The best walks and hikes around Shelter Island

Embark on the Mashomack Red, Yellow, Green and Jone C. Coles Loop for a moderate hike that spans 5.5 miles (8.9 km) with a gentle elevation gain of 157 feet (48 metres). You can expect to complete this diverse route in about 2 hours and 18 minutes. As you hike, you will move through dense forests, open meadows, and past tranquil ponds, offering a varied and engaging outdoor experience.

Before you head out, remember that the Mashomack Preserve is managed by The Nature Conservancy, so it is wise to check for any specific visitor guidelines or seasonal hours. Parking is generally available right at the preserve entrance, making access straightforward. Always plan your visit to ensure a smooth and enjoyable time on the trails.

This loop is a fantastic way to explore the natural beauty of Shelter Island, taking you along sections like the barrier-free Jone C. Coles Memorial Trail, which features a boardwalk. You will also pass Sanctuary Pond, a known habitat for various birds and turtles, adding to the preserve's rich biodiversity. It is a great opportunity to connect with nature and observe local wildlife.

Explore the Mashomack Red Trail, an easy hiking route that guides you through a diverse landscape of freshwater marshes, tidal creeks, and serene oak forests. This pleasant path offers intimate views of natural surroundings, including Nicoll's Creek, making it a relaxing outdoor experience. You can complete the 1.7 miles (2.8 km) journey, with its gentle 46 feet (14 metres) elevation gain, in approximately 43 minutes.

When planning your visit, remember that the Mashomack Preserve is generally open from dawn to dusk, seven days a week. However, be aware that during January, the trails are only accessible on weekends. Dogs are not permitted anywhere within the preserve, so leave your furry friends at home. You can also enhance your hike by utilizing a free audio guide available on your mobile device.

Managed by The Nature Conservancy, the Mashomack Preserve is a significant natural area known for its rich biodiversity. As you hike, keep an eye out for the abundant wildlife, which includes wild turkeys and over 200 species of birds. This makes the trail an excellent spot for nature observation and a unique feature that sets it apart in the region.

The Grace Estate offers a delightful escape into nature, winding through a diverse landscape of oak-pine forests and unique kettle-hole wetlands. You'll discover centuries-old cart tracks, pass by the preserve's largest freshwater pond, and eventually reach a historic home site with sweeping views of Northwest Harbor. This easy 3.5-mile (5.6 km) hike, with a gentle 96 feet (29 metres) of elevation gain, is perfect for a relaxed outing, taking approximately 1 hour and 26 minutes to complete.

Planning your visit is straightforward, as the Grace Estate is open from dawn to dusk, allowing flexibility for your schedule. While there are no specific parking details provided, maps are available at the Town Clerk's Office if you wish to explore the full network of Grace Estate hiking trails. This trail is ideal for families and beginners looking for an accessible and rewarding outdoor experience.

Beyond its natural beauty, the Grace Estate holds significant historical and ecological importance. This 516-acre preserve was once home to three Native American villages and later formed part of the bustling port of Northwest Harbor. You can still find remnants of old farmsteads and enjoy birdwatching, with species like ovenbirds and peewees inhabiting the woodlands, making it a rich spot for wildlife at Grace Estate trails.

The Linda Gronlund Trail Loop offers a delightful escape into nature, winding through a diverse landscape of coastal and pine barrens habitat. You'll experience the tranquility of white pinewoods and verdant moss beds, with the trail frequently opening up to panoramic views of Sag Harbor Bay, Peconic Bay, and Northwest Harbor. This easy 3.4-mile (5.5 km) hike, with only 93 feet (28 metres) of elevation gain, takes about 1 hour and 25 minutes, making it a perfect choice for a relaxing outing with stunning scenery.

Planning your visit requires a seasonal access permit for NYSDEC managed lands on Long Island, so secure that beforehand. Roadside parking is available, but always park with care. If you're bringing a canine companion, dogs are permitted on leashes in certain areas of the preserve.

This trail is part of the Linda Gronlund Memorial Nature Preserve, dedicated to a Sag Harbor resident who was a victim of the 9/11 attacks, adding a layer of historical significance to its natural beauty. The preserve's diverse ecosystem includes high-quality tidal wetlands and unique "blow-outs" along the trail that provide expansive harbor views, making it a notable natural area in Suffolk County.