The Oldest Town In Maine Is A Serene Coastal Gem Full Of Historic Sights, Shops, & Seafood

Poised on the Piscataqua River, just across the Memorial Bridge from Portsmouth, New Hampshire, is the old shipbuilding town of Kittery, Maine. Settled in 1623, it is widely regarded as the oldest town in the state. Kittery is an effortless side trip for anyone visiting Portsmouth, and is easy to get to, whether you're flying into Boston Logan International Airport (about 56 miles away) or Portland International Jetport (only a 48-mile drive). This waterfront village would absolutely make a cute and serene addition to your next breathtaking New England road trip.

Once you've crossed into Maine, the downtown area, also known as Kittery Foreside, quickly unfolds — a stylish blend of trendy cafés, boutiques, and chef-driven eateries. Before you do anything, stop at Lil's Cafe. Get yourself a cappuccino sweetened with real maple syrup and pair that with one of the cafe's famed crullers, round fried pastries that seem to just disintegrate in your mouth. Afterwards, wander Wallingford Square, where artisan galleries and locally owned boutiques await you. Then head to the Maine Visitor Information Center in Kittery — your friendly travel hub for maps, brochures, parking, restrooms, and local tips.

This town wears its history with pride. In Kittery Point, drive or stroll past architectural treasures like the Georgian-style Lady Pepperrell House (built in 1760) — a National Historic Landmark open to the public only several times a year — and the rare Greek Revival Robert and Louisa Traip House, from about 1839. Over at Kittery Foreside, the Romanesque-Revival Rice Public Library, built in 1889 and beautifully restored in 2022, offers cultural character and a story of civic generosity.

For a peaceful outdoor interlude, head to Fort Foster Park, on the tip of Gerrish Island. It's a former coastal defense fort turned into a walkable, scenic park, with beaches, hiking trails, and tidal-pool studying opportunities. Another waterfront gem, Fort McClary State Historic Site, presents a storied blockhouse and sweeping views from Revolutionary-era ramparts — a must-see for history enthusiasts.

For a maritime tale, don't miss a boat tour to the Wood Island Life Saving Station. Built in 1908, it was recently restored, and is accessible by reservation June through September. Tours include a boat ride from Pepperrell Cove, guided access to the watchtower, boathouse, and rotating exhibits for a fascinating peek into rugged coastal rescue history. If this taste has you looking for another slice of island life off Maine's coast, consider adding a day trip to the charming Casco Bay, on the other side of Portland, to get the whole Maine waterfront experience.

Kittery's retail reputation is legendary. The region's "Golden Mile" of shopping along Route 1 includes Kittery Premium Outlets — over 120 brand-name stores — and the Kittery Trading Post, a local institution open since 1938, offering outdoor gear and regional flair. After shopping, treat yourself to iconic Maine seafood. Robert's Maine Grill offers fresh lobster rolls, oysters, and riverside views — calm, modern, and delicious. Not far away, Tributary Brewing Company serves up craft beers in a laid-back, dog-friendly taproom. For a quieter slice of nature, explore the nearby Rachel Carson National Wildlife Refuge, about 20 minutes away in Wells. A well-marked, accessible one-mile loop trail through salt marshes makes it a peaceful bird-watcher's paradise — ideal for reflection with binoculars and mosquito repellent in tow. 

Perhaps after a full day of outlet shopping, hiking, and lobster roll-devouring, grab one last cruller from Lil's and go sit in the pretty John Paul Jones Park. Feel the breeze on your face, listen to the cheery chirping of birds, and read a little if you brought a book. Then head back to Memorial Bridge, taking in the fishing boats, the gleaming Piscataqua, and fenced-in chickens you encounter along the way. Back in Portsmouth, you'll find boutique hotels while York, Maine, and York Harbor offer motels and inns. Expect to pay about $150 to $250 a night on summer weekends. However you stay, Kittery would make a great introduction to the Maine coast. Maybe even continue north, through Portland, then the underrated town of Boothbay Harbor, all the way to Eastport to really experience the coast.