Best Long Island Day Trip Near Me: Shelter Island

Shelter Island is accessible only by boat; it’s about a 10-minute ferry trip from Greenport or Sag Harbor. If you’re driving, take the LIE out to Riverhead, then head north to Greenport or south to Sag Harbor — the distance is roughly the same. A one way trip on the ferry with one car, one driver and one passenger is $13.

Shelter Island is a secluded 8,000 acre island on the eastern end of Long Island in New York. It is surrounded by Shelter Island Sound on 3 sides and Gardiners Bay on the 4th side. Nearly 1/3 of the island is owned by the Nature Conservancy. There are plenty of beaches, restaurants and hikes along the island.

Click HERE for a brief history of Shelter Island, NY.

We arrived on Shelter Island a little before noon. We headed straight to Mashomack Preserve. This preserve has 11 miles of coastline and acres of interlacing tidal creeks, mature oak woodlands, fields, and freshwater marshes. There is an accessible 1 mile trail; and 1.5, 3, 6, & 12 mile loops. There is also a marine water trail. Open daily July & August, closed Tuesdays in Sept-June, and open weekends only in Jan.

We decided on the green trail which took about 2.5 hours from start to finish, including a peanut butter and jelly break. The red trail goes through the woods, the yellow trail travels through a beautiful field with wildflowers, butterflies and hawks. The green train follows the coast for half of it and then back through the forest. Half way through the green trail we stepped off onto the beach and ate our picnic lunch on a rock. On the beach path there were crazy wasps coming out of holes in the ground carrying larger insects. Watch out for them!

Three must haves for this walk: water, snacks, BUG SPRAY with deet. Check out OluKai for great walking shoes & sandals.

We were super hot and sweaty after the hike. We drank a lot of water, changed into swim suits in the car and headed to the beach! The closest beach is Wades Beach, a beach with stony shell sand and gentle waves. There is a lifeguard and a swim area. It felt sooooo good to jump in the water after a 2 hour hike. The only downside to all of this is we came back to a $100 parking ticket! Apparently you need a permit to park here.

We went to Sunset Beach for sunset. The Sunset Beach Hotel/Restaurant is a great place to have a cocktail across from the beach. This hotel was closed due to COVID which was disappointing.

We found live music at the Shipwreck Boat Bar overlooking the West Neck Harbor. Built in the 30’s the twin mast vessel roamed New England and was later used in the Great South Bay harvesting oysters and clams. Once retired, it was stocked with a beer keg cooler as well as a full bar.

Salt restaurant is a dockside restaurant next to Shipwreck Boat Bar overlooking Menantic Creek. The frozen mudslides are awesome! The wings and lobster roll are great.