How to Eat Your Way From New York City to Portland, Maine

Whether I’m home in Brooklyn, running around Caribbean cities or traipsing through Europe, my only real concern is where to eat and drink. I wish I could tell you that I have other hobbies, but I don’t. What you read is what you get.

One of the perks of this lifestyle, of course, is that occasionally really good opportunities arrive in my inbox. Few could beat Chevy getting in touch with me this past summer to ask whether I’d be interested in driving one of their 2017 Cruze Diesel cars from New York to Portland, Maine, with a stop in Boston along the way, aided by Roadtrippers. How does one refuse such an invitation? I couldn’t, anyway, and so for Labor Day, I mapped a route from Manhattan to Maine that would have my partner and I hitting some key stops along the way. From New Haven pizza to mashed potato doughnuts, here’s how to go on a stuff-your-face road trip that also provides some lovely scenic views.

Frank Pepe’s of New Haven
As a Long Islander, I have a special affinity for pizza and like to taste the varieties wherever I go. After hearing nothing but praise for the New Haven style, I was thrilled to get a chance to try it, and it didn’t disappoint (though I prefer my pie a bit saucier). Don’t skip this classic, no-frills family joint, especially during tomato season.

Matunuk Oyster Bar
They farm their own oysters here off the dock, and the view provides a great sense of Rhode Island’s quiet, beachy beauty. The freshness is unparalleled, so even if you’re still full from pizza, you’re going to enjoy yourself.

Fortnight Wine Bar
On your brief pass through Rhode Island, don’t miss Fortnight Wine Bar (a workers’ cooperative) where they might warn you away from ordering strange orange wines. The menu is written in chalk without any tasting notes to guide you, which requires either more back-and-forth with the bartenders or an openness to drinking something totally bizarre. Both are recommended experiences.

B&G Oysters
Because I read Barbara Lynch’s Out of Line: A Life of Playing With Fire earlier this year, I had to visit one of her restaurants while in Boston, and B&G won the race, as I could most vividly recall her experience of opening it with her sommelier. The small space provides a casual experience with exquisite food—the best kind of restaurant, as far as I’m concerned, and even better for a late Saturday night reservation.

Trillium Brewing Company
I have a new, half-joking aspiration to be a “beer bro,” and so one of my friends highly recommended a visit to Trillium Brewing Company. Their Citra Free Rise Saison was a gorgeous sip, and when you’re only in Boston briefly, this is undoubtedly the brewery to hit up.

The Honey Paw
There was a restaurant in Portland, Maine, that gave us an estimated four- to five-hour wait on a rainy Sunday night. It will go unnamed. The Honey Paw, though, provided. This mapo dofu was a mouth-numbingly spicy dish, a great follow-up to the scallion pancake and wok-charred eggplant. And for dessert? Caramelized honey, honeycomb soft-serve and chocolate shell. Never mind those five-hour waits.

When a bar is your kind of place, you can sense it before you walk in the door. That’s how it was for me and Portland, Maine’s MAPS, a globe-filled and dimly lit spot with a nice beer and wine list. Pulp’s Different Class played as I walked down the stairs into the bar and ordered a Stillwater Artisanal Shoegaze. There’s no sign to tell you this, but the jukebox is free, and its tiny selection of dark ’80s new wave and classic rock will perhaps provoke a war of passive aggression between patrons, but it’s all in good fun. Everyone should just let the bartenders play vinyl, anyway; their taste leaves nothing to be desired.

The Holy Donut
You will find a line outside this doughnut shop, but that’s because they’re really good and really weird. They’re not made with potato flour, which would likely be your first thought upon hearing “potato doughnut,” but actual mashed Maine potatoes. There are vegan and gluten-free options, too; everyone will leave happy. Skip the coffee, but don’t overlook the blueberry doughnut.