Town of Kittery, Maine

Located at the very tip of southern Maine, Kittery is the town you’ll land in once I95 carries you over the imposing arch of the Piscataqua River Bridge from Portsmouth, New Hampshire. While certainly not a twin to Portsmouth—Kittery’s hip, reimagined geographical counterpart across the river—this former fishing town has an appeal all of its own, drawing folks from all over the country with its maritime history, New England charm, and formidable shopping mecca. (And if you are one of those folks misled into thinking Kittery is only good for outlet shopping, read on and allow us to change your mind.)

Exploring Kittery Maine

Heading north over the Piscataqua River, if you glance to the east, you will see two other beautiful bridges spanning the river: The Sarah M. Long and the Veteran’s Memorial. Just past the Memorial Bridge is the Portsmouth Naval Shipyard—which, we must add, is a misleading name, as it is actually located on Seavey Island in Kittery. Shipbuilding eventually eclipsed fishing as Kittery’s main source of commerce, and the Naval shipyard is still active today. If you are interested in maritime history, set aside a day to hit Kittery’s many related points of interest, such as the Kittery Historical & Naval Museum. This seasonal treasure trove is located just over the state line off I95 and features an active historical database of Kittery—also available online for free. For a more rigorous dive into the town’s naval history, map out a tour of some of Kittery’s memorials and parks, such as Fort McClary, the Maine Sailors and Soldiers Memorial, and the USS Thresher Memorial. The fort, in particular, is a poignant example of military history preserved in dramatic fashion; one can almost feel the tension of bygone eras when soldiers scanned the open ocean beyond the mouth of the river, ever vigilant for threats.

Named for Kittery native Sir William Pepperrell—a decorated soldier and successful local merchant—Pepperrell Cove is a destination unto itself, and if the weather is accommodating, you should certainly set aside an afternoon to spend here, strolling, browsing, and noshing…because you’ll have options! The Bistro 1828 and the Ski Club offer full lunch and dinner menus along with panoramic views—dinner and a show!—and at Frisbee’s Wharf, you can pull your boat right on up, hop off, and soak in the sunshine while you wait for your seafood platter and beer. Or meander over to Provisions, where you can pick up all manner of essentials before finishing up your errand run with an ice cream cone from the walkup window at Mrs. & Me Ice Cream.

Another area worthy of a day trip, head to the Kittery Foreside area—just over the Memorial Bridge, to the east. Described by many as the “real Kittery,” this area is home to an up-and-coming area known as Wallingford Square, a veritable hotbed of eateries, shops, and other creative small businesses. Near the confluence of Government and Walker Streets, this area seems to hatch a successful new venture every week, all within walking distance of each other. Make a reservation at Black Birch and get an order of their crazy-good deviled eggs or poutine with a craft cocktail—or, for a no-reservation-required experience, stop into The Wallingford Dram or their sister restaurant, Anju Noodle Bar. And Loco Coco’s Tacos, just a few blocks to the northwest, offers fresh, authentic Mexican food and drinks in a casual, festive atmosphere (their mouthwatering burritos are enormous!).

Just outside the walkable area of Wallingford Square, you’ll find other casual eateries just waiting for you to discover them—like Warren’s Lobster House, just over the Memorial Bridge on the right. Their soup-and-salad bar alone is worth a visit (the cornbread is heavenly), and their comfort-seafood-laden menu has been satisfying New England palates for over 80 years. And just a few hundred yards away on Badger’s Island is Ore Nell’s Barbecue, a popular Texas-BBQ-style restaurant that is quickly earning accolades as one of the hottest new eateries in the state.

Heading “in-town,” you’ll come upon the Disneyworld of outlet shopping—approximately one mile of strip malls, restaurants, and specialty shops that will leave your head spinning. You’ll surely need a detailed plan of attack here—will you start at the world-renowned Kittery Trading Post (where you can get everything from a high-end fishing pole and kayak to a pound of Maine-made penuche fudge) and work your way through each of the outlet centers in turn (such as The Kittery Outlets, The Kittery Premium Outlets, and The Outlets at Kittery), each featuring its own host of brand-name offerings in clothing, home goods, gifts, and accessories? Or will you bypass them all and satisfy your appetite, first? Whether you hunger for a bite or a beverage, you won’t go wanting for options. Robert’s Maine Grill has a fabulous upscale menu (their crab and avocado melt is a taste sensation) right on the river—and for a more casual seafood dining outing, try Bob’s Clam Hut, across Route 1.

Outdoor activities are also on offer in Kittery—Seacoast Maritime Charters, located at Pepperrell Cove, features two beautiful vessels to choose from for any of their offered excursions, such as seal watches or a sunset cruise. Or, for a deep-sea fishing or scuba diving adventure, give Seafari Charters a call—where they’ll welcome you aboard with coffee, donuts, and a smile. Boats not your thing? Try Sea Point Beach, which is purported to have the “warmest water in Maine” (take this with a grain of sea salt, folks—it’s still Maine, after all), and is dog-friendly year-round (before 10 a.m. and after 5 p.m. during the summer). And for a less sedentary experience, Take Flight Adventures is a great option for a group—but be warned: This seasonal attraction isn’t for the fainthearted! Zipline tours and more than 65 rope-climbing activities will keep even the most enthusiastic and lion-hearted members of your entourage entertained.

Despite being the oldest incorporated town in Maine, Kittery is fast coming into its own—without over-gentrifying its true nature as a mariner community, dedicated to keeping true to its history while supporting residents, local business owners, and visitors alike.

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