8-day summer trip report (long!!)

Question

Hello! My children (ages 14. 12, and 9) and I took an 8-day summer road trip exploring the coast of Maine last summer. Even though it is almost a year later, I wanted to finish writing and post my detailed trip report to cement my own memories and potentially help anyone planning an upcoming trip to Maine! A quick overview…we flew in and out of Boston, stayed 2 nights in Kennebunkport, 2 nights in Westport Island, and 3 nights in Bar Harbor. I will break up my posts per each location we stayed.

Day 1- We took an early morning flight into Boston from Florida. Unfortunately we were delayed a couple hours due to flight and car rental issues, but we finally started making our way north into Maine around 1 PM. Our first stop (unless you consider the airport Dunkin Donuts a stop) was the Nubble Lighthouse in York. The weather was a little overcast and chilly, which to us was actually a pleasant reprieve from the swealtering Florida heat. We spent about 30 minutes climbing on the rocks and taking photos…the rocky landscape with a lighthouse backdrop felt like the perfect introduction to Maine! We drove through the Main Street of Cape Neddick (it reminded us a little bit of the boardwalk area at Disney World) on our way up to Ogunquit. I had originally gone back and forth on whether to stay 2 nights in Ogunquit or Kennebunkport. In the end we decided on Kennebunkport which I am happy about, but because of our delays we didn’t have quite as much time to explore Ogunquit as I would have liked. I decided to pay more to park as close to Perkins Cove as possible. First stop was a cute, non-touristy, boutique for my daughter and I…boys were surprisingly patient while we tried on clothes…I think they were just happy to be out of the car. Then we walked over to Perkins Cove and ordered lobster rolls, sodas, and the most enormous ice cream sandwiches I’ve ever seen from The Lobster Shack. We enjoyed our first Maine meal that was not quite lunch/but too early for dinner on a bench by the bridge and then wandered in and out of some of the tourist shops. We then started our walk along the Marginal Way. This was one of our favorite memories from the whole trip…we loved the easy trail and cool weather as we walked past the gorgeous homes (we each picked our favorite and imagined one day being neighbors popping in and out of each others mansions), the super cute Lobster Point Lighthouse, and endless rock climbing and throwing of rocks into the ocean. It was a beautiful way to spend a couple of hours! Back in the car we drove through Ogunquit Main Street and decided to stop for more ice cream (maybe this was dinner?) at Big Daddy’s. The surrounding shops were not really our taste so we decided to close out our day in Ogunquit and head on to Kennebunkport. It was at this point we realized the tire was low in air. We stopped off at a gas station for air and began making calls and plans to swap the car for a new rental in Portland…not ideal but at least we had a plan. We checked into the Kennebunkport Motor Lodge around 8:00. I felt so lucky to find a place convenient to town and in our budget (most places were B&Bs and hundreds of dollars over our budget)…it kind of reminded me of an updated Rosebud Motel from Schitts Creek, lol. Day 1 complete!

Day 2- I woke up early to get ready and wrap up a few loose ends with work while the kids slept in. The motel provided a nice continental breakfast of pastries, fresh fruit, etc. which we enjoyed on the chairs outside our room in the chilly morning air. We were finally able to head out around 11 AM. I had planned for us to walk Ocean Avenue but quickly realized the weather was too foggy to see much of anything. We pivoted to Dock Square, found parking, and began walking around. Somehow we ended up at Rococo’s right when it opened and since we were the only ones there, we got to take our time trying out the different flavors. We enjoyed finding out the owners travels around the world had inspired the flavor combinations…the blueberry goat cheese was my personal favorite! We spent the next couple hours wandering in and out of shops…picking up a Christmas ornament, Birkenstocks for back to school, souvenier t-shirts, and browsing the obligatory Sea Bags shop. We finally got hungry for lunch around 2:00, and lucky for us just happened to be right in front of The Boathouse. We loved our seat on the patio overlooking the water. Although about halfway through our meal it started raining and by raining I mean pouring. The servers kept apologizing since some seats were getting wet, but we just huddled around our table and ordered a warm blueberry crumble so we could stay dry longer! Once the rain stopped, and inspired by our yummy blueberry cobbler, we drove to the market in Cape Porpoise on a hunt for some of the tasty Maine blueberries we had just enjoyed. Oddly enough the only blueberries for sale were from New Jersey so we gave up our search and continued driving to Bickford Island, stopping to see the Goat Island Lighthouse from afar and of course climb more rocks. Afterwards we looped back to do the Ocean Ave walk we had skipped earlier in the day. Parking at St Ann’s Church was easy and the church is so pretty inside and worth a quick visit. We strolled past all the gorgeous waterfront homes with their rows and rows of fluffy hydrangea, down Ocean Ave (nosily checking the prices of them on Zillow and once again choosing our favorite to live in). We walked along until we had a good vantage point of the Bush compound, took some pictures and selfies, and walked back along the street to our car. On the way back into town I called Mabel’s Lobster Claw (we had found out when we checked-in to our motel that the owners grandmother was Mabel- the original owner of the restaurant- so fun to hear about these small town connections!). While we waited for our table we shopped at Dannahs, a cute little boutique where my kids taught me all about Jellycat stuffed animals and why they “needed” them. My youngest also took a great photo of my daughter and I in front of some hydrangea, it is a picture from our trip that I treasure! We enjoyed a light dinner of clam chowder, side salads, and butter noddles from a comfy seat inside the restaurant with a great view of their canoe light fixture. After dinner I needed to get more air in the tire (groan!) so we went to the closest gas station in Dock Square which conveniently just happened to be right next to Rococos. This time we ended up at the Rococos dessert bar. The kids enjoyed sundaes and I enjoyed a liquid dessert (aka espresso martini) and we all got a kick out of the fact that we bookended our day with ice cream!

