If you find this free trail guide useful, please provide payment by picking up at least one piece of litter on your hike. Cha-ching! Thanks for being awesome! (And here’s a quick primer on Leave No Trace, too, to help us keep the trails nice and fresh for each other.)

Background you can feel free to skip:  I consider Red Wing Recreation Area to be one of the benefits of creating this web site, because I never would have found out about this local gem otherwise. I’d driven by the trailhead a million times without realizing that it was a trailhead at all (though perhaps the cars often parked there should have been a tip-off).

Then Julian Diamond posted a photo to this site’s Facebook page, saying that Red Wing was: “…good for an hour in the woods on a nice day, when time constraints don’t allow for epic adventures. Decent overlook, maybe a 2.5 out of 5 on the ‘scenery’ scale. A couple active geocaches as well, if you’re into that. Just a thought!

And a very good thought at that!


Thank you, Julian! This is the second trail guide I owe entirely to your good recommendations. (The first being High Falls Conservation Area.)

At first, I confused Julian’s suggestion with Red Wing Park in East Fishkill. Turns out, Red Wing Recreation Area is not the same thing as Red Wing Park, even though they are both on Route 82, separated by 6.5 miles. At first, I figured we ran out of names for our parks around here, in the same way we ran out of numbers for our roads (see Rt 9, Rt 9D, Rt 9G, Rt 9W, Rt 9H, and Rt 9N). As it turns out, though, we owe thanks for these parks, among many others, to Red Wing Sand and Gravel.

Thank you, Red Wing Sand and Gravel! Next time I need gravel, know where I’m gettin’ it? That’s right. Home Depot. Kidding! You guys! Seriously, you are my all-time favorite sand and gravel company right now. Thanks for all the awesome parks.

And Red Wing Recreation Area is an awesome park. I’m going to see Julian’s 2.5-star recommendation and raise him another half-star. Who would have guessed that there was a 3-star overlook tucked just around the corner from the busy intersection of Rt 55 and Rt 82 in Lagrangeville? (The official address is Billings, which is apparently a real place, but I’m skeptical. Show me one person from Billings, NY, and we’ll talk.)

The hike I’ll outline below makes a nice loop up to the overlook and back down a different way, right next to an active football field (go Hudson Valley Knights and Hudson Valley Admirals!). I’ve never seen a game in progress here, but if you happen to stroll past when one is going on, you can expect the vibe to be considerably less naturey.

If you wanted to mix things up, there are many access points, trails and options available at Red Wing (though just one money spot, I believe).  Here’s a picture of a trail map posted to a tree in the park (near step #3 below), in case you’d like to check it out for reference (I couldn’t find that same map online, though it may exist somewhere).

If you’re local to the area, the trails and overlook at Red Wing Recreation Area might well be an unknown gem for you, as they were for me. Everyone who likes hiking around here probably already knows about Breakneck Ridge, but I’m guessing a fair percentage of folks, even those who drive right past it regularly, don’t know about Red Wing. If you fall into that category, I hope you enjoy checking it out! You might just find you have a new favorite sand and gravel company, too.

Pooch Proclivity (updated June 2022): Thanks to a helpful discussion in the comments below, we appear to have confirmed that leashed dogs ARE allowed on the trails here, but they are not allowed in other areas at Red Wing.  I suspect that the sports fields are the least dog-friendly areas, since it’s quite common for dogs to be prohibited from sports fields in general.  Please respect any signage you see posted, and otherwise, enjoy your adventure with your pooch!

Trail Guide

Bonus unsolicited advice: Don't depend on having cell service in the woods - it can be spotty out there! Download this trail guide to your phone before you head out. (It's easy to do on iPhone and Android.) May your connection to nature be strong, even when your connection to the internet is weak.

1. From the entrance gate at Rt. 82 (see “Directions to the trailhead” below), army-crawl under the gate (or walk around it, if you prefer), and follow the paved road into the park.

See that cell tower up on the hill?

That’s where we’re headed. Are your loins sufficiently girded? (That’s rhetorical – you can keep the answer between you and your loins.)

2. Follow the road as it ventures away from Rt 82.

In less than five minutes, the road crosses a small (seasonal?) stream. Immediately thereafter, turn left to hop on the trail that runs through a break in a little stone wall.

3. Once you leave the road, the trail dead-ends in a few feet – turn left, toward the creek, to continue on your way.

4. Enjoy the creekside amble for the next few minutes.  (UPDATE March 2019: According to Eero’s comment below, this stretch of trail used to house a railroad that ran alongside Route 82 from the 1800s to mid-1900s.  Interesting!  Thanks, Eero!)

