Tuesday, September 15, 2015


As I mentioned in my packing post, Maine has been on my East Coast bucket list (and last summer of my 20s bucket list, too) for a while. While I can now check it off—I'm already more than certain that I must go back. Not since I first set foot in New York City have I fell so hard and fast for a city as I did for Portland, Maine.


If ever there were a bittersweet Labor Day Weekend, this was it. We celebrated the end of summer like it might never come again. After a slightly torturously long drive, we were lucky enough to get a stretch of days in Portland graced by high temperatures and plenty of sunshine. We gorged ourselves on lobster because of course we did. We drank indulgently, ate well and spent a lot of time out on the water. It was glorious, just a little bit gluttonous and rather unforgettable.


#1 EVENTIDE: Arguably the buzziest seafood spot in Portland, this place is so delicious I don't know what else I can say other than just go there and eat all the things—and order two brown butter lobster rolls for yourself. Just trust me, one will not be enough. Even outside of the realm of rolls, this was one of the most delicious things I've ever eaten. Additionally, the bluefin crudo and toro (one was a special but I can't remember which) are tops.

#2 THE CLAM SHACK (in Kennebunkport): After departing NYC around 8 a.m. and driving steadily north for about six hours, we ditched the highway, rolled down the windows and cruised into the picture-perfect coastal town of Kennebunkport. We parked in what must, for some reason, be the most adorable public parking lot in Maine, and walked across the bridge to the famous The Clam Shack for our first lobster roll of the trip. It did not disappoint. In fact, it recently won The Travel Channel's 'Food Wars' for Best Lobster Roll. Served on a round potato bun and dressed in your choice of butter, mayo or both (get both, duh)—it's a transcendent treat. Oh, and you have to get a $3 lemonade from the stand in front of the picnic tables. It's literally the best I've ever had.

#3 PORTLAND LOBSTER COMPANY: This place is right on the water, and the vibe by the outside bar is the kind of coastal-meets-laidback you'd hope to find on a harbor in Maine. Come here, grab a seat a picnic table in the shade beneath a string of buoys, then throw back a few local Shipyard ales while the band on the deck plays a little Van Morrison. The lobster roll is great, the crab cake is decadent and enormous, ditto the lobster mac and cheese.

{ Everything is right with the world when you've got a lobster roll in one hand, a craft beer in the other, friends all around and water all around your friends... }

#4 GILBERT'S CHOWDER HOUSE: We didn't dine-in here, but we did get bags and bags of lobster and crab rolls, chowder, fried clams and onion rings to go. When we finally settled in to eat them (on a boat in the middle of Casco bay, I'd like to brag) they were pretty damn good. We all agreed these were lovely but our least-beloved rolls of the weekend, so do with that assessment what you will.

*OLD SCHOOL WILD CARD* J'S OYSTER: This is the place to go when you're ready to forgo the roll and commit to a full lobster dinner—complete with steamers and an ear of corn. (Which you must do, by the way.) The vibe is local, a little divey, super friendly and pretty much no fuss. It is old school Portland and I highly recommend it. And, there's nothing quite so satisfying as ripping apart your dinner with your bare hands.


VISIT THE PORTLAND HEAD LIGHT: After eating and drinking most of the day away on Saturday, a few of us hopped in the car and headed to Portland's closest lighthouse, in the town of Cape Elizabeth. It is so quintessentially Maine—I'm not sure how else to describe it. The red and white building and iconic beacon are perched on a rocky cliff, and you can wander dirt paths through the lush, hilly park (Fort Williams Park) all around the area to see it from different and equally 'gram-worthy viewpoints. Go at sunset and prepare to be absolutely delighted. (Note that Fort Williams Park has a lot to see and do—picnic sites, a beach, forts to explore, etc.)

