Mashomack preserve is located on the very eastern tip of Long Island. It can be a long drive to get out there, but it is a leisurely and relaxed drive through sparse land. The preserve is located on Shelter Island, so you will also need to take a short ferry ride to get over to the preserve. If you go in the summertime, you'll also be lucky enough to be able to check out the farmer's markets while you're out there. The farmer's market that we had stopped at had one of the best local soft cheeses I had ever tried. There are 4 different color trails to choose from depending on what distance you'd like to hike. We chose the red, yellow and green trails. Blue would be the longest at over 10 miles. Another great activity to try in the area would be kayaking.
After the hike, if you drive out a little farther to Orient Point, near the LI ferry, there is a nice beach you can check out. Across from the beach, there is also a small trailhead for a short hike though the woods that leads to the ocean. It is more hidden and thus less populated and a great place for more privacy to relax near the ocean away from the crowds at the beach.
Links: http://www.shelter-island.org/mashomack.html
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