Summary
- Shelter Island is a stunning vacation spot with beautiful natural landscapes and scenic hikes that can rival the rest of Long Island’s beautiful hikes.
- The Mashomack Red Trail is a remote and secluded 2.4-mile hike that provides wonderful views of lakes, marshes, and creeks.
- The Coecles Harbor Marine Water Trail offers a unique kayaking experience along the shoreline, providing spectacular views of fall foliage, spring flowers, and local wildlife.
The site of Shelter Island stretches for 27 square miles and is a grand location off the shores of Long Island in New York State. While the island is well-known for having several hotels and fine dining locations, it’s the stunning natural beauty that steals the show.
The Mashomack area is one of the wildest places, where tourists can hope to spot some of the many native bird species and wildlife like turtles while taking lots of photos of the woodlands and lakes. Overall, Shelter Island is the ideal alternative vacation spot for anyone hoping to visit the Hamptons, and its scenic hikes that can rival the rest of Long Island’s amazing hiking trails prove this is so.
Some of the island’s trails are pretty short, but they still take visitors through some amazing places that showcase the land’s natural charm. There’s even a water trail along the island’s shore for truly adventurous visitors. Whether one is staying for a day or several, visitors should not miss out on these beautiful hikes Shelter Island has to offer nature lovers.
7
The Mashomack Red Trail
The stunning secluded trail is one of the island’s longer hikes and takes travelers on a loop back to the Joan C. Coles Trail
Sunrise in the Mashomack Preserve on Shelter Island, New York, NY, USA
The Mashomack Red Trail takes trekkers on a 2.4-mile loop through the park’s wooded areas. This location is known for being more remote and perfect for jogging, cycling, and hiking. It provides wonderful views of the lakes, marshes, and creeks that reach an elevation of approximately 30 yards.
Unfortunately, it is not a pet-friendly trail but a good place to take children. It brings hikers to the beginning of Mashomack Preserve, one of the many places to visit and things to do on Shelter Island.
- Distance: 2.4 miles for the whole loop
- Total Hiking Time: Typically under an hour. Most hikers report it takes around 45–47 minutes to complete
- Difficulty: Easy
6
Joan C. Coles, Red, Yellow, Blue, And Green Loop
This hike is long, but it’s the ideal trail to take to view Shelter Island’s scenic coastline
Beach on Shelter Island, Long Island NY
The Joan C. Coles, Red, Yellow, Blue, and Green Loop is an ideal place to hike to experience the Mashomack Preserve and see some of the island’s coastline. It takes adventurers through the exterior of the preserve, although it’s possible to go off the trail a little and see more of the region. This trail is significantly longer with a higher elevation than the Mashomack Red Trail, even though it also includes parts of this trail.
The beginning loop includes the Mashomack Red Trail but extends further around the park. It’s a popular trail, so visitors will likely encounter other travelers while on the loop. It’s great for outdoor activities, including cross-country skiing and cycling.
- Distance: 7.89 miles
- Total Hiking Time: Between 2 hours and 30 minutes and 2 hours and 35 minutes
- Difficulty: Easy
Unfortunately, this trail does not allow dogs or other pets.
5
Mashomack Red, Yellow, Green, And Jone C. Coles Loop
An excellent,secluded trail at the southern end of Shelter Island near the shoreline
Mashomack Preserve shoreline on Shelter Island between the North and South Forks of Long Island, New York, NY, USA
The Mashomack Red, Yellow, Green, and Jone C. Coles Loop is a beautiful path for exploring the southern parts of Shelter Island and the nature preserve. Similar to the previous trail, this location is longer and travels along the island’s coastline, granting spectacular glimpses of the surrounding waterways.
It’s an idyllic spot for wildlife watching, like bird watching. The pristine and quiet landscape further complements that. This trail is perfect for hiking and running, but unfortunately, they don’t allow dogs.
- Distance: 5.6 miles
- Total Hiking Time: Approximately just under 2 hours to complete, with most hikers saying it lasts around 1 hour and 50 minutes
- Difficulty: Easy
This trail does not permit dogs.