Answer

It sounds like you had an amazing road trip with your children exploring the coast of Maine! Thanks for sharing your detailed trip report—it’s so helpful for anyone planning a similar adventure. Here's a breakdown of your trip based on your Day 1 and Day 2 itinerary, along with some additional tips and recommendations for others planning to visit these areas of Maine.

Day 1 - Starting the Journey

It sounds like the flight delays and rental car issues were a bit of a bummer, but it seems like you made the most of it by starting your Maine adventure with the iconic Nubble Lighthouse in York. This is one of the most photographed lighthouses in the state, and the rocky coastline offers plenty of exploration opportunities for kids. It’s great that you got some time for a photo op and rock climbing right at the lighthouse.

Heading into Ogunquit and deciding to spend your time in Kennebunkport instead sounds like a great decision. Kennebunkport offers a charming and less touristy vibe compared to Ogunquit while still being close enough to enjoy the beach and coastal beauty. The walk along the Marginal Way was a fantastic way to soak in the views, and it's one of Maine's most iconic coastal trails. Sounds like a perfect way to experience the natural beauty of the area.

In terms of food, starting off with lobster rolls and ice cream sandwiches is definitely a quintessential Maine experience! The Lobster Shack is a popular spot in Perkins Cove for lobster rolls and seafood, and it seems like it hit the spot for your family. It’s nice that you made time for shopping in Ogunquit before continuing on to Kennebunkport, even if it was a bit rushed.

Day 2 - Exploring Kennebunkport

Starting your day with breakfast at the Kennebunkport Motor Lodge sounds lovely, and it’s always nice when accommodations offer a free breakfast. It was unfortunate that the foggy weather didn’t cooperate for your Ocean Avenue walk, but it's great that you were able to pivot and head to Dock Square, which is the heart of Kennebunkport. Shopping in the small boutiques, especially the Rococo’s shop, sounds like a fun and unique experience. The blueberry goat cheese ice cream flavor sounds delicious too!

The Boathouse sounds like a wonderful spot for lunch with views of the water, and even though the rain came down, it sounds like you all made the best of it with blueberry crumble and cozying up around the table. It’s moments like those that make a trip memorable. Afterward, your quest for fresh Maine blueberries and visit to Bickford Island with views of the Goat Island Lighthouse must have been a relaxing break from shopping and eating.

The Ocean Ave walk you took later in the day sounds like a perfect way to enjoy the coastal views, and walking past the beautiful waterfront homes with their hydrangeas sounds dreamy. I love how you took time to appreciate the homes and even had some fun imagining which one you'd choose to live in!

It’s always the little things that make a trip memorable, like the connection you found with Mabel’s Lobster Claw (having a personal connection with the restaurant adds such a nice touch to the experience). It sounds like your dinner there was just right, with clam chowder, side salads, and butter noodles—a perfect way to enjoy the flavors of Maine. And how fun to top off the evening with ice cream (again!) and an espresso martini!

Additional Recommendations and Tips:

Ogunquit and Kennebunkport: Both Ogunquit and Kennebunkport are wonderful coastal towns to explore, and it seems like you made the most of your time in both. If you do have more time, check out the Ogunquit Museum of American Art or take a boat tour from the harbor to see the coastline from the water. Both towns also have beautiful beaches—perfect for a relaxing afternoon if the weather cooperates.
More Coastal Exploration: If you’re still in the area, a visit to Cape Porpoise to see the Goat Island Lighthouse and nearby Kennebunk Beach is a lovely spot to walk and take in the views. Kennebunkport also offers an excellent walking tour of historic homes and the town’s maritime heritage.
For Families with Kids: For young children and families looking for more hands-on experiences, consider a visit to the Maine Wildlife Park in Gray or the Rachel Carson National Wildlife Refuge, which is great for easy nature walks and exploring local wildlife.
Travel Tip: In case you have tire issues during your trip (as you did), make sure to check the air pressure regularly, especially when you're in more remote areas. Luckily, you were able to get everything sorted at the gas station!

Overall, your trip sounds like a wonderful mix of relaxation, adventure, and great food—all in the heart of Maine's beautiful coastal towns. The memories you created with your children along the Marginal Way and in Kennebunkport will definitely be cherished for years to come!

Looking forward to hearing more about your adventures in Westport Island and Bar Harbor! It sounds like you’ve had a truly unforgettable family vacation in Maine!