We love to Knock Around and ride our bikes on the Henry Hudson Trail

The Henry Hudson Trail, like others in the “rails to trails” network, is a combination of former railway paths that cut through the Monmouth County region. It offers many different views, as it passes through both natural and urban, man-made settings.

Some accounts state that the trail is 22.6 miles long, while others list it as 24 miles long. What I can tell you is that I did the entire length of the trail, from one end to the other – starting in Freehold and ending in the Atlantic Highlands – with a friend in 2020 and it was 25 miles.

Melissa and I have ventured off to ride portions of the Trail at various times, especially since a good part of it is in close proximity to our estate in Old Bridge. I tried to convince Melissa to do the entirety of it with me. And she was game. But it’s not as easy as you might think.

That would be a huge task as we would have to take two cars, park a car at one end, and then go with the bikes on the second car to the other end, ride back to the first car, load the bikes back on the car, and then drive back to get the second car. Eh…it’s a bit too much work. Unless, of course, we road it back and forth – 50 miles – but THAT was never going to happen.

But the solution was simple….let’s just break it up.

Because although it is considered one trail, it is not continuous. It is broken up in two places – in Marlboro and Matawan – creating three separate and distinct sections. In order to do the Trail in its entirety, you CAN brave the streets for a distance to connect the three sections.

It’s in Marlboro that the Trail is interrupted and there is approximately a two-mile stretch on Route 520 and Route 79 to get to the next section. Not exactly the safest ride. Then in Matawan, you again have to ride along the main road to get from an abrupt end in a residential neighborhood to the next trailhead in Keyport. Again, not the safest of rides.

So we decided to do each section – back and forth – on different days.

The Southern segment runs from downtown Freehold (Route 537) north to Route 520 and Big Brook Park in Marlboro.

We parked at Big Brook Park which is right on Route 520. It has a nice-sized parking lot and even has a port-o-potty in the lot.

The Trail begins in Big Brook Park and meanders through some park lands before it heads into a beautiful tree-lined path. There are some ups and downs and a couple of streams. It takes you through the towns of Freehold Township and Marlboro.

While there are a number of cross-overs, where you have to cross local streets, the main break is at Kozloski Road. Luckily you just have to cross at a main intersection, riding a sidewalk on either side, rather than actually riding on any street.

Other than that, there are some beautiful streams, nice wooded areas, and even some very old buildings along the way…all while paralleling Route 79 off in the distance.

Now Melissa has to be mentally prepared for any distance. And when I checked to confirm the distance, it kept coming up as 3.3 miles one way. And I showed it to her. But it was NOT 3.3 miles. It was 5.82 miles…11.75 miles round trip.

Alan: Melissa…what’s the matter?

Melissa: Why couldn’t you just go out by yourself and check it out…like Magellan! HE went out and came and reported back. That’s what YOU should have done.

The Northern segment stretches from Wyncrest Road right on Route 79 in Marlboro and basically runs parallel to 79 until it meets a dead end in an old neighborhood in Matawan.

We have done the Northern or “middle” section a number of times as the one trailhead is VERY close to the house. That trailhead is actually on Station Road, yet the trail itself restarts on 79 at Wyncrest Road.

We park in a lot behind an office building directly across from the trailhead. But don’t tell anybody. You’re not really supposed to do that but the lot is always empty and, truthfully, there really is NO PLACE TO PARK at EITHER end of this section.

The section of trail runs through the northern part of Marlboro, through some wooded areas that border residential and commercial properties, and then some desolate area that appears to be some easements housing towers with high tension wires (check for radiation afterwards), before hitting Aberdeen (where you cross over 79 on the street) and Matawan (where you cross over Route 34 via an old bridge…an actual bridge not the town).

On the way you get to pass by an old Stewarts and you can grab yourself a root beer float.

After going over Route 34 you pass by a housing complex and then into the middle of an old neighborhood of tiny bungalow-like homes and then…THE END! It just abruptly ends.

If you are intent on completing the entire trail, you then have to backtrack and take Atlantic Avenue and some other main roads over the Garden State Parkway and into the parking lot at the Keyport trailhead, about another two miles on the streets.

Of course, we weren’t doing that and turned around to head back after 4.85 miles. So that section was just under 10 miles round trip.

The Atlantic section goes from Keyport to the Atlantic Highlands and is the longest distance, at about 12 miles, and it is probably the most unappealing of the three sections.

It takes you through Keyport, Union Beach, Hazlet, Keansburg, Middletown Township, and the Atlantic Highlands, basically hugging Route 36 most of the way.

We ended up breaking this section up into two rides. And really it was because of the weather both times.

On the first attempt, we began in the Atlantic Highlands, and figured we would go north and turn back in Keyport. But it started raining, the skies were dark and it was windy. So we went about 5 miles and turned back…10 miles round trip.

For the second try, we began at the other end, in Keyport with the intent on heading south. And we had every intention of going the distance, but it was cold and VERY windy. It wasn’t going to be fun. So we rode seven miles, to the point we had reached riding from the other direction, and turned back.

The scenery is somewhat nice as you go through neighborhoods in Keyport, Hazlet, and Union Beach. You can even make out the New York City skyline off in the distance.

Then there are some areas in Keansburg that are nicely wooded but also parts that are very sketchy. Going along the parking lot of a bar is not appealing at all, especially when vagrants are hanging out in the vicinity. I have ridden the section multiple times and I would never want my daughter out there by herself.

The sections in the Middletown neighborhoods are very park-like, if you can manage to tune out the traffic noise from Route 36.

After passing by EARLE Naval Base, you can even see the Quick Stop deli where the movie Clerks was filmed right from the Trail in Leonardo.

Melissa enjoyed the other sections more.

Alan: We have only 2 miles to go.

Alan again: We are at 1.5 miles.

Melissa: I don’t give a FXXX! I don’t need to get an update every tenth of a mile. I just want to see the FXXXING CAR!

The Henry Hudson Trail is, in fact, paved, some of it fairly freshly paved. But there are still some raised spots thanks to the many roots systems underneath that make for a sometimes startling bumpy ride. It’s mostly a very flat ride, but there are some minor inclines that will take some effort. But for the most part, it IS a very easy and fun ride.

Each of the sections has its good and bad points. There are a lot of wooded areas and some nice picture spots if you like nature. But it WAS an old rail trail…a railway that passed through farmlands, which became residential neighborhoods and industrial businesses. So you are truly riding in what could be considered someone’s backyard. At least it might seem that way.

It is VERY family friendly too. There are a lot of young children riding along with their parents, as well as people running (because it IS a perfect place to get your miles in) and walking their dogs. Another thing we noticed is that there are quite a number of blue emergency call boxes that have been placed in parts of the Atlantic section. And so far it is only in those areas.

If you have the time and energy, pack a lunch, and spend some time pedaling along and taking in the sights along the Henry Hudson Trail. Whether you decide to do it all at once, or in sections, it is definitely one of the natural wonders and highlights of Central Jersey.