Tomorrow is New Haven’s 388th birthday.
But the three winners of our birthday riddles contest, this time highlighting New Haven’s role in the birth of America, will each have something more to celebrate: a $50 gift certificate to a restaurant of their choice. They’ll also receive two current copies of The Chaser, our food and drink passport filled with complimentary offers from some of New Haven’s favorite restaurants and bars.
We’ll announce the winners as soon as they’ve been notified and accepted their prizes. Meantime, let’s unwrap some riddles.
The solution to the first, “With steady pen, he signed all four—the only one, if keeping score,” is New Haven’s greatest statesman, Roger Sherman. The only person to sign America’s four major founding documents, he patiently nurtured nationhood through the Articles of Association in 1774, which formalized a boycott of trade with England; the Declaration of Independence in 1776; the Articles of Confederation in 1777; and, in 1787, the Constitution, whose adoption hinged on the Connecticut Compromise proposed by none other than Roger Sherman. At the same time, Sherman was also serving as mayor of New Haven, a title he would keep even after joining Connecticut’s first federal congressional delegation in 1789.
The answer to the second riddle, “Still holding torch for olden times, this place was torched in ’79,” is the Pardee-Morris House. The home was burned in 1779 during the British raid of New Haven, then rebuilt using some of the original bones. Today the property is preserved as a historic site by the New Haven Museum, which periodically opens up the grounds for summertime concerts, workshops and hangouts.
Riddle #3, “With life to give for liberty, this spy was brave but too naive,” describes the city/state/national folk hero Nathan Hale. Graduating from Yale at age 18, Hale worked as a schoolteacher before enlisting, eventually receiving what was supposed to be a teeth-cutting counterintelligence assignment in patriot-held New York. But the city fell to the British just days after Hale’s arrival, and, despite being surrounded by enemies in an unfamiliar place with no real training, Hale decided to forge ahead anyway, working to cultivate what he hoped would be unsuspecting British intel sources. Instead, a group of British loyalists almost immediately clocked him, getting him to spill his own secrets simply by pretending to be patriots. Soon hanged by the redcoats and mourned by the rebels, Hale became inextricably linked with a set of famous and likely apocryphal last words echoed in the riddle: “I only regret that I have but one life to give for my country.”
Riddle #4, “His paintings shaped the founding scenes—and founded their home for ~centuries,” nods to John Trumbull, an artist whose epic Revolutionary War compositions exalt key moments and mold America’s perception of its origins to this day. In 1832, he sold those paintings to Yale on the condition that the college would devote a space to their permanent display—an act that birthed the Yale University Art Gallery, where they remain on view nearly two centuries later.
The fifth riddle, “In first of turns, he held the key, to Saratoga’s victory,” describes one of the rebellion’s greatest patriots, before he wasn’t: New Havener Benedict Arnold. During the second Battle of Saratoga—the turning point of the war, when Arnold was not yet a turncoat, which is why the riddle calls it his “first of turns”—Arnold defied the much more cautious approach of his superior officer, General Horatio Gates, instead leading charge after charge against redcoat entrenchments, which he and his rallied men felled like dominoes. At the cost of a devastating leg injury during the final attack, Arnold’s relentless ferocity and the victory it produced put fear into the hearts of America’s enemies and courage into the hearts of America’s friends—including the French, who were convinced by the battle’s outcome to enter the war on America’s side.
A far less controversial but equally less remembered figure satisfies riddle #6, “A square with park still bears his name, unbloomed in nation’s halls of fame”: New Havener David Wooster. Namesake of Wooster Square and its (locally) famously flowering park, General Wooster was a military man through and through, having joined his first war in 1739 the year after he graduated from Yale. His time in the Revolutionary War was cut short, however, in 1777, when he took a mortal bullet while chasing British raiders out of southwestern Connecticut. Amazingly, he did that at 67 years old, an age when few would choose to battle at the front, let alone as a general who could easily have rationalized hanging back.
Finally, because I didn’t bake in enough disambiguation, we’re accepting two answers for the seventh riddle, “Made to fend off enemies, its duties now guard memories.” The first solution, part of a successively expanded installation called Fort Nathan Hale, is Black Rock Fort, a commemorative harborside cannon deck evoking the one local militiamen used against the invading British force that burned the Pardee-Morris House. The second accepted solution is the town militia itself: the Second Company of the Governor’s Foot Guard, formed in 1775 under the shadow of a looming war and persisting today as a mostly ceremonial outfit.
Not that there’s anything wrong with that. Ceremony, after all, is what birthdays are about.
Written by Dan Mims. Image 1, featuring three of John Trumbull’s Revolutionary War paintings at the Yale University Art Gallery, photographed by Dan Mims. Image 2, featuring the Pardee-Morris House, photographed by Cara McDonough. Image 3, featuring members of the Second Company of the Governor’s Foot Guard during a Powder House Day celebration in 2023, photographed by Dan Mims.
