“We just love it here.” This is what realtor Ali Goodwin of Haven Homes & Lifestyle says she hears most frequently from clients discussing Kittery. Dubbed the “Gateway to Maine,” this historic, seaside town is full of quintessential Maine and artistic flair every hour of the day.
Mornings in Kittery are active and alive, thanks to working waterfront and Portsmouth Naval Shipyard commuters arriving early. She enjoys grabbing a breakfast sandwich and coffee from a local bakery on the way to her workplace, which abuts one of the big lobster companies. The sounds of boats starting up fills the air daily. “It’s a well-visited area,” she adds. “Unlike a lot of towns up the coast, everything here stays open year-round.”

As the day advances, lunch spots start to open their doors, and when the shipyard gets out in the afternoon, breweries begin to open as well. “In the evening, the night crowd and music come to life,” says Ali. “Kittery Dance Hall always has live music and events. Bars and restaurants have a certain evening flow. There’s something for everyone to enjoy.” For this reason, she claims evening, especially in the summer, as her preferred stretch of life in Kittery (“Though, can I say every time of day is my favorite?”). The region’s dining stands out for the intentional menus and sourcing of local ingredients. Be sure to get a drink at The Wallingford Dram before popping into the Buoy Gallery, tucking into a meal at Festina Lente, and ending the day at the Dance Hall to see a band.

Kittery is the southernmost coastal town in Maine, just across the river from Portsmouth, New Hampshire (hence the “Gateway” moniker). It also has the distinction of being the oldest town in the State of Maine, incorporated in 1647, well over a century before the birth of the United States. This means Kittery is the location of some of the oldest homes in Maine, such as the John Bray House, previously covered in Decor Maine. The town’s rich history has shaped its culture: Everywhere you go, you will find historical buildings, monuments, forts, and the shipyard. There’s even a park dedicated to Kittery’s history. “You are completely immersed in it,” Ali says. “Kittery stands out as so incredibly vibrant. You have all the modern amenities of a progressive town, and yet you can’t escape its historical charm.”


It’s no wonder the southernmost point of Maine’s 3,000 miles of coastline possesses a certain mystique that has lured city-dwellers for centuries. “From Kittery to Ogunquit, there’s a long history of artist colonies,” Ali says. “Surf Point is one such artist residency that attracts unbelievable talent.” Portsmouth’s close proximity also offers a host of galleries, museums, and historical societies laden with inspiration for the creative types.


Ali describes the town in four parts. First, Kittery Foreside, which includes Wallingford Square, the cultural center of town. “The Foreside smells like someone is baking something extraordinary at all times,” she says. “I’ll walk out of my office door and think, ‘Who’s got the garlic bread cooking?’” Second is Gourmet Alley, named for its specialty food shops and restaurants. Kittery Point is the third part, an area across the 103 Bridge, where you’ll find a majority of the oldest homes. The Rachel Carson Preserve and fantastic beach access are also associated with this section. The last area she describes is the northern section of Route 1, home to the Kittery Outlets.


The best part of living in Kittery? “Access to all of the amazing art, music, food, beaches, and trail networks is what makes this place special,” Ali says. “It’s a great option for people who want community without living in a big city. Portsmouth is just a short drive away, so it’s easy to get that city experience.” She also notes the town’s transformation over the past 15 years. “Kittery has gone through an incredible renaissance thanks to young entrepreneurs who have come to this place and opened exciting businesses. It’s become more attractive to both the people that live here and tourists alike.”
These qualities attract a diverse community. “People are a great resource in Kittery,” Ali says. “When you walk into Lil’s Cafe, it is always packed full of people. The fabric of the town is in there. Everyone coming together, getting ready for the day.” It’s no wonder why so many remark, We just love it here.