A drawing of the Stewart family‘s former estate by Thomas Royal Waite in 1887, as reproduced in the April 14, 1912, edition of the New Haven Register.

Rocky Road

Little do most people know of the eccentric characters who once roamed the wooded paths and craggy cliff walks of our beloved East Rock Park. These irregular recluses on the ridge range from the broke heartbroken hermit Elisha Turner, who died alone in 1823, to Newell Hall and Elizur Hubbell, who built a stone resort (pictured above) and bowling alley at the summit in 1840. After that venture failed, an English couple, Mr. Charles Smith and his wife, moved there in 1850. But their stay was cut short that fall when they were murdered by their would-be robber James McCaffrey. The strange stone house was then abandoned and said to be haunted, but it was later opened as a hostel that attracted even stranger strangers to the place.

The oddest of them all was its proprietor: Milton J. Stewart. Stewart began his stay in 1853 by squatting atop the summit. The 30-year-old was a stone dealer from New Hampshire, and, whether by eventual purchase or adverse possession (available historical records are inconclusive on this point), he boldly claimed ownership of the whole rock. He resided there with his wife, Ann, and their son, also named Milton J., who was born on the rock in May of 1865. Over the years, the elder Milton added rambling stone additions to the old house and eventually opened it up as a small hotel with rooms for a few guests.

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When the city began planning to make East Rock one of its new public parks in 1880, Milton protested. He closed all access roads and warned visitors from attempting to step foot on his property, with rumors surfacing that Milton was brandishing a gun to fend off trespassers. On one occasion on May 15, 1882, he chased off two amblers who were enjoying the serenity of the woods, in the process striking one of them in the head with his fist, resulting in a night in jail for him.

Trouble continued with a vicious incident on June 26, 1882. Milton’s wife, Ann, went to fetch water from the family’s hilltop spring. Along the narrow path, two young ruffians, Michael Connelly and William Fitzpatrick, who were residents of Market Street in the section of Fair Haven (dubbed “Dublin”), blocked her way and attacked. She managed to escape and get help, and the pair were tracked down, jailed and tried in April the following year, eventually sentenced to a year of hard time.

Then things took a turn for the weirder. Milton began to build what he claimed would be a 100-passenger, 50-foot steamboat on top of East Rock. Milton boasted, “I could go to Europe in it,” but people suspected that he was building an ark in preparation for a big flood. The boat resembled an oversized sharpie, similar to those used in New Haven Harbor for oystering. But the public curiosity the boat engendered annoyed the increasingly isolated hilltopper, who gave this snippy quote to a local journalist: “I am going to keep it up here till I get ready to take it down, and I am not going to take it down before. There’s nothing peculiar about it. I’ve built two boats up here before this. You’ve heard of boats being built in remote places haven’t you?”

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Milton attempted to move the vessel to the Mill River in July 1883, but he hadn’t properly considered how he would accomplish that task. He first met with failure trying to hoist it down the cliff with cables, later hauling it on wheels down the main driveway and launching it into the Mill River.

Whatever feeling of triumph Milton experienced was short-lived. In 1884, the city condemned his property to clear the way for East Rock Park, taking the land through eminent domain and paying him a meager $13,000 for the entire estate. He reluctantly used that money to build a row of 12 small houses on swampy land along State Street next to the Mill River. He devised an ill-conceived sewage system for the houses based on the rise and fall of the waterway’s tides, leading to the row’s nickname, “Stewart’s Dirty Dozen.”

Milton’s sewage situation combined with his inability to collect tenants’ rent drove him mad—angry, that is. He sued the city, claiming $10,000 for damages caused by a regrading of the street. Meanwhile, at every court hearing, Milton reiterated his claim that the city had robbed him of his East Rock estate. At this time, Milton and his family were living in a house near the base of the rock on Warren Place, where he mournfully dwelled in its cellar. On July 27, 1897, after years of lost dreams, sparse work and poor health, the cantankerous oddball died in bed at age 74, leaving behind his wife and son.

East Rock’s red cliffs now invite all of us to enjoy its natural wonder near the heart of New Haven. As a public park, it gives kids lessons about geology and ecology while students at Wilbur Cross High School play sports along the Mill River on the park’s western edge. From miles away, the Soldiers and Sailors Monument acts as a beacon on the rock’s summit; close up, it commemorates four wars, with the city’s “Angel of Peace” statue at its crown. The park is crisscrossed with trails, and vehicles can weave their way around the rock on English and Farnam Drives, or up it via Hillhouse Drive in warm months.

Take a walk, a spin or a rest on the 366-foot summit with views all around, and imagine that the Miltons had it all to themselves.

Written by Colin Caplan. Image, courtesy of Colin Caplan, depicts a drawing of the Stewart family’s former estate by Thomas Royal Waite in 1887, as reproduced in the April 14, 1912, edition of the New Haven Register.

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