Into The Woods: Great East End Winter Hikes

Pictured Above: On the Black Owl Loop in Flanders

When winter comes, the woods beckon.

As the notion of a walk on the beach conjures up a biting chill and a windburned face in these coldest months of the year, the appeal of a walk through the East End’s woodlands is difficult to beat. 

It’s a mostly tick-less season, where you can see the lay of the land through the leafless trees, a season of clear blue skies and hard, easily trod ground, made a feast for the eyes by the crackle of frosted leaves, or a light powder of snow on the ground. As an added bonus, the trees provide a great break against the hefty winds that rock our shoreline.

We’re also lucky to have so many well-kept trails on the East End. There’s no way we could list all of the gems to be found out there, so, by all means, go exploring. Here are a few of our favorite short hikes to get you started:

Black Owl Loop, Flanders

The trailhead kiosk here is tucked just off of the south side of Flanders Road on Spinney Road just east of the light at Long Neck Boulevard. This trail is at the eastern edge of Long Island’s Pine Barrens, a rare ecosystem of pitch pine and oaks that conceals the greatest diversity of plant and animal species in New York State.

You can walk what seems like forever in here — the 5-mile Black Owl Loop intersects the Paumanok Path, which goes from Wading River to Montauk — getting lost in your mind as you pass by Owl Pond and then Sears Pond, following the yellow blazes through swampland and past kettle holes created by the retreating glacier that formed Long Island, upland to sweet, soft, needle-covered ground.

This trail is also a favorite of local trail groups, who organize quite a few group hikes here this time of year.

Sound View Dunes, Southold

This 57-acre park off of Soundview Avenue is just west of the Peconic Dunes 4-H Camp, with a kiosk and parking area on the north side of Soundview Avenue.

Acquired by Southold Town in 2008 from the Bitner family, this park is host to a rare maritime freshwater interdunal swale, a shallow freshwater wetlands set just back from the dunes. The 1.6 mile loop takes you araound a hidden lake, hugging the edge of the interdunal swale, before depositing you on a stunning Long Island Sound beach. While the beach can get cold on winter days, its easy to duck back down the trail and get back to your car to warm up after a brisk and invigorating hike.

Seal Haul Out Trail, Montauk

There was a time on the East End when seal sightings were rare, but that’s no longer the case, as seals have taken up winter residence along the rockiest parts of our coastline, particularly here, in Montauk. 

Park on Camp Hero Road on the south side of Montauk Highway, and walk across the street to find the trailhead for this .9 mile trail (1.8 miles in-and-out), or make it a loop by adding in a hike around Oyster Pond, with stunning views of Block Island Sound, after you leave the seal observation station.

The Walking Dunes, Napeague

Another of our rare ecosystems, The Walking Dunes in Hither Hills State Park was a forest of pitch pine and oak along Napeague Harbor that is now buried under sand as a dune moves southeasterly through the area. This eerie landscape, also called “The Phantom Forest,” changes from year to year, and can be accessed at the end of Napeague Harbor Road. The trail is 2.7 miles long. This has historically been a great wild cranberry picking site, but word got out and now cranberries are few and far between.

Inlet Pond County Park, Greenport

This 50-acre park at 64795 Route 48 is also home to the headquarters of the active North Fork Audubon Society, and as you travel its trails, you will see that it is a beacon for birds. The well-maintained 1.6-mile trail here leads through woodlands to an observation platform over the freshwater inlet pond, a great place for birdwatching and picnicking. The trail continues out to a Long Island Sound beach that can be cold in winter but is well worth bundling up for.

Quogue Wildlife Refuge, Quogue

The Quogue Wildlife Refuge is an oasis from the world, nestled around a former ice pond at 3 Old Country Road in Quogue. Any meander around the pond, or up through the dwarf pine plains at the north of the refuge, or through the Fairy Dell to Quantuck Creek is bound to do your soul good. 

Cap off your visit by watching the birds on the ice pond from the vantage point of numerous benches and overlooks, or from the Nature Center on a particularly cold day. The refuge rents cross-country skies after snowfalls, and will be holding its annual Light the Winter Night illuminated trail walk on the evening of Jan. 25.

Mashomack Preserve, Shelter Island

You can pick just about any hike through Shelter Island’s 2,000-acre Mashomack Preserve at 79 South Ferry Road and have a great adventure. The trails are all well-marked and maintained, with loops ranging from 1.5 to 12 miles, and designed to give you a great feel for the ecological diversity of this special place, meandering through meadows, wetlands, woodlands and alongside the Peconic Bay. Note Mashomack’s trails are only open on weekends in the month of January due to shotgun hunting season, which runs Jan. 5 through Jan. 31 on designated lands within Suffolk County.

Husing Pond Preserve, Mattituck

This trail, maintained by The Nature Conservancy is a quick jaunt, and you really can’t call it much of a hike, but it’s a welcome dose of nature on a cold day or if you want to squeeze in some outdoor time on a break from work. The trailhead is easy to miss — it’s across the street from the Mattituck Park District beach, baseball field and the Mattituck Yacht Club at 9462 Peconic Bay Boulevard in Mattituck. Park by the baseball field, cross the boulevard, and you’ll find the trailhead kiosk just east of where you parked. Hike in to a promenade overlooking the pond and spend a few minutes in quiet contemplation.

There are no right or wrong trails out there. The important thing is that you get up and go out exploring, even when the weather has you wishing you were in bed.

— Beth Young