Doug Cress of Enterprise Realty   Email: doug@cress.co (dot co)   Call/Text: 212-203-5251

Enterprise Realty Office: 203-929-6311

Doug Cress of Enterprise Realty
Email: doug@cress.co (dot co)  Call/Text: 212-203-5251
Enterprise Realty Office: 203-929-6311

Where the Housatonic River spills into Long Island Sound, the waters get tricky—riptides, sandbars, and shifting currents that don’t care how experienced you are behind the helm. For more than two centuries, the Stratford Point Lighthouse has marked the edge of that chaos, steady and stubborn against time, tide, and the occasional hurricane.

But Stratford Point is more than a beacon—it’s a living memory, anchored by the lighthouse, the keeper’s house, and the people who gave this lonely post its heart.

From Bonfire to Beacon

Before the lighthouse, locals lit bonfires when ships were expected on foggy nights. That evolved into fire baskets hoisted on poles. In 1821, Congress allocated $4,000 to formalize the effort, and by 1822, Stratford Point Lighthouse was operational—a 28-foot octagonal wooden tower painted in alternating black and white stripes, attached to a keeper’s cottage.

The first keeper, Samuel Buddington, made a mess of things—literally. An 1837 inspection reported oil dripping through the lantern and a general state of neglect. After his death in 1848, his wife Amy took over and quickly brought order. Her son Rufus followed, holding the post through personal tragedy when four of his eight children died during the diphtheria outbreak of 1861–62.

A Kid, a Lamp, and a Steady Hand

In 1871, Keeper Benedict Lillingston and his son left the lighthouse to help a vessel in distress. That night, twelve-year-old Lottie Lillingston—left alone—noticed the light had gone out. Having watched her grandfather work, she lit a brass safety lamp, climbed the tower, and got the rotation system running. That small, steady glow helped guide the steamer Elm City safely past the point.

Storms, Bell-Tolling Marathons, and Mermaids

In 1881, the original structures were replaced with the cast-iron tower and two-story, eight-room keeper’s house still standing today. That house—restored and maintained through a town-Coast Guard partnership—is now occasionally open to the public.

One of the most memorable keepers was Theodore “Theed” Judson, who served from 1880 to 1919. He once claimed to have seen a dozen mermaids offshore and said he salvaged one’s oyster-shell hairbrush. His daughter Agnes gained local fame at 17 after diving into rough waters to rescue two fishermen, hauling them to shore with the help of her brother.

The lighthouse endured countless storms. During one, the fog bell tolled for 104 hours straight, took a break, then rang another 103. The family took shifts winding the clockwork mechanism.

The Final Keepers

Three long-serving civilian keepers marked the end of manual operations:

  • Theed Judson (1880–1919)
  • William Petzolt (1919–1946)
  • Daniel McCoart (1946–1963), a Navy veteran and former boxer who lived at the lighthouse with his family and maintained it to high standards, earning multiple federal inspection awards.

Headless Years and Restoration

In 1969, the tower lost its lantern to make room for automated aerobeacons. The original lantern was displayed at Boothe Memorial Park until 1990, when it was restored and returned to the top of the tower.

Automation officially began in 1970, but Coast Guard crews remained on-site until 1978. In the decades since, the town has helped preserve and reactivate the site for public tours. Restoration continued into 2023, including paint and environmental remediation.

The Flying Santa

Beginning in 1929, lighthouse keepers like those at Stratford Point received a special visitor each Christmas: The Flying Santa. Aviation pioneer William Wincapaw started the tradition, flying over remote stations to drop holiday care packages filled with coffee, candy, newspapers, and gifts—small tokens of appreciation for the men and women who kept the lights burning through isolation and storms. The tradition endured for decades and included Stratford Point in its route, bringing a moment of cheer to families stationed at the edge of land and sea.

Still Lighting the Way

Stratford Point Lighthouse may be automated, but its legacy is very human. From bonfires and brass lamps to heroics and hurricanes—and even Santa Claus in a floatplane—it’s a place where history, myth, and maritime life converge. The light still shines, quietly doing its job, just as it has for more than 200 years.

Cress is an innovative real estate advisory firm representing buyers and sellers of high-end properties throughout Fairfield County, CT and beyond. On the sell side, Cress delivers marketing-driven support designed to expand visibility and maximize outcomes. Through its co-listing model, Cress partners alongside listing agents to provide digital-first distribution, high-quality content creation, and proactive demand generation strategies that extend well beyond traditional MLS exposure.

On the buy side, Cress offers flat-fee representation and commission rebate programs that bring efficiency and transparency to luxury transactions while maintaining a high standard of service. Known for strategic insight, modern marketing execution, and deep local knowledge, Cress provides a smarter, more aligned approach to buying and selling real estate.

For more information, visit www.callcress.com.

Doug Cress
(212) 203-5251
doug@cress.co
License #RES.0832278
Fairfield County, CT

Enterprise Realty Inc.
License #REB.0751297
45 Huntington Plaza
Shelton, CT 06484