Of all the towns in the Seacoast region, Kittery is a “sleeper” pick for the next best small town in the area with around 10,000 residents. It has always been the younger sibling to Portsmouth, but in recent years, the Kittery Foreside area has become a bustling, cultural mecca in the Seacoast region. This seaside town’s emphasis on everything local—from food, arts, music, homes, and outdoors—makes it truly unique. Kittery hosts the annual Kittery Block Party in June, kicking off summer in the area. Kittery is home to the Portsmouth Naval Shipyard, Badger’s Island, the Isles of Shoals, & Forts Foster and McClary. It also is home to the Kittery Premium Outlets, Chauncey Creek Lobster Pier, and Pepperell Cove Restaurant & Marina.

Walking, Biking or Driving

With Memorial Bridge connecting Kittery to Portsmouth, Kittery Foreside neighborhoods are walking distance to all of downtown Portsmouth. There are biking trails along the Eastern Trail as well as a scenic, rolling hills, coastal drive or bike ride along Route 103 through Kittery and Kittery Point. Route One is the main road running through Kittery. It extends from Memorial Bridge, along State Road, through the Kittery Traffic Circle and heads north through the Kittery Premium Outlets. Traffic only exists on Route One on Sundays through the summer months, with virtually no traffic elsewhere throughout the area.

The Scene

Kittery has a vibrant local scene and a tightly-knit community that is evident at its annual Kittery Block Party. There is something for everyone: authentic restaurants (i.e. The Black Birch, Anju, Tulsi, Loco Cocos, Bob’s Clam Hut & When Pigs Fly Pizzeria), prohibition style cocktails (The Wallingford Dram), breweries (Tributary), local music and dancing (The Dance Hall), boutique and outlet shopping, local meat and vegetable markets (Carl’s & Golden Harvest), kayaking, paddleboarding, yoga, lobster houses (Chauncey Creek and Warren’s), art, fishing, and beaches. Seapoint Beach is residents only, and Fort Foster and McClary are nearby, with beaches, playgrounds, historic trails and landmarks. Young families are on the rise in the area, and there is a steady military family presence as the Naval Shipyard is there. The school system is improving, and will most likely continue to improve with the rise in families moving to the area. Property values are rising quickly and homes generally don’t last long on the market. It is also only an hour from Boston and 45 minutes from Portland, so commuting to a job or taking a day trip is an option as well.


Kittery was formally founded in 1647, and is the oldest incorporated town in the state of Maine. It was named after the birthplace of one of its founder, Alexander Shapleigh, who was born in the manor of Kittery Court in England. Together with the Pepperell family, fisheries were created along the river and Isle of Shoals. Fort McClary protected the settlement along the river. During the American Revolution, the first ships of the U.S. Navy were constructed on Badger’s Island, the small island bordering the Piscataqua River, across from Portsmouth. Then, subsequently the U.S. Naval Shipvard was established in Kittery on Seavey Island. From there, population slowly increased with naval shipyard workers taking up residence in Kittery.