Beginner-friendly hikes on Long Island
Cold Spring Harbor State Park
“This is one of my favorite spots to recommend to beginners who want a quick but challenging hike. Cold Spring Harbor State Park isn’t large, but it packs a punch with its steep hills and sweeping views over the Long Island Sound. You feel like you’re climbing a mountain, even though you’re still close to town.”
The trail starts right off Route 25A, and after just a few minutes you’re deep in the woods. One of the best parts is the lookout near the northern edge — on a clear day, you can see across the Sound into Connecticut. There are benches along the way and well-worn paths, though it can get muddy after rain.
For first-timers, I usually recommend hiking from the parking lot to the top ridge, then turning around when you reach the southern entrance to avoid the steepest descent if you're not sure of your footing. Just make sure to bring water — those hills will surprise you.”
Best Trail Option: Out-and-back to the upper ridge (~2 miles)
Pro Tip: Go in the morning before the sun heats the hills — and bring poles if your knees aren’t used to elevation.
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Break down:
Distance: 1.8 to 3.2 miles round-trip
Trail Type: Out-and-back
Difficulty: Moderate (short but steep hills)
Location: 95 Harbor Rd, Cold Spring Harbor, NY 11724
Parking: Small lot available at trailhead (fills early on weekends)
Season: Spring–Fall (can be muddy in early spring)
Scenery: Wooded ridge trails, Long Island Sound views, wildflowers in spring
Hazards: Ticks, slippery leaves on hills after rain
Recommended Gear: Hiking shoes, trekking poles for balance, bug spray
SET Tip: Start early and bring water — the hill sections are short but demanding. Use the north-facing side trail for great views of the harbor.Wikipedia+2Parks Guidance+2New York State Parks+2
Map & Resources:
Manorville Hills County Park
“Manorville Hills is a gem if you want space, quiet, and a real taste of wilderness without going upstate. It’s the largest forest block on Long Island and doesn’t get too crowded, which makes it perfect for people looking to explore without the noise of more popular parks.”
The terrain here is rolling but never steep. You’ll hike through pine barrens, past sandy trails and glacial hills. It’s easy to get turned around, so I always tell people to grab a picture of the map at the kiosk before starting — or better yet, carry a compass and use it to practice your bearings.
This park has several loop options. The 2.5-mile loop is a good start. If you're feeling good, you can push to the full 5-mile loop which gives you a satisfying workout without too much difficulty.”
Best Trail Option: Inner loop trail (~2.5 miles) with trailhead near the kiosk
Pro Tip: Bring bug spray, and keep an eye out for white-tailed deer and foxes in the early morning.
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Break down:
Distance: Loops ranging from 2 to 6 miles
Trail Type: Multiple loops and connectors
Difficulty: Easy to moderate
Location: County Rd 111, Manorville, NY
Parking: Main gravel lot near trail kiosk
Season: Year-round (great for snowshoeing in winter)
Scenery: Pine barrens, glacial kames, quiet forests
Hazards: Low cell signal, ticks, occasional muddy spots, Mountain biking trails cross hiking trails
Recommended Gear: Trail map, bug spray, water, sturdy shoes
SET Tip: Download a trail map or take a photo at the kiosk — trails aren't always well-blazed. This is a great place to practice navigation and pacing.
Map & Resources:
Prosser Pines Nature Preserve
“Prosser Pines is one of the most peaceful places I’ve ever walked. It’s a flat, easy loop — less than a mile — but what makes it magical is the towering stand of white pines. It feels like a cathedral built by trees. I bring new hikers here to help them slow down, relax, and just appreciate the natural world.'“
It’s ideal for families, reflective solo walks, or stretching your legs on a quiet afternoon. The light filters beautifully through the trees, and there’s a sense of calm that hits you the moment you step onto the path. No hills, no hazards, just a great place to remember why hiking doesn’t have to be difficult to be rewarding.”
I often encourage hikers to loop it twice and focus on small details each time — the sounds, textures, and patterns of nature here are incredibly grounding.”
Best Trail Option: Single-loop circuit (~0.75 miles)
Pro Tip: Perfect for mindfulness hikes or nature journaling — bring a notebook and slow your pace.
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Break down:
Distance: About 0.75 miles loop (can be extended slightly)
Trail Type: Loop
Difficulty: Very easy
Location: Yaphank-Middle Island Rd, Middle Island, NY
Parking: Roadside parking available
Season: Year-round
Scenery: Tall white pine forest, shaded paths, quiet and serene
Hazards: Slippery pine needles, low light in late day
Recommended Gear: Comfortable walking shoes, camera, water
SET Tip: Great spot for beginner hikers, mindfulness walks, or a peaceful afternoon. Watch for deer and woodpeckers. Loop it twice for more activity.Tripadvisor+6MapQuest+6Avenza Maps+6
Map & Resources:
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