When you come to a fork (five minutes or less after hopping off the road) with a big horizontal log thingie (technical term), take the fork on your right, NOT the fork with the log thingie.

5. Ready to climb that hill? Good! From here, there’s just 400 vertical feet between you and the money spot. Follow the (occasional) red markers up, up and up.

6. Keep on chugging, ignoring any offshoot trails, including the yellow-blazed horse trail that departs on your left in a few minutes.

You’ll see some creative signage around this park, especially on this stretch. If you have your pet bull with you, carrying out his waste in a baggie might not be good enough – apparently, you’re supposed to prevent any bovine elimination entirely.

As a responsible and semi-respectable hiker, I thought some of these signs were a little heavy-handed, similar to the ones in the front of your elementary school bus (riding that bus was a privilege, not a right!). We’ll revisit this issue at the money spot, though, where I found some clarifying evidence about why these signs needed to be hung.

About the time you see a “TRAIL NARROWS” sign, you’ll also notice a gravel road running parallel to your right. This is the road we’ll be taking back down later today.

For now, keep climbing until the trail bends sharply to the left, where you’ll continue to the left, ignoring the road on your right.

7. The trail rises and takes some switchbacks toward the top, dotted with red blazes that guide your way. Feel free to start running in this section, especially if you want to ditch your old, slow dad.

8. In 10-15 minutes from the sharp left next to the gravel road, you’ll arrive, huffing and puffing, at a well-marked intersection, with VELIE RD to your left and OVERLOOK to your right.

Take a right here to head toward the overlook.

9. Just past the “STEEP SIDES” sign, the view begins to open up on your right.

And then, in just another moment, shabwango! (Technical term.) The money spot invites you to grab a seat on this well-placed bench, and to heed the danger of falling off the cliff directly in front of you (some might say the DANGER signs are a wee excessive, but hey, if I owned a park, I’d want as few people as possible to die there, too).

Take several moments to chill with any available homeslices.

The view here is better when the leaves are down, but I wouldn’t classify it as “seasonal,” which would imply that you can’t see diddly during the summer. Even when the leaves are up, the view here is very nice, and you can see clear across to the Hudson Highlands on your extreme right. (Perhaps more importantly, you can see the plaza at Rt 55 and 82 that houses Pizza Express and some other restaurants, in case you’ll be in the market for some grub soon.) Oh, and I see you over there too, Red Wing Sand and Gravel. Thanks for the park!

There’s also a nice picnic table just above the money spot.

Perhaps the most depressing sign I’ve seen in the Hudson Valley rests atop that table.


The bench-tossing apparently happened enough times to warrant creating this sign. If you visit this beautiful place and find yourself with the urge to throw a bench over the cliff, you should first take out your phone, call your parents (or another trusted loved one), and ask them what went wrong with you. Your reception should be good, since you’re standing right next to the cell tower.

For the rest of us non-bench-throwers, hopefully the camera will just capture images of us picking up any litter we might find up there.

10. When you’re done taking in the views and NOT throwing benches over the cliff, walk toward the giant tower just behind the picnic table.

11. Facing the tower, with the money spot directly behind you, you’ll be taking a right to head downhill on the gravel road, following the power lines.

12. As you descend the hill, you’ll see opportunities to hop on a red-blazed trail. To keep things simple, let’s just ignore the Red Trail and keep heading straight on the gravel road.

13. In less than ten minutes, at a left bend in the road, you may recognize the trail from earlier today off to your right. Just ignore it and keep heading down the road, which will bring you to a football field in just another minute.

14. Venture around the gate, past the scenic sheds and dumpster, and hut, hut, hike your way past the football field, sticking to the road.

On your left, a wide meadow opens up, asking why you forgot to bring a kite today.

The gravel road gives way to pavement, then dead-ends back into the road where you started your adventure today.

15. Turn right onto the paved road. In less than five minutes, you’ll arrive back at the Rt. 82 gate.  Welcome back!  Your car missed you.

What a cool place, right? Definitely a local gem. Now, did someone say something about pizza?


Directions to the trailhead:  From the intersection of the Taconic Parkway and Route 55 in Lagrangeville, head east on Route 55. In 1.3 miles, you’ll arrive at the intersection with NY-82. Turn left (north) at the light onto 82. The pull-off is about .2 miles from here – drive past a few driveways on your left, looking for the black gate (which is almost always closed) blocking the entrance road to the park. (Here’s a Google Street View picture of the gate on the left, with Red Wing Sand and Gravel on the right-hand side.) Pull off onto the gate (west) side of the road, parking on the ample shoulder or closer to the gate, leaving room for the gate to swing open, should it need to while you’re adventuring.

