Fall exudes cozy vibes — fireplaces, sweaters, the return of throw blankets – all of which indicate life moves indoors. To some extent, it does. And yet? Regardless of what the mercury reads each fall, it’s beautiful out and Mother Nature puts on her best autumnal show. While fall getaways to New England or Upstate New York may be quintessential, that’s not always in the cards. And there’s no reason to hop on I-91 and I-95 when good old Route 27 has a heck of view (and, this time of year, it’s not of someone else’s bumper in parking-lot-style traffic).
Out East, the fall foliage usually starts with a September prelude — some leaves turning yellow around Tumbleweed Tuesday, before getting into the main event each October. If the wind is blowing you this way or you’re already here and looking for a little outdoor beauty this weekend (or, hey, on your lunch hour!), peep stunning fall foliage at these eight spots around the Hamptons and Shelter Island.
Mashomack Preserve, Shelter Island
This 2,000-plus-acre nature preserve is an oasis within an oasis for resident wildlife and trees. Speaking of the latter, they dress to impress each autumn. See pops of orange, yellow and, of course, red along the red trail. The foliage in the meadow juxtaposes stunningly against browning grass, bushes and an endless fall sky. The light breezes combine with the gentle flow of the creek to provide a natural soundtrack to an adventure worth falling for.
Indian Island County Park, Riverhead
An easier drive for up-Islanders, Indian Island County Park is home to 275 acres of trails — several of which are marked — and shoreline. The park is ideal for an early off-season walk along the beach dotted with fall foliage. Have time to spare? Stop and stay a while — picnic tables make it ripe for a quiet lunch or watching the sunrise on a crisp fall morning with your beverage of choice.
The Long Pond Greenbelt, Sag Harbor to Sagaponack
This unspoiled nine-mile stretch of wetlands, oak forests and ponds runs from Ligonee Creek in Sag Harbor to Sagg Pond in Sagaponack. We likely had the leaf peepers at “oak forests,” which clearly offer all the fall foliage one can shake a (hiking) stick at. You’ll also find around three dozen other rare plants, including sundew and short-beaked bald rush, plus many of the 100 species of birds, many of whom haven’t headed South just yet.


Open year-round, Quogue’s Wildlife Refuge is a for-all-seasons place to explore by foot. Seven miles of trails include forests and ponds offering spectacular vistas for human guests (and wild animal residents). As the foliage falls, it lines the dirt trails and bridges, creating a scene that feels like you’re walking through a whimsical picture book.
Once home to a Native American village, Grace Estate is a natural gem. The main trail winds through an oak-pine forest painted with poppy-hued foliage each fall. The freshwater pond and harbor views make like leaves and pile on the beauty.