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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Monson: The Town That Exported Darkness

Monson’s black slate ended up in the Eternal Flame at Arlington National Cemetery. That’s not a metaphor—that is real quarry stone from a little town in the Maine woods, cut, polished, and sent off to hold national grief in place. For a generation, this hill-town material became a presidential memorial and a staple of St. Patrick’s Cathedral, making Monson rich on the fact that America wanted permanence and was willing to pay for it. Then the quarries went quiet, and Monson turned into a lonely dot on Route 6—a place most people only notice when they are already late for somewhere else.

In this episode of Drive-Thru Towns, host Andrew Wilcox uncovers one of the strangest economic reboots in New England history. We explore how a town built on the brutal, wet-rock labor of Swedish and Finnish immigrants—who left behind a Nordic enclave of halls and churches in the North Woods—suddenly became a high-concept experiment in philanthropy.

In the 2010s, the Libra Foundation arrived with millions of dollars, buying up empty main street buildings and turning a fading quarry village into a curated arts colony. Today, Monson lives in a bizarre, beautiful contradiction: it is the last real civilization before Appalachian Trail hikers tackle the grueling 100-Mile Wilderness, creating a streetscape where exhausted, mud-caked backpackers share sidewalks with residency artists debating creative placemaking over lunch.

• The Aristocratic Stone: How Welsh immigrant William Griffith Jones accidentally discovered Monson’s legendary slate vein while riding a horse in 1870, changing the region's bloodstream forever.

• The Nordic Accent: Inside the influx of Scandinavian laborers who brought their language, businesses, and a practical relationship with winter to Piscataquis County.

• The Narrow Gauge Lifeline: The critical industrial role of the Monson Narrow Gauge Railroad, hauling heavy black stone from deep pits to global building markets.

• The Economy of "Cheap and Sufficient": How the post-WWII rise of cheap asphalt shingles and synthetic school blackboards retired Monson's business plan, leaving behind massive, dark tailing piles as industrial shadows.

• Revival by Purchase: Inside the million-dollar facelift that transformed a hollowed-out extraction town into a thriving, theatrical hub for sourdough habits and design degrees.

• The Edge of Endurance: Why serving as the official gateway to the 100-Mile Wilderness gives this resilient town a beautiful, utilitarian afterlife.

If you are drawn to the rugged places where old-world labor meets modern curation, follow the show on Spotify so you never miss an episode.

• Instagram: @50statefamily

• LinkedIn: Andrew Wilcox

• Email: wilcoxlegal@gmail.com

Swan Island: The Island Full of Furniture Where the Town Disappeared

The island is full of furniture, but the town is entirely gone. That is the unsettling reality of Perkins Township—better known today as Swan Island—a green smudge of land stranded in the middle of Maine's Kennebec River. Once a bustling, self-contained community of shipbuilders, ice harvesters, and farmers, it is now an uninhabited state wildlife area where deer and bald eagles outnumber people by a lopsided margin.

In this episode of Drive-Thru Towns, host Andrew Wilcox takes a short boat trip into a state of arrested decay. Swan Island has no bridge, no stores, and no modern residents, yet it holds five fully intact 18th-century homes still filled with domestic furniture and historic leftovers. It feels less like a demolished ruin and more like the 20th century simply got tired halfway through, packed a single bag, and wandered off downstream.

We trace the island's history from its deep roots as a summer camp for the Indigenous Abenaki people to its 19th-century industrial peak, when "cold was cargo" and winter was mined directly out of the river. We explore the slow, quiet subtraction that led the town to completely disincorporate in 1918 simply because there weren't enough people left willing to sit in the town office chairs, creating one of the most hauntingly preserved ghost towns in New England.

• Preservation by Neglect: What it feels like to walk through the historic Tubbs-Reed and Robinson houses, where the furniture stands waiting for owners who left eighty years ago.

• Mining the Winter: Inside the brutal, practical business of the Kennebec ice trade, where blocks of river ice were packed in sawdust and shipped as far away as India.

• The Slow Subtraction: How a toxic mix of upstream paper mill pollution, the invention of artificial refrigeration, and the shift from wooden ships to steel quietly choked out the island's economy.

• Death by Disincorporation: The quiet sting of 1918, when a functioning American town administratively vanished not because of a fire or a flood, but due to a total absence of volunteers.

• A Sentence with the Verbs Missing: Exploring the Steve Powell Wildlife Management Area, where a layout of roads, farms, and cemeteries has been entirely repurposed as an animal habitat.

If you are fascinated by the places where human history has been frozen in time and handed back to the wilderness, follow the show on Spotify.

• Instagram: @50statefamily

• LinkedIn: Andrew Wilcox

• Email: wilcoxlegal@gmail.com

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