There is a gravel parking lot on the north side of Jericho Turnpike, just west of Woodbury Road, that holds a few dozen cars and charges nothing to park in it. Most people who pull in already know which way they're headed. The mountain bikers turn north. The families with strollers and the after-work walkers head south. Almost nobody treats it as what it actually is: the one spot in Woodbury where three separate trail systems, each with a completely different personality, happen to meet at the same gate.
That gate belongs to Trail View State Park, and the reason it exists at all is stranger than most people assume.
A Highway That Never Got Built
In the 1960s, New York State bought up a long, narrow strip of land through this part of Nassau County to extend the Bethpage Parkway north and eventually connect it to the Caumsett State Parkway. The road never got built. The state sat on the right-of-way for decades under the Department of Transportation before finally converting it into a park in September 2002, a 454-acre linear strip running roughly 7.4 miles between Bethpage State Park to the south and Cold Spring Harbor State Park to the north.
That highway origin explains almost everything odd about the park today. It is narrow instead of broad. It gets cut by cross streets like Woodbury Road at grade, with no crosswalk at that particular intersection, because the land was surveyed for cars, not pedestrians. And it functions less like a park you visit and more like an easement you pass through, which is exactly what one longtime Long Island hiker concluded after walking it: not worth driving to on its own, but genuinely useful if you're already stringing together a longer route.
For Woodbury, that's the point. The trailhead at 8101 Jericho Turnpike isn't a cul-de-sac. It's a junction.
One Trailhead, Two Completely Different Rides
North of that lot, the trail runs through Stillwell Woods Preserve, a 270-acre county-owned tract that Nassau County describes as a mix of old field and oak barrens, habitat more typical of the eastern end of Long Island than the immediate suburbs. This is where the terrain gets serious. A local mountain biking group called C.L.I.M.B. has cut and maintains 13 mapped trails in Stillwell Woods, the longest running 2.5 miles with about 139 feet of elevation gain, which sounds modest until you remember this is Long Island and most of what passes for a hill here barely qualifies. The climbs are short but steep, cut through loose sand and gravel, and one persistent rider review calls the whole loop "a skinny fire road" for anyone used to mountain terrain elsewhere. It's real singletrack by local standards, and worth knowing that trail signage near the northern end restricts that stretch to hiking only, no bikes, even though the rest of the network is built for them.
South of the same lot, the character flips entirely. The trail links into the Bethpage Bikeway, a fully paved, 13.4-mile path that starts at Sunnyside Boulevard in Woodbury and runs down through Bethpage State Park toward Massapequa. It's flat for most of its length, dog-friendly, and built for the kind of ride where you bring a kid on a bike with training wheels rather than a full-suspension mountain bike. One rider crossing describes hitting mile markers painted right on the pavement, a small detail that matters if you're the type who tracks distance.
Here's how the two halves actually compare, side by side:
| North: Stillwell Woods | South: Bethpage Bikeway | |
|---|---|---|
| Surface | Sand, gravel, root sections | Fully paved |
| Distance from trailhead | Up to roughly 8 miles to Stillwell Woods | 13.4 miles to Massapequa |
| Terrain | Short, steep climbs; technical singletrack | Mostly flat, hillier only near the highway section |
| Dogs | Restricted north of the Jericho Turnpike trailhead | Explicitly dog-friendly |
| Best for | Mountain biking, trail running, hiking | Family bike rides, jogging, walking |
Most Woodbury residents only ever do one side. The mountain bikers rarely bother with the paved cruise south, and the family walkers rarely realize the technical loop is sitting a few hundred yards north of where they parked.
The Rules You Learn By Getting Them Wrong
The dog restriction is the one that catches people off guard most often. Bring your dog to the Bethpage Bikeway side and nobody blinks. Cross Jericho Turnpike into the Stillwell Woods trailhead with the same dog and you're technically off the rules, since dogs aren't permitted on that section of the network. It's not clearly marked at a glance, and the split makes sense only once you know the two halves are managed under slightly different rules even though they connect at the same physical point.
The other one is the Woodbury Road crossing itself. Anyone who has hiked the northern portion of Trail View knows there's no crosswalk where the trail meets Woodbury Road, meaning the move is to wait for a gap in traffic and cross on foot, which is a strange thing to have to do in the middle of a state park. It's a small inheritance from the highway that was never finished. You're crossing what would have been an on-ramp.
Who Actually Keeps This Rideable
None of this trail network maintains itself. C.L.I.M.B., the volunteer mountain biking group behind the Stillwell Woods singletrack, hosts a group ride on the first Sunday of most months at 8:45 a.m., open to anyone who wants company rather than riding solo through the sand and roots. Ride-log data pulled from trail-tracking site Trailforks shows October as the single most logged month for mountain biking here, which tracks with what anyone who's ridden it in July already knows: the exposed, sandy sections bake in summer heat, and the tree cover that makes it bearable thins out fast once you get past the wooded core.
If you're walking rather than riding, the calculus flips. Spring and fall mornings are when the old-field and oak barrens habitat in Stillwell Woods is at its most active, before summer humidity sets in and before the crowds show up on the paved Bethpage side for weekend rides.
What This Actually Means If You Live Here
The version of this story most people tell themselves is that Woodbury has "some trails nearby." That undersells it. What's actually sitting a few minutes from most homes in Woodbury is a connected system: a technical mountain bike loop maintained by a dedicated volunteer group to the north, a flat paved bikeway stretching more than 13 miles south, and the whole thing threaded together by a state park that only exists because a 1960s highway plan got shelved. You can walk out, choose a direction at one gravel lot on Jericho Turnpike, and end up somewhere completely different depending on which way you turn.
Most people who've lived here for years have only ever explored one half of it. If that's you, the other direction is worth the turn.
If you're weighing what it's like to actually live day to day in Woodbury, not just what a listing photo shows, Singh's Team can walk you through the neighborhood the way people who live here actually experience it. Get your free home valuation and let's talk about what makes this stretch of Nassau County work for the way you want to live.
