Shelter Island’s history over 10 kilometers: A rundown of sights, places and eras evoked on the course

The Shelter Island 10K course is known for its beauty, but it could just as well be known for the history it traverses.

The 6.2-mile route takes in country views, briny wafts of sea breeze and historical sites that predate the arrival of Europeans; and I’m not talking about the runners who came from France and Germany. Here’s a guide to the 10K course, with points historical as well as topographical.

At the starting line, the Shelter Island Presbyterian Church is just ahead on the left. Established in 1743, the original building burned and was replaced in 1934. What would those 18th-century Presbyterians have thought of scantily clad men and women running past the church on a Saturday afternoon?

Just past the church on the left at .01 mile is the Manhanset Chapel, built in 1890 as part of the Manhanset Hotel, another historical site that the 10K passes at about the halfway point of the race. The Chapel was moved to this location when the rest of the hotel was destroyed by fire.

Across from the Chapel on the right is the building that was once the go-to for Island groceries, the Bohack Store.

The race route heads out of the center of town, with a sharp left onto St. Mary’s Road and continues with a slight but steady uphill to St. Mary’s Episcopal Church on the right at .065 mile. The original church, “a simple box with a steeple” was built in 1873, and burned to the ground in 1892 after a lightning strike. The current church was built in 1893 in a Gothic Revival style.

The route passes through one of Shelter Island’s two traffic circles, and continues on a gradual uphill to a point 1.3 miles into the race. On the right at the crest of the hill is a small red house, 40 Ram Island Road, the Tuthill House. This 1852 farmhouse was built by John Tuthill and remained in the family for a century, long surrounded by a 35-acre farm.

What goes up now goes down. As the course descends, the expansive view that John Tuthill coveted spreads out before you. At the bottom of the hill, the course veers left and uphill on Cobbetts Lane, but if you gaze ahead just before the turn, you see what was once called Factory Road, which ended at an industrial site that sustained the economic health of Shelter Island in the 19th century, the Menhaden Fish Factories.

Menhaden are tiny, oily fish that were cooked down in large cauldrons and used for fuel, fertilizer and for tarring nets. Back in the day, you could not only smell the fish cooking from where you were passing, but you could smell it over half the Island.

Now begins the first significant climb of the course. Cobbetts Lane ascends to the 2-mile mark, and near the crest of the hill on the right is a brick structure, built into the side of the hill, the old Potato House. Once storage for the potatoes grown in great quantities on the Island, it is now a firehouse.

Just past the Potato House, on the right at 55 Cobbetts Lane, is a long driveway, and at the end is the Dering Farmhouse, one of the oldest homes on the Island. Built by Thomas and Mary Sylvester for their son, Henry Packer Dering, between 1776 and 1782, it has a 60-foot-wide, stone-lined well, one of a few such wells remaining on Long Island.

Passing the Dering House driveway, Cobbetts Lane curves up and flattens out into an allée of old oaks and maples starting with the white oak on the right just past Overlook Place, which is thought to be about 150 years old. These trees are a reminder of the importance of Island timber to the barrel construction that was central to transporting goods by ship in the 18th and 19th centuries. Town Historian Lilian Loper (1872-1921) wrote, “A line of old cherry trees marks the almost forgotten site on the South side of Cobbetts Lane of the barrel house.”

A right turn on Manhanset Road leads to an unexpected stretch of deep woods, a haven of shade and shelter that leads into Dering Harbor. As the woods give way, on the left is an enormous Beech Hedge, planted 75 years ago by LaVerne Hench, and one of only two on the eastern end of Long Island. This is the halfway point of the race.

At 3.5 miles the course turns sharply right, around the site of the Manhanset House, a hotel that in its 19th century heyday, was the epitome of the “Gay Nineties.” With rolling lawns, dining rooms, a ballroom and a two-hour direct train/boat service from New York City, it had everything a visitor could want, including a laundry where the fire began that destroyed the resort in a spectacular conflagration in 1896. Rebuilt a year later, the hotel burned again in 1910 and was not replaced. The site is now a private home.

Four miles into the race a small body of water on the left called Julia Dyd Creek joins Dering Harbor on the right as the road dips to just above sea level. Mac Griswold, in her book, “The Manor,” called it, “A poem of a place: woods, water, pasture, sheltered harbor for small craft.” This tidal creek is named for Julia Dyd, a house servant at Sylvester Manor her entire life, whose parents were enslaved there. She lived in a house nearby and died in 1907.

At 4.2 miles, across the street from 54 Winthrop Road, a large boulder sits on the edge of the water. Historian Ralph Duvall wrote that the Native American Chief Pogatticutt used this rock as a throne, and watched the sunset from atop the rock on the last day of his life, in 1654.

At the 4.4-mile mark is a small bridge, called Second Bridge, because Shelter Island has only two. On the left, across Gardiner’s Creek is Manhanset Neck, part of the Sylvester Manor Educational Farm property, and the site of an ancient Native American settlement. As in very ancient. Even older than you may be feeling with almost two miles to go.

Native Manhanset tribes established a small village here that predated the arrival of Nathaniel Sylvester in 1652 by at least 1,000 years. The area looks today much as it did when it was a Neolithic colony, thanks to the fact that the land was owned, and ultimately conserved in perpetuity by the same family since 1652.

From the bridge, the next .4 miles is a tough stretch for tired legs as the course rises and then flattens out to a left uphill turn onto North Ferry Road. The Case Homestead at 141 North Ferry Road is at 5-miles on the right. Best known as the Island’s first central telephone office, starting around 1911, live telephone operators physically “put through” the phone calls of Shelter Islanders with wires, before there were cell towers.

Just past the Case Homestead, the course jogs right and then left past the site of the Thornehaven Poultry Farm, visible behind a tall hedge. Where there was once poultry mayhem, there is now a lovely private home.

The next mile is rolling, passing through Sachem’s Woods on the left. Just shy of the 6-mile mark, a left turn takes you to the finish area on a .02-mile stretch of pavement and then on the grass of Fiske Field to the finish line.

If you leave it all out there on the field, you might make some of your own Shelter Island history.