PADDLE OR KAYAK IN CASCO BAY: There are any number of places to rent kayaks and paddle boards around Portland; you can take a lesson or venture out on a guided excursion or simply rent something and head out on your own. We kept it pretty simple and rented boards and a kayak from Portland Paddle (which was on East End Beach, just down the hill from our charming Airbnb rental). We tootled around with some craft beers in our dry bag and created a Seafair-like floatilla so we could chill and take in the view and chat (and take precarious selfies, of course).

{ Jerry and jumped / dove into the frigid Casco Bay waters because, you know, when in Maine... }

TAKE A CRUISE: Hands down the best thing you can do for yourself in Portland is get out of Portland itself and onto the water. Whether you take a sunset cruise on Casco Bay Lines or happen to have a friend who has a rather large boat and nothing better to do on a Sunday afternoon—go see some of the 180+ islands that are scattered throughout the bay (and the many, many, thousands of lobster trap buoys that dot the water). If you're feeling brave, jump in the water!

{ Not far from downtown but just around the corner from our Airbnb, I started my mornings with a walk to the top of Munjoy Hill (Congress Street) to hit up Hilltop Coffee and the Hilltop Superette for iced coffee, pastries and fresh berries. This street has tons of cute shops, bars and restaurants, and even has its own lighthouse! }

{ Gang's all here! We got a little taste of the local nightlife playing darts at Amigos }

WALK AROUND THE OLD PORT: The Old Port area of Portland is where you'll find plenty of shops, tons of bars and trendy restaurants like Central Provisions. We had a drink at Novare Res—an awesome beer garden tucked away off the street—and had some stiff drinks and a round of late night darts with the locals at Amigos. Walk along the waterfront to see the working wharves with their piles upon piles of lobster traps, colorfully painted cabins along the docks and boats with names like Meghan and Deborah II.

DRINK ALL THE LOCAL BEER: Allagash. Shipyard. Rising Tide. We popped into Bier Cellar upon arriving in town and loaded up on cans bottles and more cans of all manner of beers from fancy sours to the easy-drinking Maine Trail Ale to a double IPA none of us actually liked that much, called Larry. If the weather isn't as glorious as it was over LDW (temperatures start dropping in September), you can brewery hop with the best of 'em on Industrial Way and still feel like you're soaking up the best of what Portland has to offer.

{ The scene at The Clam Shack in Kennebunkport was made all the more authentic with lobster trap tables and a kid selling golf balls for 50 cents in hopes of buying his own iPhone (using the trust system) }

{ Jerry and I were rather coordinated—I'm wearing my Madewell chambray shirt, an American Eagle bandana and those beloved white Birkenstocks }

CHECK OUT KENNEBUNKPORT: If you love tchotchkes and nautical things, you must take a spin through the quaint streets of Kennebunkport. About an hour south of Portland, this town is picture-perfect—like what Maine looks like in the postcards in your mind. Tiny ice cream shops, horse-drawn carriages, striped and anchor-printed everything—it's preppy overload, but with genuine roots. Don't leave here without some tacky-meets-timeless swag that your future children will wear and brag to their friends is "so vintage."

MAKE YOUR OWN LEMONADE: Okay so this is a thing you can do anywhere, but I was totally inspired by the stand at The Clam Shack, and I bet if you go, you will be too. I picked up a dozen lemons from the Superette, plus strawberries and a chunk of ginger. We plucked and then chopped a bunch of fresh basil from our Airbnb's garden, too. To make, combine 2 oz. (about a shot's worth) of fresh-squeezed lemon juice with about 2.5 cups of water, then add 3 generous tablespoons of sugar. Shake vigorously over ice, add chopped fancy ingredients to your taste, and then revel in #summerinaglass.

*Transportation for this trip was generously supplied by General Motors' Drive the District program—we cruised up to Maine and back in a 2015 Buick Encore.

*Many thanks for photos co-opted from Kyle and Jerry.


  1. Replies
    1. https://www.youtube.com/watch?v=HLI-nLPiaJA

      Oh how I miss those lobstuh buns

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