Charting History: The Ultimate Long Island Sound Lighthouse Tour on a Private Boat Charter

Have you ever dreamed of tracing the coastlines of Long Island and Connecticut, not just seeing history, but sailing right into it Monty's Ark Adventures invites you aboard our exclusive private boat charter for the most comprehensive and unforgettable Long Island Sound Lighthouse Tour.

This isn't a crowded ferry trip; this is a customized journey to witness 14 historic beacons—the "Castles of the Sound"—up close. We'll delve into their compelling histories, the tragic shipwrecks they averted, and the strange legends that cling to their granite walls.

Join us as we navigate the nautical chart, introducing the lighthouses you will see on this epic voyage.

The Haunting Harbors of the Western Sound (NY/CT)

The narrow, high-traffic western end of Long Island Sound is home to some of the most dramatic and storied lights, many of which mark dangerous, rocky shoals near the New York and Connecticut borders.

1. Execution Rocks Lighthouse

• Coordinates: 40° 52' 41.3'' N 73° 44' 16.3'' W
• History & Purpose: Completed around 1850, this formidable granite tower was built to warn ships away from a treacherous reef near the boundary of New Rochelle and Sands Point, New York. It remains an active aid to navigation.
• Legend and Lore: This lighthouse carries one of the darkest names and legends in maritime history. Folklore claims that during the colonial era, the British would execute prisoners—and in some accounts, enslaved people—by chaining them to the rocks at low tide, leaving them to drown as the water rose. This macabre practice is said to be the origin of the name. Adding to the chilling lore, the infamous serial killer Carl Panzram later confessed in the 1920s to dumping the bodies of several victims near the light, cementing its reputation as one of the most haunted lighthouses in the U.S.

2. Stepping Stones Lighthouse

• Coordinates: 40° 49' 27.6'' N 73° 46' 29.1'' W
• History & Purpose: Constructed in 1877, this Victorian-style, square red brick lighthouse marks a dangerous, extensive reef near the New York entrance to the Sound.
• Legend and Lore: The reef gets its name from an old Native American legend. The tale states that the Siwanoy people were chasing Habboamoko, a mischievous devil figure, out of the region. The devil used the large, submerged rocks as "stepping stones" to escape across the Sound to Long Island, flinging boulders back at his pursuers as he fled.

3. Sands Point Lighthouse

• Coordinates: Not an active aid to navigation.
• History & Purpose: Established in 1809, this early octagonal brownstone tower on the Great Neck Peninsula was eventually deactivated in 1922 when the Execution Rocks Light assumed its role as the primary navigational aid for the area.
• Legend and Lore: While no intense ghost stories are directly tied to this light, its historic location near the grand estates of Long Island’s Gold Coast—the real-life setting for F. Scott Fitzgerald's The Great Gatsby—lends it a unique historical prestige and connection to American literature.

4. Great Captain Island Lighthouse

• Coordinates: 40° 58' 54'' N 73° 37' 24'' W
• History & Purpose: The current granite structure was completed in 1868 (replacing an earlier 1829 tower) on an island off Greenwich, Connecticut. It served as a vital guide until 1970, when it was replaced by a skeletal tower, but the historic tower was later restored.
• Legend and Lore: The island’s name is subject to two pieces of lore: first, that it was named for Captain Daniel Patrick, an early Greenwich military figure; and second, the more romantic legend that Pirate Captain Kidd buried a vast treasure of gold and silver somewhere near the island's tide line.

5. Stamford Ledge Light

• Coordinates: 41° 00' 48'' N 73° 32' 31'' W
• History & Purpose: Built in 1882, this offshore light sits on a submerged ledge to guide vessels into Stamford Harbor, preventing groundings on the surrounding reefs.
• Legend and Lore: This light is rumored to be haunted by the ghost of a tragic keeper named "Ernie" Randolph. The story claims that in the 1930s, Ernie’s wife ran off with the captain of a Block Island ferry that routinely passed the station. Distraught, Ernie took his own life. Subsequent keepers reported strange phenomena, including the light being mysteriously turned on and off, and heavy doors opening and closing.

The Storied Central Sound (Long Island's North Shore)

Moving east along the New York coast, we encounter lights marking the entrances to the great harbors of Long Island, each with compelling stories of dedicated service and dramatic rescues.

6. Cold Spring Harbor Lighthouse

• Coordinates: 40° 54' 51.0'' N 73° 29' 35.2'' W
• History & Purpose: The original 1890 wooden tower was built on a caisson to mark the entrance to Cold Spring Harbor. The original structure was decommissioned in 1965, and a skeletal tower now serves as the active aid. The original wooden tower was famously purchased for $1 and moved to the mainland.
• Legend and Lore: This light is associated with a charming, peaceful piece of lore. One local memory recounts a light keeper who kept a piano at the isolated station. On quiet nights, his music would drift across the water, offering a moment of unexpected beauty and solace to passing mariners.

7. Huntington Harbor Lighthouse

• Coordinates: 40° 54' 38.6'' N 73° 25' 52.7'' W
• History & Purpose: Constructed between 1910 and 1912, this unique structure in the Beaux-Arts style resembles a small castle and replaced the older Lloyd Harbor Light. Facing planned demolition in 1984, the light was saved by a massive grassroots effort from the Huntington Lighthouse Preservation Society, making its story one of community resilience.
• Lifesaving Activities: Its primary role was to ensure safe entry into the busy harbor, preventing the type of minor to major accidents that plagued the area before its construction.

