My best friend Mike and I share a love for Georgia O’Keefe, Americana and the great open road. After an ayahuasca-filled adventure through New Mexico last year, we opted for a more tame all-you-can-eat tour of Maine this summer. Also, I’m pregnant.

DAY 1:

Mike rents us a car…all the way in Jersey City. (Note to self: No longer put Mike in charge of renting cars). The adventure begins. We download In the Garden of Beasts on audible and onto I-95 we go.

The drive is long. How do you make it feel less long? Stop at Frank Pepe’s in New Haven. It’s a little out of the way – plus there’s an offensively long wait at peak hours – but tell me if you still care once you’re devouring White Clam pizza and a Margharita pie topped with roasted red peppers. Pro tip: Order 18″ and pack the leftovers to eat when you check into your hotel room in Kennebunkport at midnight (or was that just pregnant me?).

Speaking of hotels, I’ve never been so happy to see one as I was with The Kennebunkport Inn. It’s a little big inn – with more rooms than you’d think, right in the center of town.

DAY 2:

It’s time to no longer think in terms of traditional meals: There is no breakfast, lunch or dinner. There is only lobster.

On that note, we wake up and make our way to The Clam Shack when they open at 11. The order: Lobster rolls + Clam Chowder. Fun fact: It’s just called Clam Chowder here because it’s New England and there’s only one New England Clam Chowder. Duh.

Aside from The CandyMan, where I stock up on weird flavors of taffy like Root Beer Float and Key Lime Pie, the most exciting thing to do in Kennebunkport is to visit Walker’s Point, George H.W. Bush’s compound.

Following the map, Mike and I drove right up to his front gate before we were stopped by security and told to drive further along the road to a place where senior citizens were gathered admiring the 41st POTUS’ summer home.

Next up: Goose Rocks Beach. Stop for oysters/lobster cocktail (and a real cocktail) at The Tides Beach Club. Bonus: Eating there gives you parking access (otherwise it’s permit only near Goose Rocks Beach) and you can use their beach chairs, towels, etc.

Make the 2 hour drive to Camden.

We stayed at Lord Camden Inn (Mike found it…mental note to no longer put Mike in charge of hotels either though he would probably argue that it was fine). (Also, it is to be pronounced only with an English accent. “The Lowd Kem-Den Inn”.)

Doing it all over again, I’d stay in Lincolnville at The Lincolnville Motel instead of Camden; we drove to it the following day so I could check it out (I had read good things) and it was adorable. No frills (at all) but chic and clean and campy (sort of like Ruschmeyers in Montauk).

At this point, you may be worried that all of this lobster could lead to scurvy. Fear not – head to Long Grain for amazing Thai food. You will be very thankful for their steamed local kale and tofu which doesn’t sound delicious but it is.

Dessert is ice cream at Camden Cove.

DAY 3:

Drive to Portland.

The best thing you will do on this drive is to stop at Red Eat’s in Wiscasset. So cute, so yummy. Apparently on summer weekends the bridge traffic is terrible and everyone gets out of their cars to have lobster rolls while they wait to cross. If the line is too long (or if you just want to stock up on snacks for the car) check out Treats for cheeses, sandwiches and soups.

The rest of the village is adoooorable. Antique stores + home decor stores (Birch, Moulinette, Rock Paper Scissors) that are sophisticated and chic.

Get to Portland, finally, and have dinner at cool, casual Terlingua. It’s down south BBQ meets South America. There’s delicious tortilla soup and BBQ specials on the blackboard (we had the brisket, highly recommend).

Stay at The Press Hotel. It was OK – perfect enough. Good location. It would have been better if there were rooms with double beds – instead Mike ended up on an air mattress that deflated in the middle of the night. Eep.

DAY 4:

It’s a busy day of Portland activities (aka eating).

Start with breakfast at Dutch’s – an order-at-the-counter, seat-yourself, cafeteria-styled restaurant that reminds me of my childhood in Puerto Rico (complete with linoleum floors, faded booths and vintage travel posters) but home to an extensive, yummy menu of breakfast and lunch sandwiches.

Check out the Portland Museum of Art, skip Higgins Beach (it’s eh).

If you’re jonesing for some beach head to Crescent State Beach – it’s a state park but we found it to be really quiet with soft soft sand and calm water. Highly recommend picking up provisions from the nearby Cheese Iron (i.e. meats, cheeses, crackers, sweets, etc..) and having a picnic.

Stay for a bit and then continue on to Fort Williams Park in Cape Elizabeth to see the Portland Headlight lighthouse at golden hour. If the Bite into ME food truck is still open, it’s worth the scurvy.

Leave just before the sun goes down so you can catch a proper sunset up the road at Kettle Cove State Park. It’s the most beautiful, magical sunset in Maine, hands down. Bring a blanket and curl up to watch the show OR find out how to rent a paddle board nearby (there were people on them and I was very jealous).

Nearby (for before or after or both, no judgment) is Kettle Cove Creamery. It’s everything I ever wanted in an ice cream stand. Flavors like blueberry pie, salty chocolate malt and sea kelp (yes, it’s good) PLUS they had fresh soft serve, too.

Dinner: Central Provisions (James Beard finalist etc. etc.) on Mule Street. Also wanted to try Eventide but alas, too many restaurants not enough time.

DAY 5:

DONUT leave Maine before you do two things:

Grab yourself a sicilian slice snack from Slab and wait on whatever line there is at The Holy Donut bc seriously, holyyyy donuts (ps, they’re made of potatoes so they’re a little thicker and chewier than regular donuts and they have lots of gluten free options).

Drive home, diet for the rest of the summer.


Things I wanted to do but didn’t: wild blueberry picking, Acadia National Park (too far), go visit some of the little islands outside of Camden (we tried to do this last minute and got stuck on a very long ferry line and then found out there wasn’t a return ferry until the following day…not meant to be)

Articles that I found helpful: Eater’s “17 Essential Maine Lobster Rolls”

Things recommended to me that I wasn’t able to do:
Edge comb: Glidden Point Oyster Sea Farm – near boothbay / Maine Botanical Gardens – small shack with their oysters that you purchase and then they have picnic tables and all the tools to shuck. So fun. Can bring your own beverages and just chill/shuck your own.
Portland: Lucky Catch boat tour. Very cool. Got to learn about lobstering then purchase a lobster off the boat for $6-7 depending on size. They’ll either cook it for you at the restaurant next door (Portland Lobster Company) or if you have a place to cook it yourself you take it with you.

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