Great Captain Island
Dream of tracing the Long Island and Connecticut coastlines? Sail into history with us instead of just seeing it.
Monty’s Ark Adventures invites you aboard a private charter for the ultimate Long Island Sound Lighthouse Tour.
This isn’t a crowded ferry trip. It’s a customized journey to witness 14 historic beacons—the “Castles of the Sound”—up close. We’ll explore their stories-heroic rescues, tragic shipwrecks and eerie legends still echoing in the 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 western end of Long Island Sound holds dramatic, historic lights marking rocky shoals near the New York–Connecticut line
1. Execution Rocks Lighthouse
Coordinates: 40° 52′ 41.3” N 73° 44′ 16.3” W
History & Purpose: Built around 1850, this granite tower warned ships from a deadly reef near New Rochelle and Sands Point. It remains an active aid to navigation.
Legend and Lore: This lighthouse carries one of the darkest names and legends in maritime history. Folklore says the British chained prisoners and enslaved people to rocks, leaving them to drown as tides rose. This macabre practice is said to be the origin of the name. In the 1920s, serial killer Carl Panzram admitted to dumping bodies near the light, sealing its haunted reputation.
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: A Native American legend says the Siwanoy chased the devil Habboamoko out of the region, giving the reef its name. The devil leapt across submerged rocks toward Long Island, hurling boulders at his pursuers as he fled.
3. Sands Point Lighthouse
Coordinates: Not an active aid to navigation.
History & Purpose: Built in 1809, this brownstone tower guided ships until 1922, when Execution Rocks Light took over navigation duties.
Legend and Lore: Though not haunted, its spot near Long Island’s Gold Coast—the setting of The Great Gatsby—adds a touch of literary charm.
4. Great Captain Island Lighthouse
Coordinates: 40° 58′ 54” N 73° 37′ 24” W
History & Purpose: Builders completed the granite structure in 1868. It replaced 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. Preservationists later restored the historic tower.
Legend and Lore: Some say the island honors Captain Daniel Patrick. Others claim Pirate Captain Kidd buried treasure along its 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: Built in 1890, the original wooden tower sat on a caisson to mark the entrance to Cold Spring Harbor. Decommissioned in 1965, and a skeletal tower now serves as the active aid. A local family purchased the lighthouse for $1 and move it 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: Built from 1910–1912, this Beaux-Arts lighthouse replaced Lloyd Harbor Light and still resembles a miniature castle. In 1984, locals rallied to save the lighthouse—an inspiring story of teamwork and community pride.
Lifesaving Activities: The lighthouse served to ensure safe entry into the busy harbor. It helped prevent 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 served a crucial purpose for navigating the dangerous rocks and reefs extending from the point.
Shipwrecks & Heroism: Eaton’s Neck has seen many shipwrecks—over sixty in an 1811 storm. Most famously, the steamship Lexington caught fire and sank nearby in 1840. That event became one of the worst early steamship tragedies in American history. In 1850, Keeper Benjamin Downing earned praise for rescuing a sailor 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 serving as an instrumental aid 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: Its isolation—five miles from shore—drove keepers to despair. In 1905, Assistant Keeper Julius Koster went mad and attacked a colleague. 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 schooner Florence E. Turner also wrecked nearby in 1873.
11. Penfield Reef Light
Coordinates: 41° 07′ 01” N 73° 13′ 19” W
History & Purpose: Built in 1874 off Fairfield, Connecticut, stone masons constructed one of the last major offshore masonry lights 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. Locals say Jordan’s ghost still helps sailors in distress—a tragic figure turned eternal watchman.
12. Peck Ledge Light
Coordinates: 41° 04′ 38.4” N 73° 22′ 11.38” W
History & Purpose: A classic cast-iron “sparkplug” lighthouse constructed in 1906 to mark a hazardous ledge and improve navigation into Norwalk Harbor.
Keeper Lore: The keepers were colorful characters—one stole lobsters; another started a fire while fixing traps, then saved the light himself. 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: Authorities established this Victorian-style light in 1827 and later, in 1868, replaced it with the current structure. 1902 brought the decommissioning when Greens Ledge Light became operational.
Legend and Lore: The light is rumored to be haunted by the ghost of Captain Robert Sheffield. After decommissioning, rumrunners used the island to smuggle liquor. Nearby, the 1840 Lexington disaster marked a tragic chapter 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: Some say a pirate named Green was chained to the reef as a warning. Others think this light inspired the “green light” in 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 an experience big tours can’t. Spend more time at your favorite lighthouses, take amazing photos, and dive into history. Immerse yourself in the dramatic history of the Long Island Sound Lighthouse Tour.
Whether you love history, hauntings, or just great views, our private charter is your ticket to adventure.
To learn more about historic lighthouses visit https://www.lighthousefriends.com/
Contact Monty’s Ark Adventures
📍 Website: montysarkadventures.com
📞 Call us at: 516-636-3094
Chart Your Adventure. Live the Legend. Reserve Your Charter.