Move With John | Nassau-Suffolk Greenbelt Trail | October 18, 2026

Cold Spring Harbor to Uplands Farm: My 6.39-Mile Hike

I came for some hills, a new trail and hopefully a little scenery. I got a solid morning hike, friendly people and a better sense of what I like - and don't like - in a trail.

6.39 milesMy recorded distance

892 feetElevation gain

2 hr 37 minMoving time

Out & backTrail format

Calm water, boats and wooded shoreline at Cold Spring Harbor on the morning of John's hike — Cold Spring Harbor on a clear October morning. Original photo by John Cordeira.

Starting Early, Before the Trail Got Busy

I arrived around 7:30 in the morning and was one of the first cars in the lot. That's how I like to start an outdoor adventure: getting there early enough that things are still quiet and I can settle into the walk without a crowd around me.

I followed the Nassau-Suffolk Trail from Cold Spring Harbor toward Uplands Farm Sanctuary. It was hilly enough to give me a workout, but it wasn't the kind of climbing I'd experienced on my Bear Mountain hike. I stopped at a few spots along the way to eat, look around and take photographs. Later in the morning, I started seeing more hikers.

Something I noticed was how friendly the hikers were. People seemed more inclined to acknowledge one another on this trail than they had at Bear Mountain. It didn't make the hills any steeper or the views more dramatic, but it was a nice part of the morning.

John Cordeira on the Nassau-Suffolk Trail amid October foliage at Cold Spring Harbor — Out on the trail. The trees were beginning to show their October color.

Timber Steps, Open Woods and My Bear Mountain Comparison

I'm still pretty new to hiking, and I'm learning what catches my attention. One thing stood out on this route: some of the uphill sections were built with timber trail steps - wooden risers with dirt inside them. They're practical, but visually I prefer the large, rugged dry-laid stone steps and boulder staircases I saw at Bear Mountain.

The stonework feels heavier, stronger and more like it belongs in the terrain. Bear Mountain's woods also felt denser to me. Here, the forest was more open, and even with the elevation changes I didn't get the same sense of drama.

That isn't a criticism of the people who maintain the trail. It is simply what I enjoy when I'm out there: natural stone, rugged ground, more dramatic scenery and a route that keeps surprising me.

Small wooden footbridge and rustic bench surrounded by autumn woodland along the Nassau-Suffolk hiking route — A wooden footbridge and a rustic bench along the wooded route. Photo by John Cordeira.

A Little Smile Along the Way

One photograph I had to take was a stone with a simple smiling face tucked beside a tree near the timber steps. I have no idea who put it there or what its story is. It was just a small, unexpected thing I noticed while walking.

Not every trail gives you a huge overlook or a spectacular moment. Sometimes there's a wooden crossing, a quiet spot to stop, or a funny little rock that someone left behind. Those are worth noticing, too.

Small smiling-face rock beside a tree and timber trail steps on the Cold Spring Harbor hiking route — No backstory from me on this smiling rock - it just caught my eye.

One Thing I'd Change: Give Me a Loop

This particular hike was out and back. After going in one direction, you turn around and retrace the same route. I understand why people like that format, but I'm finding that I prefer loop hikes. I like the idea of covering new ground throughout the entire walk instead of seeing the same trail on the return.

I'd still call Cold Spring Harbor a worthwhile morning. I got my distance in, had decent elevation, spent time outside and enjoyed the harbor area. But was it breathtaking? For me, no. I wouldn't rush back to repeat this exact route. I'd rather find another trail I haven't explored yet, preferably one with steeper climbs, more rugged scenery and a good loop.

Peaceful Cold Spring Harbor waterfront with moored boats and wooded shoreline — The harbor itself was a peaceful sight. Original photo by John Cordeira.

My takeaway: 6.39 miles and 892 feet of climbing made for a good workout. The friendly hikers were a pleasant surprise. But I'm learning that rugged stonework, changing scenery and loop routes are what really make a hike memorable for me. The search for my next one continues.

How This Trail Connects to the Neighborhood

As I walked, I noticed houses near wooded parts of the trail. That's interesting to me for another reason. I'm a Long Island real estate broker, and I've spent more than 20 years helping people buy and sell homes here. Seeing a trail close to residential areas got me thinking about what living near this kind of outdoor space might actually be like.

It's easy to focus on a home's interior and overlook what is outside the front door. Nearby parks and trails can shape how you spend your mornings and weekends. Of course, living near a preserve doesn't automatically mean a property has private access or backs directly onto protected land; those details have to be checked for each home.

Cold Spring Harbor is a Suffolk County hamlet in the Town of Huntington, and hiking here inspired me to research the surrounding neighborhoods, homes and local history. That's how I like to build my guides: starting with real experiences, then doing the research instead of pretending I already know everything. You can now explore the Cold Spring Harbor Real Estate & Local Guide and my local parks and trails guide.

Explore Long Island Living With Cordeira Homes

I'm John Cordeira, Broker/Owner of Cordeira Homes. I know a home is more than a floor plan. The parks, trails, waterfront and everyday surroundings matter, too. If you're thinking about buying or selling on Long Island, I'm happy to help you explore the bigger picture.

Explore Cold Spring Harbor Homes Find Your Cold Spring Harbor Home Value

Thinking of selling? Or contact me directly.

Planning the Trail for Yourself

New York State Parks describes Cold Spring Harbor State Park as the northern trailhead of the Nassau-Suffolk Greenbelt Trail. The Nature Conservancy's Uplands Farm Sanctuary connects with the longer trail system.

My numbers above are from my own recorded hike. Your mileage and ascent may differ depending on how far you walk or where you turn around. Check official trail maps and posted access rules; wear footwear suited to uneven or slippery ground, and watch for ticks.

Cold Spring Harbor Hiking FAQs

Is the Cold Spring Harbor to Uplands Farm route a loop?

The route I hiked was out and back, not a loop. I prefer loops, so that's something I'd consider before choosing it again.

How difficult was the Nassau-Suffolk Trail here?

I'd call my hike moderate. I recorded 892 feet of elevation gain over 6.39 miles. There were hills, but I found Bear Mountain significantly more rugged and challenging.

How long did your hike take?

My moving time was 2 hours and 37 minutes. I stopped at a few spots to eat, look around and enjoy the surroundings.

Can you live near hiking trails in Cold Spring Harbor?

Some residential areas are near the park and trail corridors, but exact lot boundaries, access rights and distance to trailheads need to be verified for individual properties. My Cold Spring Harbor real estate and local guide explains more about nearby neighborhoods, schools, trails and homes.

« More adventures on Move With John

John Cordeira
Broker/Owner, Cordeira Homes
More than 20 years helping Long Island buyers and sellers
#RippedRealtor