Eat Your Way Through Kittery: Great Food, Drinks Just 1.5 Hours From Boston

Where to go for food and drink in the gateway to Maine

Marc Hurwitz

New England’s largest state is perhaps its most diverse when it comes to things to see and do, as Maine certainly seems to have a little something for everyone. Here you’ll find rugged fishing villages perched on rocky ledges, deep forests that extend to the Canadian border, jagged peaks that challenge even the best of hikers, laid back beach towns and of course one of the most interesting small cities in America in Portland.

The first community that many encounter upon entering Maine is often lost in the shuffle, however, as Kittery is a long way from such destinations as Portland, Bar Harbor, Moosehead Lake, Mount Katahdin and Camden, so other than perhaps a quick stop for gas and restrooms, this little town across from Portsmouth, NH, often seems to be just another place along Route 95.

Kittery also has a reputation as being a factory outlet destination and little else, and indeed, so many people picture the place as the generic-looking stretch of Route 1 with lots of traffic lights and some shops with great deals, but Kittery is much, much more than that — especially when it comes to food and drink. Hidden among the outlets and also away from Route 1 on the back roads are some truly great restaurants, bars and food and drink shops, so much so that Kittery is considered, to some, one of the best dining and drinking destinations in all of New England.

Generally, the dining and drinking scene in Kittery can be broken down into two areas, with Route 1 being one of them. It may look like any other commercial strip in America, but this stretch of highway between Portsmouth and York has some really special places, including one of the best pizzerias in the Northeast in When Pigs Fly Restaurant & Pizzeria (460 US Route 1), which is located just north of the outlets.

When Pigs Fly, in Kittery. Marc Hurwitz

Most people know the business for its outstanding breads (and other treats such as doughnuts), and while the Kittery location indeed has a terrific bread store within the building, the restaurant next door features wood-fired thin-crust pizza that rivals such legendary New England spots as Regina’s and Santarpio’s in Boston and yes, even Pepe’s and Sally’s in New Haven. When Pigs Fly also features some terrific local beers including Bissell Brothers, so if you like pizza and a brew or two, this place will likely be heaven to you.

The pizza at When Things Fly Marc Hurwitz

Just down the street from When Pigs Fly is a place that lovers of burgers, hot dogs, and beer may want to check out, and the Maine Beer Cafe (439 US Route 1) is also an incredibly friendly spot featuring a gregarious owner who loves to chat with customers, while the rustic little space brings to mind the type of deep-woods watering holes that you might find five hours from Boston rather than only one hour up the road. The burgers here are thin flat griddled patties that are more common in California but which are making their way more and more to New England, while the mild pork hots bring to mind ballpark franks, albeit really good ones.

Maine Beer Cafe Marc Hurwitz

The beer list at the Maine Beer Cafe is every bit as impressive as that of When Pigs Fly, including beer from one of the best local breweries you’ve never heard of — Battery Steele, which is based in Portland and includes one called Flume which is a must for those who like New England-style IPAs .

Some good dining and drinking options can be found toward the southern edge of the outlets in Kittery as well, and if you’re looking for something a bit more serene and upscale, Robert's Maine Grill (326 US Route 1) is a good call, especially if you’re a big fan of all things seafood. This elegant spot is a bit of an oasis from the hustle and bustle of the outlets and is perfect for quiet conversation and a long, leisurely meal and even though it has an upscale feel, Robert’s is casual and not stuffy at all.

Robert's Maine Grill is a great call for seafood fans. Marc Hurwitz

Here you will find such classics as lobster rolls, clam chowder, steamers, and crab cakes, and the raw bar includes a wide variety of oysters that are harvested locally. Landlubbers are able to choose from burgers, steaks, chicken, and pasta, and wine and cocktails tend to take precedence over beers, though some good local brews are offered as well.

The lobster roll at Robert's Maine Grill Marc Hurwitz

For a more traditional clam shack type of place, Bob’s Clam Hut (315 US Route 1) may be more your speed, with such offerings as fried clams, shrimp and scallop baskets, burgers, hot dogs, tuna melts, fish chowder, lobster rolls, and fish sandwiches all being available at this roadside spot that has been around for more than 60 years.

By the way, if you’re a beer lover and want to take home some brews from Maine’s burgeoning local beer scene, Spruce Creek Provisions (290 US Route 1) is an under-the-radar spot where locals tend to go to and which features beers from Bissell Brothers, Battery Steele, Definitive, Austin Street, Lone Pine and so many others.

While the Kittery section of Route 1 has some excellent options for food and drink, heading east onto lesser-traveled roads will bring you to some beautiful oceanside areas, though much of it consists of residential and/or unspoiled areas with little in the way of commercial activity. The southeast corner of town, however, is where the two come together, with Kittery Foreside (which is also known as Downtown Kittery) being a quaint and scenic waterside community that is one of the region’s true hidden gems.

The heart of the district is Wallingford Square, a walkable commercial district with historic buildings, views of the sea, and local restaurants and bars such as Rudders Public House (70 Wallingford Square), a watering hole that you generally won’t read about in any tourist guides but is a place that gives a real taste of the Foreside via locals who hang out there. Comfort food is the name of the game at this friendly spot, with options including burgers, wings, fish and chips, chicken sandwiches, and something called the “Porky Pig,” which is a delicious sandwich consisting of pulled pork, cheddar cheese, and bacon.

Rudders Public House Marc Hurwitz

Across the street from Rudders is a quirky Asian eatery called Anju Noodle Bar (7 Wallingford Square), which offers such options as kimchi, pork bun, Vietnamese-style wings, cumin lamb noodle, miso ramen and duck yakisoba, and fans of sake will have several options to try here.

A short walk up the road from Rudders and Anju will bring you to the Black Birch (2 Government Street), a beloved farm-to-table gastropub that feels like it should be in Brooklyn rather than on the Maine coast (and yes, some people call Kittery Foreside the Brooklyn of Maine). Highlights at this little restaurant include deviled eggs, house-made sausage, poutine with duck gravy, seared scallops, and fried shortrib.

Finally, if you’re looking for lighter fare or something quick, head back down to the block housing Anju and hit up Lil’s Cafe (7 Wallingford Square) for a cruller, sandwich, a cup of coffee and maybe a loaf of bread to take home while soaking in the ambiance of this charming little neighborhood.

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