4
The Blue Trail
This trail, part of a larger system, explores both secluded woods and well-traveled paths around Mashomack Preserve
The Shelter Island Windmill in Long Island, New York
The Blue Trail on the east coast of Shelter Island offers unique glimpses of the local wildlife. This trail is so conscientious of the surrounding flora and fauna that travelers are forbidden to run or bike for parts of the path. It’s best to only hike on this trail out of respect for the vast array of creatures calling this space their home.
Bring a camera when walking this trail since Shelter Island is known as a haven for several bird species, including herons, hawks, and osprey.
- Distance: 4.6 miles
- Total Hiking Time: Approximately an hour and a half
- Difficulty: Easy
3
The Coecles Harbor Marine Water Trail
This is the sole trail on the list that provides a starting point for kayaking
A beach landscape at Shelter Island, NY, USA
The Coecles Harbor Marine Water Trail is a one-of-a-kind experience on Shelter Island. Unlike most of the island’s trails, this site requires people to use a kayak or some other small boat to sail along the coastline. While visitors are more than welcome to bring their own boat to the launching point, there are rental shops in the area where tourists can borrow a boat for the day. After all, kayaking the shoreline of Shelter Island is a unique way to spend an afternoon and offers spectacular views of fall foliage, spring flowers, and local wildlife.
One of the places to rent from is Kayak Shelter Island where they provide rentals and tours. It costs $90.00 for singles renting a boat for the day, which is a good option for anyone who wants to take a slower pace and explore the shoreline.
- Distance: 5 miles round trip.
- Total Hiking Time: 3-4 hours for the whole round trip.
- Difficulty: Moderate (because the rowing can be more difficult than a hike)
Be safe and always wear a life vest in the water! For those who do not own one, there are some available for rent at the shop listed above.
2
The Mashomack Red And Joan C. Coles Trail
This simple trail is perfect for beginners and children, and blends two of Shelter Island’s scenic paths
A home on Shelter Island in Long Island, New York, USA
The Mashomack Red and Joan C. Coles Trails blend together perfectly and complement one another very well. While the other combined paths, like the Mashomack Red, Yellow, Green, and Jone C. Coles Loop, take trekkers on a long journey around the island, this trail is quicker. It’s ideal for people traveling with kids thanks to its length and fairly steady incline.
Travelers can choose between walking, jogging, or going off the trail a little to check out the surrounding woodlands. Just be sure not to lose sight of the path. It’s the perfect trail for anyone planning a one-day trip to Shelter Island since there’s so much to see on a Shelter Island day trip.
- Distance: 2.4 miles
- Total Hiking Time: Typically under an hour, with most estimates ranging from 45–47 minutes
- Difficulty: Easy
1
The Laspia Family Trail
Take this short trail for excellent views of the local wildflowers, meadows, and animals
A hilly wildflower field at Shelter Island, New York
The Laspia Family Trail is one of the island’s most charming little trails, designed to showcase its natural beauty. The trail opened in 2018 and got its name from the Laspia family, who worked at the island’s nature preserve for years.
The trail takes visitors on a brief trip near Sanctuary Pond, with informative signs lining the pathway, giving trekkers a brief history of the landscape and the people of the area. It’s a favorite spot for bird watching and spotting wildlife like turtles, but, just like one would respect wildlife while hiking in national parks and protected areas, it’s crucial to do the same on this island as well. Plus, because it’s so short, it’s not the best trail for bike riding.
- Distance: 0.2 miles
- Total Hiking Time: ~10 minutes
- Difficulty: Easy
Hiking on Shelter Island is an adventure located not too far from one of the largest cities in the world, New York City. However, guests would never guess how close they were to the city, thanks to the island’s sprawling meadows, shorelines, ponds, and forests. When visiting this Long Island gem, be sure to explore the above-mentioned scenic hikes on Shelter Island to enjoy its gorgeous landscapes, nature, and quaint charm.