Hop out and let the adventure begin!

You can also get directions by checking out the Red Wing Recreation Area entry on the Google map.

Sorta nearby address for your GPS: The address for Red Wing Sand and Gravel, which is directly across the street from the park, is 2332 Route 82, Billings, NY 12510. Google Maps chokes on that address for some reason (at least it does for me), so you can also try:

Rt 55 and Rt 82
Billings, NY

Even though we’ve already established that Billings isn’t a real place, this address seems to work. The pull-off is just a hop-and-a-skip north on 82 from that intersection. (And if you’re from Billings, I mean you and your awesome town no disrespect.  If Billings exists, it is a beautiful place.)

GPS coordinates of parking area: 41.67278, -73.75979 (Clicking will open in Google Maps or the Apple Maps app, depending on your browser/device.)

Resources & Interactives

Super-cool Google Earth flyover of hike route:

Google Terrain Map of hike route:

Alltrails recording of hike (click here to open in Alltrails app or, depending on your device):

Related resources:  If you’re looking for actual facts and/or useful information, visit these resources:

Want to support trails in the Hudson Valley? Here’s one great way: Visit the New York-New Jersey Trail Conference homepage and click on Volunteer, Donate, or Shop! (Then you can volunteer, donate, or shop, depending on your mood.)

Comments (33)

Was this trail guide useful to you? Please leave a comment!
  1. KellyNYC

    Nice hike and steeper than expected! I didn’t see many red trail markers, but your directions were crystal clear. This is a nice spot when you don’t want a full fledged hike, but a nice walk in the woods with some steepness.

    1. Mike

      So glad to hear that these directions were helpful, KellyNYC! Glad you had a nice day out there, thanks for the kind feedback!

  2. Dave

    Disappointed today. Went here to walk with my dog, as I’ve done before, and found out that dogs aren’t allowed anymore. Signs all over the place at the gate. Was looking forward to that scenic overlook. Went to Taconic-Hereford Multiple Use area instead. Nice walk. You may want to consider that one for a future write-up, Mike.

    1. Mike

      That is such a bummer, Dave! Thank you for the heads-up — I’ve posted a warning at the bottom of the “Background” section above based on your input. Appreciate you spreading the word about the new rule to help others avoid the disappointment at the trailhead. Thank you!

    2. Mel

      It seems like dogs and horses are not allowed on the pavement anymore, but still welcomed in the trails on leash. I saw the same sign as you and then moved to the other parking lot where signs are more specific. “No dogs or horses allowed on the blacktop”, “All pets must be on leash”, “Please clean up after your pets”

      1. Dave

        I thought I had posted a follow-up. I went back without the dog and, yes, it appears you can bring them on the trails. In fact, when I returned there was a guy on the trail with his dog and he was not arrested as far as I can tell :-). This park is a perfect example of why Mike’s site is so valuable. Without his directions, I still may be wandering around looking for the scenic overlook. I leaned heavily on the photos and descriptions here. There have been some changes since this write-up was created (e.g., looks like the Velie Rd spur is closed) and there are trail markings of various colors, but they don’t seem to make sense. Still, worth the effort for that view.

        1. Mike

          Thank you all so much for the helpful info and follow-ups! I’ve amended the “Pooch proclivity” warning above to reflect that dogs are indeed allowed on the trails here. That’s great news! (And thanks for the kind words, Dave!)

  3. ruth McGoldrick

    Hi Mike – we use your site as often as possible and have hiked a lot of the trails you have reviewed. We took this Red wing rec trail this past weekend. Really nice. I would note that the red markers are still there. However, someone has added other markers and it looks like the blue marker may very well be the same trail as the red – except more frequent markers than the red. There is also green/yellow but couldn’t figure out where they went as they appeared on and off the marked red/blue trail. Any way great hike. thanks. You can follow us on instagram @deskhikers We are CPAs who mix really nerdy financial humor with hiking the hudson valley! ~Ruth

  4. Mary F

    Went snow shoeing here today. Trail was lovely, never knew this existed. Will come back again. Pleased to find another great walking area, ten minutes from my home.

    1. Mike

      Must have been beautiful out there in the snow, Mary! I drove by this place a million times before finding out there are awesome trails stashed back in there. So nice to have this little gem right nearby. Glad you’re enjoying it! (And thanks again to Julian Diamond for tip, or I’d probably still be driving right by it.)

