Over the last two weeks, the vibe on Shelter Island has shifted from laid back to energetic, with vacationers and second homeowners enjoying our beaches, restaurants and shops, which in turn sustains our local economy.
I feel a sense of pride seeing the “Roadway Rembrandt” from the Highway Department painting pavement markings for the summer, the pharmacy readying themselves for the onslaught of children vying for their signature milkshakes, and farm stands carefully arranging vases of bright flowers on a Saturday morning.
The starting line is in the center near the library, flowing down the hill to Ram Island Road, near the windmill at Sylvester Manor and 18 Manwaring Road, a business zoned multi-family opportunity for $1.375M. A little farther along, Acorn Cottage at 82 North Cartwright is just before the former Paard Hill Horse Farm, priced at $945K, a sweet 1920s water view bungalow expanded in 2015.
Continuing down the hill is 7 Lari Lane, a 2.3-acre harborfront traditional with its own boat basin for $6.25M. After taking a left onto Cobbetts Lane and a right onto Manhanset Road, one can glimpse the farmhouse with guest cottage and pool at 11 Island Way, for $1.795M.
Then after entering Dering Harbor Village, the route passes 3.1-acre parcel at 6 Dering Woods Road, bordering the golf course, one of the best land values at $599K.
Gardiners Bay Country Club is to the right, where 26 Country Club Drive, a pristine traditional for $1.985M with pool and water views looks over the greens and, a stone’s throw away is 5 Crescent Way, a modernist treetop home with pool and Asian gardens at $995K.
Shortly after, tucked behind a magnificent beech hedge is a traditional on 16 acres belonging to historic Oriole Farms, for $9.75M at 31 Manhanset Road, where the course veers to the right onto Sylvester Road. Oriole Farms’ restored turn of the century boat cabana and deep water dock, one of the longest on the island are prominently featured.
Also in Dering Harbor Village, while running along the waterfront with the estates, one passes 9 Shore Road, a western facing harbor front with a deep water dock, along with an impressive osprey nest and sandy beach. This waterfront, together with the restored 1926 Colonial at 24 Locust Point Road, is offered at $4.675M.
When I ran the 10k in 1996, I trained on the course for months, through rain and snow. The day of the race, my first formal run, there were some mistakes: I lined up at my real time and had to pass slower runners for the first mile; I drank a sugary energy drink that made me light-headed; drank water on the course and got stomach cramps; lost the numbered tear off tab on my pinafore, and not realizing the race continues through the baseball field, I sprinted a little too early and barely had enough in me to cross the finish line.
Although my final time which had been my personal best, was not included in the results, some wonderful sensory memories remain: the adrenaline and breathing from runners around me and the silence of nature just beyond them, the scent of wild roses and salt air along Dering Harbor on Winthrop Road, the photographer on a ladder happily snapping pictures of everyone sweating profusely, the incredible gazelle-like athletes, and the sight of my beautiful dog cheering me on at the finish line.
The 10K is a fundraiser that has provided financial support for Timothy Hill Children’s Ranch, East End Hospice, and the 10K Community Fund, which benefits our community, and includes the Historical Society, Mashomack Preserve, the Emergency Medical Services team, local senior citizens programs, drug education and youth programs, including scholarships to graduating seniors. A special thank you to my clients Ken and Donna Wright, who match these scholarship funds.