We had gorgeous weather that day.

We stumbled upon Earth Eagle Brewings and enjoyed a flight of beer. I went with a local flight, the flavors were very unique.

There are so many cute shops and restaurants to enjoy. I kept wishing we could do it all. A little pick me up at Profile Coffee Bar and off we went.

A quick picture of the water as we left New Hampshire.

Now onto our final destination! I had read how great the antique shops were on Route 1 so we picked one to stop at. It was a good choice as a couple had just purchased the entire building and its contents. Literally, everything I picked up was 5$. We then made our way to The Cottages at Cabot Cove where we stayed in the Tranquility Cottage. To call this sweet little place adorable would be an understatement. I couldn’t have chosen a better spot. The staff here was extremely welcoming, we felt right at home.

I kept joking that if we were any taller we wouldn’t have fit! Beautifully decorated and full of charm. Each morning they would deliver breakfast to our door. What more could you ask for?

I had done my research so back when I was planning this trip, I booked a reservation for dinner at Earth at Hidden Pond. It is difficult to get in if you wait to book. Especially because we were coming shortly after they reopened for the season. I cannot even begin to explain how gorgeous the property was. It was like a fairy tale when we arrived at Earth. The restaurant is stunning and so unique. I am still dreaming of the lobster pasta. It was out of this world. There was a snap pea in my cocktail of choice and donuts on the menu, I was completely sold.


After dinner, we stepped outside to look around and finish our cocktails. We were surrounded by fire pits and comfy chairs with fluffy blankets. Just Heavenly. I wish my pictures had turned out but it was too dark at that point. I guess, you will have to plan a trip for yourself to experience just how enchanting it really is.

We stopped at Old Vines for a nightcap. The drinks are delicious with a fun atmosphere. We spent some time inside, and then made our way out to the toasty fire pit outside. Maine had so many fire pits, it was wonderful.

We had brought our tandem bike with us in hopes of using it to see more rather than just driving everywhere. There was one day we go to use it, as the rest of the days were rainy and overcast. I planned accordingly, with my Hunter boots.

We did some exploring of Kennebunkport on our bike and find quite a few shops. Daytrip Jr. was the perfect place to pick up souvenirs for my nephews. Loaded with outfits, books and gifts, there was something for every tiny person. The Deep Blue had a plethora of handmade goodies and the shop owner was so nice!

I had read that Snug Harbor Farm was a local garden shop that was pretty magical. I didn’t go to Maine to buy any garden gear, but I was ready to see something magical. Exotic birds, beautiful plants, and a gift shop with so many things unique to Maine. This is worth the trip.


Portland, Maine was a short distance from where we were staying. This city has so much to offer that we ended up exploring it for two days. Blake Orchard had delicious fresh pressed juice that actually stayed fresh until I was home in Pennsylvania. Shipyard Brewing is a great local brewery to stop and enjoy a flight. Aracana is a sweet yoga studio with beautiful items to heal your body and soul. The Holy Donut, with the fresh vanilla bean donut right out of the oven….if you turn onto the street, and see the line from where you are, trust me, just wait.

Central Provisions was a must for a cocktail. We had hoped to stop for lunch, but it was packed so we ended up downstairs, which was completely fine with us. We did go back the next day and enjoy brunch here.

Eventide Oyster Co. for the infamous lobster roll was the best choice we could’ve made. The lobster stew was something that I doubt can ever be replicated elsewhere. The curried carrots are also a must-have.


I bought a really cute and durable handbag at Rough & Tumble.

My Hunter boots were the perfect item to pack for my trip to New England. And it didn’t hurt that my initials were there for the perfect photo op.

Allagash Brewing, Austin Street, Battery Steele, D.L. Geary Brewing and Foundation are on the drive back from Portland to Kennebunkport. This industrial complex filled with great breweries is a good stop if you love local brews, Battery Steele was our favorite.

On our way home we stopped at Farm + Table in Kennebunkport. It is the quintessential shop to pick up some local goods. A friend had suggested that we stop at The Clam Shack for another lobster roll and the lobster dinner. The lobster dinner was worth every penny. Rococo had some delicious unique ice cream flavors. The Ramp was a great stop for chowder and a cocktail. 50 Local is a delicious farm to table restaurant that I would also recommend.


On the final day of our trip, we got up early and drove to the coast nearby our cottage. One last stop for breakfast at Boulangerie in Kennebunk and then it was time to start the drive home.

New England, totally road trip worthy.