8. Eatons Neck Lighthouse

• Coordinates: 40° 15'' N 73° 23' 48'' W
• History & Purpose: First lit in 1799, this is the second oldest lighthouse on Long Island and remains an active Coast Guard station today. The light was crucial for navigating the dangerous rocks and reefs extending from the point.
• Shipwrecks & Heroism: The Eatons Neck area has been a site of significant maritime disasters, including a storm in 1811 that claimed over sixty ships. Most famously, the steamship Lexington caught fire and sank nearby in 1840, an event that became one of the worst early steamship tragedies in American history. Keeper Benjamin Downing was recognized for his heroism in 1850 when he rescued a mariner clinging to an overturned schooner.

9. Old Field Point Lighthouse

• Coordinates: 40° 58' 37.2'' N 73° 07' 06.9'' W
• History & Purpose: Built in 1869 (replacing an 1823 tower), this elegant light marked the western edge of the formidable Stratford Shoal. It was instrumental in helping ships avoid the dangers of the central Sound.
• Keeper Lore: The station is celebrated for the history of its keepers, notably Elizabeth Smith and her daughter, Mary Foster, who successively served as head keepers for many years, showcasing a multi-generational commitment to maritime service.

The Offshore Castles and Reefs (Central/Eastern CT)

This leg of the journey takes us to the isolated, water-bound lights that stand as sentinels on remote shoals and ledges in the heart of Long Island Sound.

10. Stratford Shoal Middle Ground Lighthouse

• Coordinates: 41° 03' 35'' N 73° 06' 05'' W
• History & Purpose: Completed in 1878, this massive granite and masonry structure sits on a man-made island on the exposed Stratford Shoal. It is rightly known as one of the "Castles of the Sound."
• Legend and Lore: Due to its extreme isolation—over five miles from any shore—it bred loneliness and despair among its keepers. The most disturbing incident involves Assistant Keeper Julius Koster in 1905, who went insane, attacked a colleague, and attempted to destroy the lens. Koster is said to have later taken his own life and is believed to haunt the lighthouse, with his spirit still throwing objects and slamming doors. The light was also near where the schooner Florence E. Turner was wrecked in 1873.

11. Penfield Reef Light

• Coordinates: 41° 07' 01'' N 73° 13' 19'' W
• History & Purpose: Built in 1874 off Fairfield, Connecticut, this was one of the last major offshore masonry lights constructed in the U.S., built in the Second Empire style.
• Shipwrecks & Haunting: The light's history is shadowed by the tragic death of Keeper Frederick Jordan, who drowned on December 22, 1916, while attempting to row ashore for Christmas. His ghost is the subject of local legend; his replacement reported seeing Jordan's specter and finding the logbook mysteriously opened to the page detailing his death. Stories persist that Jordan's ghost has appeared to help mariners in distress, transforming a tragedy into a tale of an eternal, selfless watchman.

12. Peck Ledge Light

• Coordinates: 41° 04' 38.4'' N 73° 22' 11.38'' W
• History & Purpose: A classic cast-iron "sparkplug" lighthouse, it was constructed in 1906 to mark a hazardous ledge and improve navigation into Norwalk Harbor.
• Keeper Lore: Its history is marked by the wild antics of its keepers, including the time a keeper was arrested for stealing lobsters, and another time when a keeper saved the light from a serious fire he had accidentally started himself while repairing lobster traps. The light also saw the grounding of the steamship Middletown in 1913, which required a significant rescue effort.

13. Sheffield Island Light

• Coordinates: 41° 04.881' N 73° 25.15' W
• History & Purpose: This Victorian-style light was established in 1827 and replaced by the current 1868 structure. It was decommissioned in 1902 when Greens Ledge Light became operational.
• Legend and Lore: The light is rumored to be haunted by the ghost of Captain Robert Sheffield. After its decommissioning, the isolated island was used by rumrunners to smuggle alcohol during Prohibition. The area also holds the somber distinction of being near the site of the Steamboat Lexington fire and sinking in 1840, one of the worst maritime tragedies in the Sound's history.

14. Greens Ledge Light

• Coordinates: 41° 02' 30'' N 73° 26' 38'' W
• History & Purpose: Completed in 1902, this sparkplug light on a concrete caisson took over duty from Sheffield Island Light. Its construction on a difficult reef was a major engineering feat of the era.
• Legend and Lore: Legend holds that the ledge is named after a pirate named Green who was executed and chained to the reef as a warning to other buccaneers. Because of its location and its striking light, some literary historians believe Greens Ledge Light may have been the inspiration for the famous, symbolic "green light" featured across the bay from Jay Gatsby’s mansion in the novel The Great Gatsby.

Book Your Private Journey to the Castles of the Sound

Seeing one of these historic lights is a wonderful experience; seeing all fourteen—from the sinister Execution Rocks to the heroic Eatons Neck—on a seamless, private charter is an adventure unlike any other.

Monty's Ark Adventures offers the intimacy and flexibility that large tours cannot match. Our private boat charter allows you to spend more time near the lighthouses that pique your interest, take stunning photographs, and truly immerse yourself in the dramatic history of the Long Island Sound Lighthouse Tour.

Whether you are a maritime historian, a paranormal investigator, or simply seeking a spectacular day on the water, our private boat charter is the perfect vessel for charting history.

Contact Monty's Ark Adventures today to book your custom Long Island Sound Lighthouse Tour.

Visit our website: montysarkadventures.com or call us at: 516-636-3094

Chart Your Adventure. Live the Legend. Reserve Your Charter.