  5. Alena

    There’s currently trees down across this trail at a few points. You can get around/over them, but it might be troublesome for children/pets. Likely from tropical storm Isaias.

    1. Mike

      I’m sorry I don’t know anything about those trails in Milan, Joseph, but if they’re anywhere near as nice as the Red Wing trails in Billings (if that’s a real place), I’d love to know more about them, too! If anyone has any info on those trails, please let us know!

  6. Steven Estremera


    My company C.T.W. Endurance actually actively host trails races there three times a year, spring summer, and fall including a night 8k in the spring. We are adding a timed trail race there in March as well. But just wanted to let everyone know the course routes are on strava and garmin if you wanted to download the gpx files and run/hike some great trail loops. They are called the Fall Back into the trails 50k/10k which is a 10k loop. the Red Wing Trail challenge is a 10k and 10mi course and the Red Wing After Hours 8k is a 5 mile trail loop. But these are definitely some beautiful trails and we are happy that our events have helped let me more explore them as well as your website here so thank you for sharing it! I have personally marked alot of the diamonds on the course (blue, yellow, orange, green) for our courses and have run the hundreds of miles on these trails so if anyone ever has any questions feel free to ask 🙂

    1. Mike Cunningham

      Please pardon my stupidity. I got quite misplaced today using the online Dutchess county map.
      Exactly how may I access the GPx files?

      1. Mike

        I’m sorry to hear about that, Mike! You can get exact directions to the trailhead described above by clicking the GPS coordinates in the “Directions to the trailhead” section. Would that get the job done? Where did you run into trouble? Let’s get you squared away!

        1. Mike Cunningham

          I found various trailheads. The problem is that I cannot access a decent map showing the various trails that seem to go willy nilly all over the area. I only found the tower and view point because I ran into someone who gave me directions.

          1. Mike

            Indeed, Mike, navigating this park isn’t the most straightforward experience. The closest I’ve found to an official map of this area is the photo posted at the bottom of the “Background” section above, which I uploaded at full resolution in case that might help at all. That trail map used to be posted on various trees throughout the park, though I’ve never found an online version of it. Hope you find that helpful!

  7. Jill

    Thank you so much for the awesome step by step walk through the red wing park. It took the guess work and worry out of going off trail for me. Tell me if there are other trails in the immediate area where you have been able to do the same. Jill

    1. Mike

      Thanks so much for the kind words, Jill! Glad you found this trail guide helpful! I have indeed made a hobby out of writing up the trails around here — you can find the other 79 trail guides here: In the bulleted list at the top of that page, you’ll find a link to a Google Map that has pins dropped on all the trailheads, so you can do a quick scan for others right in this area. Hope that’s what you’re looking for!

  8. Sally Buttinger

    What a lovely surprise to see some familiar faces in these photos! I love hiking this trail and did you know that in the winter you can actually see Camp Hillcroft from the look out! Give us a wave next time you’re up there!

    1. Mike

      And what a lovely surprise to hear from you, Sally! We’ll certainly give you a wave next time we’re up there! And a hug next time we see you in person 🙂

  9. Julia

    Absolutely brilliant guide, not only in terms of precise details and supportive photos but the snark was well worth the read. Hiking is awesome and I am ashamed that I have lived within miles of this trail for years and didn’t know it was here.

    1. Mike

      Thank you so much, Julia! Really appreciate the kind words! I’d never have known about it if not for Julian’s recommendation, either. Hope you enjoy it whenever you get out there!

  10. Venus

    redwing is awesome my dogs favorite place we usually get on the trails at veile road and some times we do the lake trail , creek trail, white trail which is the big loop, the red trail, green trail, yellow traill(easy rider) plus he can go swimming when it hot out and cool off

  11. Jeff Lynn

    I did a loop there today in preparation for the July 9th event. Pretty trail and accurate, detailed description thank you! I parked just outside the gate on the gravel pull off on Route 82, was that correct? Thanks.

    1. Mike

      Greetings, Jeff! I’ve come from the future to answer your question! Yes, that was the right spot 🙂 Just be careful not to block the gate in case a football game happens while you’re out adventuring!

  12. Eero

    Thanks for this hike info! I wanted to point out that the straight flat section you labelled as “creekside amble” was part of the railroad which ran alongside rt 82 in the late 1800’s to mid 1900’s.

    1. Mike

      Greetings, Eero! I’ve come from the very distant future to say, “Thanks for the informative comment!” I’ve updated the trail guide above with that tidbit, and a link down to your comment. Much appreciated!

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