Kittery: Bargains and Warships at the Gateway to Maine

Kittery is the oldest town in Maine, and somehow it still looks like it’s in a hurry. That is the joke hiding in plain sight at the state line. On one side of Route 1, you have the polite chaos of outlet traffic, sprawling parking lots, and vacationers hunting for discounted sweaters. On the other side—shielded behind high-security gates and layers of federal authority—sits a nuclear submarine repair facility that has been humming since the dawn of the republic. A town of bargains and warships, a tax base and a nuclear target, Kittery has spent nearly four centuries mastering the art of being two completely different places stitched together at the seams.

In this episode of Drive-Thru Towns, host Andrew Wilcox decodes the coastal compression algorithm of Kittery. We look past its famous public face as the "Gateway to Maine" to explore a town that learned long ago that geography can be weaponized, monetized, and touristified all at once.

We trace Kittery’s history from its 1647 incorporation and its role as a revolutionary shipbuilding powerhouse—boasting William Whipple, a local sea captain and the only Maine-born signer of the Declaration of Independence—to its massive transformation into a WWII military machine state. We untangle the permanent regional ribbing of a shipyard physically located in Maine but named after Portsmouth, New Hampshire, and look at how a town that once outfitted legendary warships successfully repriced itself to outfit tourists in fleece jackets and hiking boots.

• The First Engine: How the deep, rushing waters of the Piscataqua River allowed early English settlers to turn timber and raw labor into an international maritime machine.

• The Shipyard State: Inside the Portsmouth Naval Shipyard on Seavey Island—the oldest continuously operating Navy yard in the country—which launched an astonishing four submarines in a single day in January 1944.

• The Wartime Machine State: When Kittery's population exploded during WWII, bending every local boarding house, diner, and family schedule around the urgent 24/7 clock of naval defense.

• The Castle on the River: The haunting presence of the abandoned Portsmouth Naval Prison, a monolithic military relic that still dominates the local waterfront landscape.

• The Outlet Pivot: How a post-industrial town facing Cold War defense cuts successfully rebranded Route 1 into the "Outlet Capital of the World," anchored by the legendary, homegrown Kittery Trading Post.

• The American Pattern: A broader look at how historic American towns don't just age—they reprice themselves, transitioning seamlessly from launching empires to selling weekend socks.

If you want to explore the fascinating, high-stakes dual identities of America's great border towns, follow the show on Spotify.

• Instagram: @50statefamily

• LinkedIn: Andrew Wilcox

• Email: wilcoxlegal@gmail.com

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