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The North Ferry terminal in Shelter Island Heights is where our journey starts. (Credit: Grant Parpan)

A stroll through Shelter Island  Heights may not be a long walk, but thanks to the neighborhood’s famed hills, it’s one that will challenge you. 

Starting from sea level, in the North Ferry parking lot (it’s $3 roundtrip to walk on the ferry from Greenport), you can take a walk up the brick pathway that crosses Prospect Park. This grassy public space marks the site where the legendary Prospect Hotel stood, an elegant structure built in 1872, which dominated the hilltop until it was destroyed by fire in 1942. There are still scorch marks to be seen on the trees rimming the park from the intense heat of the fire.

The brick pathway is a fairly new addition; many of the bricks are etched with names of residents of the Heights. Several residents have memorialized the parents and grandparents who first brought their families to the Island.  

Continuing up the path, there’s an archway of hedges that has grown in toward the upper end. In spring and summer, blooms will crown this arch with fresh and gentle color. At the top of Prospect, as you face the famous Gingerbread House with the tilted tower, you can choose a path to explore, instead of continuing up the main road, Grand Avenue. 

A quiet dawn at Union Chapel in the Grove. (Credit: Martin Burke)

Historic Heights

Turning right on Bay Avenue, you’ll walk a few blocks, then turn left on Wesley to where the Union Chapel in the Grove stands. Built in 1873, its famed stained glass windows by Islander Walter Cole Brigham were installed in the early 1900s, using quartz rocks, oyster and scallop shells from Island beaches, as well as opalescent moonstone from Orient. Although the church is closed for the season, you can admire the windows and the exterior before continuing up the hill. 

Most of the houses you’ll pass in this historic district harken back to the time when much of the Heights was a Methodist summer colony. The Victorian gingerbread styles of the houses imitated the canvas tents pitched at the religious meetings beginning in 1872. The Chequit, which is now a hotel and restaurant next to the Pharmacy in the Heights, orginally served as a communal kitchen and dining room for the members of the congregation.

At the top of Wesley Avenue, turn left toward Our Lady of the Isle Roman Catholic Church. Stories say that well-to-do residents built the church in 1872 so their servants wouldn’t have to go to Greenport to worship.

A house in the Heights, representing the Island’s welcoming spirit of the season. (Credit: Eleanor P. Labrozzi)

Well-loved, divine homes

Continuing up the hill on Prospect Avenue, you’ll come upon a shark — a giant stone shark diving through a grassy hill as if it were a mighty wave. It’s a Heights landmark that’s been in place for decades.

Next, on the right, is Aquarelle, Olive Reich’s home and studio high above the bay. Here she has captured the light and inspiration of her environs in her classic Shelter Island paintings. Further up the hill, the house next to the Reich’s is one where my family spent a few summers. I’ve never forgotten the views from the wide back porch on summer evenings, far past the North Fork to where the edge of Connecticut was just visible. 

The house was built in 1884 by Dr. Richard Salter Storrs, pastor of the Congregational Church of the Pilgrim in Brooklyn. A famed orator, he delivered a two-hour funeral eulogy for Abraham Lincoln, and in 1886 the convocation for the opening of the Brooklyn Bridge. The Storrs built a house next door for their daughter, who had married a minister. The presence of these clerics led to the name Divinity Hill, which it still bears.

You are almost at the crest of the hill and you may well be feeling it. If you wish, you can turn around and head back, maybe picking a different road to explore on your way down to the ferry. If you turn left before Our Lady of the Isle, you can follow Bluff Avenue, where houses are perched high above the bay, then take Waverly Avenue back toward the Chequit, and Spring Garden back to Prospect.

The clubhouse of the Shelter Island Country Club. (Credit: Eleanor P. Labrozzi)

Highest of the heights

Or you can continue up Divinity Hill a bit further to where Bayview Avenue turns off to the left, through roads lined by thick woods. In winter, you can see some houses much more clearly than when summer greenery blocks the view.

You can turn left on Tower Hill Avenue to come to the triangle by the Heights Firehouse, or continue on Prospect Avenue until you reach Goat Hill, the Shelter Island Country Club’s golf course. The clubhouse sits atop one of the tallest spots on the Island, and the view is always impressive. Follow Sunnyside Avenue back toward the business area of the Heights.

Whichever path you choose, you will wend your way eventually back down toward the ferry. When you catch your first glimpse of the harbor from the top of Prospect, you will remember how Shelter Island can take your breath away. It’s your moment of beauty, at the end of your walk, and you’ve earned it. Take the time to savor it.