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Walk in the woods through preserved properties

Three summers ago, Susan Carey Dempsey took us on a tour of the Island’s trails through its preserved lands. We thought it was time to get out onto the paths again.

Shelter Island is full of walking trails that many residents and visitors are unaware of. Nearly hidden on the sides of roads, these trails are marked by tall white signs at their primary entrances. Each sign indicates that the trail is part of the Land Preservation Partnership Program, and also provides the name of the trail as well as a QR code that, when scanned, will provide additional information about the trail. A complete list of trails can be found on the Shelter Island Town website. 

The Community Preservation Fund, which was established in 1998, is a public fund based on a 2% transfer tax that the town places on real estate transactions. The town uses these funds to preserve pieces of land from any development. All over the Island, part of these properties are turned into walking trails designated for public use. These trails contribute to local biodiversity, serve as great spots for hiking or picnics, and increase the value and accessibility of Shelter Island’s land.

In August of last year, Councilman Jim Colligan estimated that, together with the Mashomack Preserve, Sylvester Manor and other land purchased with Community Preservation Funds, about 32% of the Island has been kept from development.

One day recently, doused in a liberal amount of bug/tick spray, your intrepid reporter explored all of the trails  as a guide for your ambling pleasure. Get your sneakers out. The trails are calling.

West Neck Preserve

Located between West Neck Road and Nostrand Parkway, West Neck Preserve was acquired by the Town in 2020 to promote freshwater recharge to the West Neck watershed. Since then, this tract has been transformed from unkempt wilderness into a luscious array of pine trees and grasses, hiding many connecting trails. These paths are well-trimmed and mostly clear of overhead leaves so the sky, and nearby trails, are visible at all times. This area is perfect for those looking for a beautiful and easily explorable walking location.

Turkem’s Rest Preserve

Located on South Midway Road, Turkem’s Rest, purchased jointly with Suffolk County in 2006, is a trail that, despite being initially tough to spot, will make for a truly memorable hike. For those who appreciate shade, since it primarily extends through dense woods, Turkem’s Rest is for you. The paths are well cared for, and clearly marked by blue arrows placed on trees. The trail as a whole is relatively short, taking approximately 15 minutes to complete. Toward the end lies its crowning feature, a breathtaking view of Fresh Pond. Here, a wooden bench sits behind an opening in the tree cover, where you can see the pond in its entirety, along with wildlife that happens to be gliding across. This is a perfect trail for those feeling a little more adventurous, and for those who want to avoid the sun on an especially hot day.

Dickerson Creek Overlook Preserve

This preserve, opened in June 2021, can be accessed from the southeastern corner of Grace’s Lane, and contains no hiking trails. Instead, it serves as a small park with tree cover, benches, picnic tables, and an unobstructed view of Dickerson Creek, a place to relax or enjoy a picnic lunch in a beautiful and shady setting.

Mildred Flower Hird Preserve

The Mildred Flower Hird Preserve, opened in November 2019, is in the Village of Dering Harbor, on both sides of Manhanset Road. The entire property consists of approximately 30 acres of land, with hiking trails running all the way through. The preserve is primarily made up of old-growth forest, but is clear enough to walk through without feeling like a jungle explorer. The trails, although sometimes difficult to see, are clearly marked with arrows on trees, so getting lost is not a concern, despite the size of the preserve. This is an ideal spot for hikers who are looking for a slightly longer journey, or those who simply love the feeling of exploring woodlands. 

Old Lima Bean Fields

In the 1950s, Shelter Island was one of the premier lima bean producers in the Northeast. The Island produced hundreds of thousands of pounds of beans until hurricanes, mildew, and the Mexican bean beetle rendered the fields unsuitable for lima bean growth. Now, the property — cleared for walking in  April 2018 — contains a fun trail to hike marked at the beginning by an old red pump, which was used to water the bean fields. Full of unique paths, this walk is a way to literally touch Shelter Island’s history.

Old Nursery Woodlands Preserve

This 24-acre property is located at the geographical center of Shelter Island, and can be accessed near the intersection of St. Mary’s Road and Burns Road. This area’s goal is to be used for passive parkland aquifer recharge, but is also a splendid place to explore. Its trails contain a mix of old nursery stock, dense woodlands, and beautifully maintained open areas. Because there are so many paths to choose from in this preserve, everyone’s experience will be different, depending on which way they want to go. 

Anyone looking for an adventure will find it there, and it’s one of the best trails for wildlife spotting on the Island.