Eat New England

Beyond Bread: When Pigs Fly in Kittery, Maine, Is a Pizza Lover's Paradise

The pizza here is at such a level that some within the restaurant industry mention it in the same breath as Pepe's, Sally's and Modern in New Haven

Pizza at When Pig Fly in Kittery, Maine

One of the hottest communities in New England for dining is Kittery, a seaside town at the southern tip of Maine that's only about an hour from Boston.

Kittery is one of those places that has been "discovered" of late, as the Kittery Foreside/Wallingford Square area feels like a little piece of Brooklyn, New York, with offbeat restaurants, cozy bars and terrific food shops along with charming old homes and commercial buildings, some of which look out over the ocean.

The nearby stretch of Route 1 that's home to the Kittery Outlets has always been a popular place, and it now has new eateries mixed in with the longtime restaurants -- it has traditionally been known for its outstanding seafood spots.

Traveling to Kittery can cause a nice problem: there are simply too many options for food in both Wallingford Square and around the outlets. To make things even more difficult, if you head north of the outlets you'll quickly escape the hustle and bustle of Kittery as you head toward York, but some never make it there, because along this quieter stretch of Route 1 is one of the best pizza spots in all of New England -- and its name may throw you, because when people hear "When Pigs Fly," many think of bread and bread only.

Yes, the bakery sells its bread at supermarkets across New England, as well as at its three stores in the Boston area (Jamaica Plain, Brookline and Somerville), plus ones in Newburyport, Massachusetts, and Freeport, Maine. But the Kittery location of When Pigs Fly is all about the pizza, and so much more besides.

Inside When Pigs Fly in Kittery, Maine
Inside When Pigs Fly in Kittery, Maine

Housed in a sprawling space that had once been home to a beloved Christmas tree farm, When Pigs Fly Pizzeria consists of two sections. To the left is the company store, which is basically a bread shop that also sells everything from donuts to muffins to olive oil and more, and to the right is the restaurant itself, which has room for more than 150 people inside and (when the weather is nice) many more on the grounds out front.

The interior of the restaurant includes a small bar, an enclosed farmer's porch, a back deck and plenty of well-spaced seating, throughout which you may be able to catch a glimpse of pizzas being cooked in the wood-fired ovens along the back wall.

By the way, the outdoor space was created with COVID in mind, and was a marvelous spot this summer and early fall, as the tables were spaced very far apart. On a warm, sunny day, it seemed to be in some ways the best option here, especially for those who still aren't comfortable dining indoors.

The patio at When Pigs Fly in Kittery, Maine

There's a reason why so many people come here for the pizza pies. Wood-fired pizza is often something special, but when fresh, high-quality ingredients are used as they are here, the pizza is transformed into something almost otherworldly. The char on the crust from the high-oven temperatures imparts an almost rustic flavor to their Neapolitan pies, while the use of mozzarella and romano on many of their red sauce pizzas, even more cheeses used their white pizzas, and their wild mushrooms, house-cured meats and fresh veggies raise these pies to another level.

One highlight at When Pigs Fly is the humble pepperoni pizza, which is anything but basic, as the slices of meat are huge, covering most of the top of the pie. That wild mushroom pizza is so delicious that even people averse to mushrooms may quickly change their minds.

Mushroom pizza at When Pig's Fly in Kittery, Maine

It's nearly impossible to go to When Pigs Fly in Kittery and not get their pizza, but the restaurant has a lot more to offer than that, and it may be wise to plan for a multi-course meal of sorts, including appetizers and dessert.

Take the Brussels sprouts for instance; this lowly vegetable that many avoided at all costs growing up has been transformed here, flash-fried with a perfect amount of char and served in a savory ginger and sesame sauce that's so tasty it could almost be good enough to eat on its own. The hand-cut fries are another standout, served with ketchup, dijon mayo and spicy mayo, and the buffalo wings rival some of the best at various Boston-area bars.

Brussels sprouts at When Pigs Fly in Kittery, Maine

The desserts are always changing at When Pigs Fly, but a couple of standouts include the brownie sundae and the ice cream cookie -- they once had something called a "cookie trio" that hasn't been seen in a while, but if it ever returns, you'll want to be sure to save room for it.

Maine reportedly has more breweries per capita than anywhere else in the country.

It's a not-so-hidden secret that Maine now rivals Vermont when it comes to top local breweries, and When Pigs Fly showcases some of the best of the best in the state, making it extremely tough to decide which beer to order. Depending on the day, you might find options from Bissell Brothers, Oxbow, Battery Steele, Definitive, Marsh Island, Mast Landing, Maine Beer Company, Fore River and Allagash, along with others from New England and beyond. And if it's a cocktail you want, the restaurant makes some good ones, including great takes on margaritas, martinis, sangria and old fashioneds.

Beer at When Pigs Fly in Kittery, Maine

Kittery has nearly every kind of restaurant imaginable within its borders, and while many come here to get classic Maine seafood, while others come for their trendy eateries and local watering holes, it's tough to visit this wonderful old town and not go to When Pigs Fly Pizzeria. The pizza here is at such a level that some within the restaurant industry (and the local media) mention it in the same breath as Pepe's, Sally's and Modern in New Haven, Connecticut, even though it's a much different kind of pizza.

But it shows just how good the pies are at When Pigs Fly, and why some drive to Kittery with just this restaurant in mind, and everything else to see in town being just a bonus.

When Pigs Fly, 460 U.S. Route 1, Kittery, ME, 03904.

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