Staff Picks: Favorite Hiking Trails

BY STEPHANIE LICCIARDI, ENVIRONMENTAL ASSOCIATE + GROUP STAFF

It is getting colder out, which means it’s a great time to get outside and enjoy the quiet trails, crisp air, and fall foliage. Here at the Group, we love hiking and finding new trails to explore. We have compiled a list of some of our favorite trails for anyone wanting to get outside and enjoy the fall weather. Wear warm clothes, bring a snack, and don’t forget some comfortable shoes to fully enjoy the beauty of these trails. 

Chatfield’s Hole

Chatfield’s Hole

STEVE BIASETTI, DIRECTOR OF ENVIRONMENTAL EDUCATION: PAUMANOK PATH 

Sag Harbor Express photo: Paumanok Path

Sag Harbor Express photo: Paumanok Path

My favorite local hiking trail is the Paumanok Path, which meanders roughly 125 miles from Rocky Point to Montauk Point. Considering its length, the Paumanok Path visits a great variety of habitats along the way, including the pine barrens, deciduous forest, freshwater ponds, and the tidal coast.

Those freshwater ponds are especially stunning at this time of year, as their shorelines are ablaze in reds and oranges from the changing leaves of highbush blueberry shrubs and red maple and black tupelo trees. To catch these fall foliage displays along the Paumanok Path, try swinging by Sears Pond (Hampton Bays), Big Fresh Pond (North Sea), Long Pond (Sag Harbor), Chatfield’s Hole (Northwest Woods), or Fresh Pond (Hither Woods).

Through the years I had hiked many sections of the Paumanok Path, although not in any organized manner. In recent times I've attempted to walk the trail in a more planned fashion, hiking the Brookhaven section (26 miles) over two days in November 2015 and the Southampton section (51 miles) over six days in February 2018. I just need to find the time for the East Hampton section and the task will be completed!

RACHEL BOSWORTH, MEDIA RELATIONS MANAGER: INLET POND COUNTY PARK

Inlet Pond County Park

Inlet Pond County Park

I always prefer to walk a trail that leads to a beach, or has any type of water view, so Inlet Pond County Park is one of my favorites. It’s a pretty short hike, just about 1.5 miles, but trails will lead you out to Long Island Sound where you can extend your journey a bit. Sadly, I’ve often found a lot of debris exiting the wooded area and heading down to the water. I try to remember to bring a bag to pick up some marine debris to help keep special places like this beautiful. After traversing the beach and trails, I love checking out the bird feeders and surrounding wildlife, thanks to the North Fork Audubon Society. There’s a little something for everyone here!

STEPHANIE LICCIARDI, ENVIRONMENTAL ASSOCIATE: MASHOMACK PRESERVE

Mashomack Preserve

Mashomack Preserve

I visited Mashomack Preserve on Shelter Island for the first time in October and it has quickly become my favorite place to get outside. There is a variety of trails depending on how long you plan on walking and each one provides you with a unique experience! My favorite trail is the longest one, but make sure to give yourself enough time to finish it before it gets dark out. I like Mashomack because you can explore forested land, walk along bodies of water, and learn about native grasslands all in the same hike. You can even see chipmunks running around! It is definitely worth the ferry fare to Shelter Island. 

TARALYNN REYNOLDS, OUTREACH AND EDUCATION MANAGER: DOWNS FARM PRESERVE

Downs Farm Preserve

Downs Farm Preserve

An all season favorite of mine on the North Fork for you, your dog or your family is Downs Farm Preserve in Cutchogue. It’s an easy, shorter hike but makes it a great one to hit when you just need a little time in nature. Take a moment and visit the pollinator flowers in spring and summer, notice the shadbush in early spring through summer and the amazing fall foliage happening right now.

Don’t forget to turn left at the wooden boardwalk and sneak over Downs Creek to an enchanted “island.” From early spring through winter you’ll get an amazing view of the creek and the many wading birds that visit. Continue on the trail until you see a moss bordered trail and follow it for views of the osprey platform across the creek.

Walk the rest of the trail and wind your way through oak forests where birds abound, take your binocs and look for small mammals and deer.

Just a reminder that while this is a dog friendly hike, it is carry in, carry out so please take a waste bag!

Tag us with your favorite Downs Farm Preserve moments, we’d love to see them!

ANITA WRIGHT, ASSISTANT DIRECTOR OF ENVIRONMENTAL EDUCATION: CHATFIELD’S HOLE

Chatfield’s Hole

Chatfield’s Hole

One of my favorite places to hike and view wildlife is the network of trails around Chatfield’s Hole in Northwest Woods of East Hampton. There are many options for hiking loops, and I find the scenery breathtaking! Northwest Woods contains the largest stands of white pines trees on Long Island. I love the soft needles underfoot and towering conifers overhead. Chatfield’s Hole, a beautiful kettle pond right at the trailhead on Two Holes of Water Road, is home to painted and snapping turtles, green frogs and bull frogs, freshwater fish, and is visited by raccoon, deer, belted kingfishers, broad-winged hawks, and much more! And too many wonderful plants to mention here! The trails are popular among dog walkers, so if you do bring your pooch, please pick up after him/her.

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