Road-Tripping Up the Maine Coast: A 5-Day Itinerary

This month three friends and I took road trip up to Maine, where we hung out for five days! After California, Maine is the state that I’ve always wanted to visit, since I’ve heard such great things about Portland and the seaside up there, and it did not disappoint!

Itinerary and photos below the cut!

Day 1: The Road to Kennebunk

We drove up from New York City, which meant we got to stop at random places along the way! First we stopped at a Starbucks and got coffee, because what’s a road trip without a coffee run? About an hour later we got hungry, so we picked a random restaurant called Effie’s Place. We ate out on their patio and I had a delicious chicken salad. From there it was a mostly straight drive up to Kennebunk, where our Airbnb was. After settling in, we went out into town for an early dinner of lobster rolls at The Boathouse, a waterfront restaurant. After that, we drove to the closest beach and hung out for a while. It was chilly and there was no sun, so the beach was pretty much empty, which of course made it my favorite beach.

Day 2: Nature Trails, Farms, and Kennebunkport

We woke up very early the next day because I was determined to grab donuts from Congdon’s Doughnuts, a legendary doughnut place, and MAN, were those doughnuts incredible. Literally the best doughnuts I’ve ever had in my entire life. I would kill for those doughnuts. We didn’t eat them until after we had breakfast, though, and for breakfast we went to a cute little cafe called Brewed Awakenings, which, oddly enough, offered huevos rancheros, so I tried those for the first time in my life and loved them. They also had a spectacular iced mocha.

After, we stopped briefly at Douglas Harding Rare Books, a bookstore with a dizzying collection of rare books and maps, including out of print SFF novels. I didn’t actually buy anything, probably because I was very overwhelmed by the selection and didn’t want to keep my friends waiting too long, but I just loved being in there.

Then, we headed out to our next destination: the Rachel Carson Wildlife Preserve. We walked the Rachel Carson trail, a super short 1-mile trail (perfect for us lazy bums lol) that was absolutely gorgeous. Honestly, everything felt like I was looking through to a portal to another world. We also stumbled upon a group of elderly folks kayaking, who invited us to come along. Oh, and we also found a very creepy tree.

Our next destination was Snug Harbor Farms! They had actual ponies, a gorgeous meadow, a cute little shop, and just a very chill vibe. After that it was lunch at Mabel’s Lobster Claw, where I had a lobster cobb salad and blueberry pie (who knew Maine was famous for its blueberries? Not me).

Then we walked around Kennebunkport, a cute little town that I really should have taken more pictures of, and bought loads of candles for some reason, and blueberry jam. After that we headed on over to St. Anne’s by the Sea Episcopal Church. It’s right on the ocean, as the name would imply, and inside the church was so peaceful. It looked and felt ancient, which makes sense, considering the stone chapel has been in use since 1892!

Day 3: Portland

The next day took us to Portland, although we first stopped for breakfast at Joseph’s By The Sea, which had a lovely view, as the name would imply. Then we decided to forgo the GPS and drive up locally, which meant we ended up stumbling upon an absolute gem: a roadside ice cream shop that puts fresh strawberries on your ice cream, picked from the farm behind them. This is what I love about road trips — you’re always going to discover something fun along the way!

Before driving into Portland proper we stopped at the Portland Head Light, a famous light house. Then we set our GPS to the Duckfat Frites Shack, which is famous for its fries. Sadly, they were just…okay. I mean, they were fries, and they were good, but there was nothing special about them. After that snack, we headed over to Longfellow Books, a used bookstore where I purchased ALL ABOUT LOVE by bell hooks and an out-of-print used copy of MISTBORN by Brandon Sanderson. We walked around Portland for a bit and bought some stuff (Stonewall Kitchen is apparently based in Maine, so you bet I bought a ton of stuff I don’t need there).

Since by that point we were tired and close to being starving, we decided we’d just drive around for a while, which is how we discovered Fort Allen Park. We kind of just lay down on the lawn for a bit and enjoyed the ocean view. Then we headed over to the Highroller Lobster Company, where I spent an exorbitant amount of money for a meal that was only okay. Like, I had about eight lobster rolls on this trip, and this one, for all the hype, does not even make the top ten. Alas.

Finally, we left Portland and drove up to Bar Harbor. It was dark by then, and so we drove in the pitch black on country roads, which is my favored aesthetic, but my companions were slightly terrified. We made it safely to our Airbnb, however, and hit no moose or deer.

Day 4: Bar Harbor and Acadia

Since our Airbnb was actually in Seal Cove, we started our day with a 30-minute drive into Bar Harbor, where we ate a very hearty breakfast at the 2 Cats. Then we walked around Bar Harbor for a short time, and I bought books at Sherman’s, Maine’s oldest bookstore! I got A DEADLY EDUCATION by Naomi Novik at 40% off, a brand new copy of HOUSE OF HOLLOW by Krystal Sutherland, and a gorgeous copy of THE FORGOTTEN BEASTS OF ELD by Patricia McKillip!

Then it was off to Acadia National Park. Because it was a Sunday, the park was super duper crowded, so we didn’t spend too much time there. We did a tiny bit of the 27-Mile Loop — we stopped by Sand Beach, which was extremely crowded, so we left early, and then we stumbled upon some rocks jutting out into the ocean, where we sat for like an hour because it was cool and shady and we were the only people there, except for a rowdy seagull we christened Kevin.

Then it was off to dinner at West Street Cafe, which was actually one of my favorite places that we ate, but sadly I was so hungry I totally forgot to take a picture of my food. The lobster roll was top tier, though, as was the blueberry pie! After that we strolled around Bar Harbor a bit more. Funny story: I bought a really cool and colorful sweatshirt and ended up forgetting my iPhone in their shop! I had a momentary shock, but then my friend remembered I had shared my location with her, so we checked that, and then my other friend called the phone, and the shopkeeper answered, so all was well.

To end the day, we thought we’d check out the sunset at a random beach, and we tried to drive down there…only to realize our car would not make it (unlike the jeep in front of us), so we had to back out very carefully without running any people over. Some white dude came up to my window and was like “want me to turn the car around for you” and “are you sure you’re not gonna go down there? because if you are we all wanna watch.” He was just joking, but he sure was smarmy! The beach was nice, though, when we managed to get there on foot.

Day 5: More Bar Harbor and Acadia

Our last day! We set it aside for more time in Acadia and a two-hour sunset boat trip. Acadia was thankfully far less crowded on a Monday morning, so we enjoyed ourselves far more. We went on the 27-Mile Loop again and stopped at two or three places, including Jordan Pond. We sadly did not get popovers at the famous restaurant because it was just too crowded. After Acadia it was a lovely dinner at Stewman’s Lobster Pound!

And then it was the sunset boat trip! We booked this on a total whim but it ended up being an awesome way to close off the trip. It was freezing but gorgeous; we saw seals, puffin-like birbs, a cool lighthouse, and two deer just hanging out on one of the islands! We learned a lot about lobsters (apparently they’re cannibals) and lobster fishing and also that there are a lot of rich people who own cottages on the harbor (not surprising).

Day 6: Back to New York City

No pictures here because I totally forgot, but we had a great breakfast at a place called Josie’s Country Store and Cafe, which we stumbled upon because our intended restaurant had about a 30 minute wait and we were eager to get on the road quick, since we had an eight-hour drive ahead of us. But Josie’s turned out to be awesome! So then it was a drive down to Newburyport, since we’d chosen to eat at Michael’s Harborside in advance, for our very last lobster roll, which was delicious. And from there it was a straight drive into New York City!

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