Things to Do in Kittery, Maine [A Local’s Guide]

7.3.2023

C’mon up to Kittery.

Known far and wide as an outlet shopper’s paradise, this Maine town by the sea (incorporated in 1647) charms visitors with its secluded beaches, historic military forts and a tantalizing lineup of memorable spots for fun and/or fine dining.

Of course, the world-famous Kittery Outlets district on Route One is a bustling bargain shopping zone for deep discounts on big-name brands. But visitors to Kittery will also want to explore the town’s oceanfront vistas, as well as one of the coolest little downtown districts in all of New England — Kittery Foreside.

Kittery’s close proximity to Portsmouth, located just across the river in New Hampshire, gives visitors and locals alike easy access to even more local attractions, historic sites, arts and culture, and dining options

Shopping in Kittery, Maine

Attention shoppers: With over 120 popular brand name outlet stores, Kittery’s Route One shopping district is known far and wide as a hotspot for retail bargains and is cleverly touted as “America’s Maine Street for Shopping.”

The Kittery Outlets encourage you to: “Think of us as New England’s Fashion District — featuring the latest and greatest in women’s and men’s apparel, children’s wear, active wear, lingerie, sporting goods, shoes, fashion accessories, home furnishings, housewares and specialty items.” A quick sampling of the big-name brands represented here includes: Lululemon, UnderArmour, Crate and Barrel, Eddie Bauer, Ralph Lauren, The Kitchen Outlet and countless more.

The importance of local history to the identity of both Kittery and nearby Portsmouth (est. 1623) is also seen in the region’s retail community. One great example of this is the Kittery Trading Post — a crown jewel of the Kittery shopping experience.

Acquired by Bing Adams in 1938 as a modest one-room trading post and gas station, it has seemingly been expanding ever since. Here at Weathervane Seafood Restaurants, we’ve been next-door neighbors of the Trading Post since 1969, and have watched it evolve into a destination experience that offers “three levels of the most extensive selection of outdoor recreational equipment, clothing and footwear in New England.”

Sightseeing in Kittery, Maine

Not far from the shopping district, the Kittery seascape is dotted with scenic vistas, beaches, lighthouses and historic forts.

With Fort McClary, Fort Foster, a naval history museum and the busy, two-century-old Portsmouth Naval Shipyard, the town’s role in America’s national defense is proudly and prominently on display.

Fort Foster Park — Locals love Fort Foster for its beach access, but the park is also home to old military fortifications. Located on the southwest tip of Gerrish Island, it is the site of a historic fort that was active from around 1900 through the late 1940s. In addition to several surviving fort structures, it has three small but sandy beaches, a trail system, restrooms, picnic areas and scenic views of the entrance to Portsmouth Harbor, Whaleback Light, Portsmouth Harbor Light and Fort Constitution.

Fort McClary — Strolling around the grounds of Fort McClary, an important U.S. military defensive position since 1689, it is easy to imagine soldiers using the cannons and thick-walled fortresses to defend Portsmouth Harbor. In fact, the fort periodically hosts costumed Civil War reenactments. Named for NH native Major Andrew McClary, killed in the 1775 Battle of Bunker Hill, the fort was established in 1808. The state of Maine says the site was manned during five wars — Revolutionary War, War of 1812, Civil War, Spanish-American War and World War I — but, “like most other Maine forts, it saw little conflict.” Today, it is a popular picnic spot featuring historic nooks and crannies to explore and dramatic views of the harbor, its lighthouses and the Wood Island Life Saving Station.

Portsmouth Naval Shipyard – Established in 1800, the shipyard is not a tourist attraction, but it is a dominant piece of Kittery’s visual environment, an important employer and economic engine, and a crucial piece of local history. Taking a river and harbor cruise is a fun way to learn more about the shipyard, including the ominous, castle-like former naval prison that looms over the harbor. The shipyard turned out its first military vessel, the 74-gun USS Washington, in 1814. Today, its central mission is the repair and modernization of the U.S. Navy’s nuclear-powered attack submarine fleet

Kittery’s naval shipbuilding heritage is also on display at the nearby Kittery Historical & Naval Museum and across the river in Portsmouth where the USS Albacore, built and commissioned at the Portsmouth Naval Shipyard in 1953, is now a submarine museum that is open to visitors.

A walk or drive across the Memorial Bridge into neighboring Portsmouth connects visitors to a great many more historic attractions, including the city’s famed living history museum, Strawbery Banke.

Arts and Culture in Kittery, Maine

Local arts venues in Kittery include The Dance Hall, which hosts an eclectic mix of artists in a historic 1928 Grange Hall. The nearby Star Theatre at the Kittery Community Center is billed as “a unique venue for live theatre, performance events, lectures, trainings, workshops and movies,” and more.

A vibrant arts and culture scene just across the river is also part of the attraction for visitors to Kittery. Notable arts venues in Portsmouth include The Music Hall (established in 1878), the Seacoast Repertory Theatre, 3S Artspace, The Players’ Ring, Jimmy’s Jazz & Blues Club and the Museum of New Art | Portsmouth.

Eating and Drinking in Kittery, Maine

When in Kittery, you’ll definitely want to check out Kittery Foreside — the funky, happening downtown business district.

The revitalized Foreside District, also called Wallingford Square, gets rave reviews from the foodies at The Food Lens, who rank Foreside “at the forefront of good food, craft beer and cocktails

Of course, our favorite eatery will always be the fun, family seafood restaurant opened by our founders, Ray and Bea Gagner, back in 1969 and operated today by their grandson Jeremy. So, if you ever have a craving for fresh-caught lobster and other savory treats from the sea — always served with a smile — we hope you’ll stop by and visit us at Weathervane Seafood Restaurants.