Poaching the Smiley Road

“Four mile post. Entering the lost community of the huckleberry pickers. You are not forgotten.”

Someone had carved this inscription into a board and nailed it to a tree at mile four, coming from Ellenville, on the Smiley Carriage Road.

Smiley Carriage Road
Along the Smiley Carriageway

Earlier this month, I’d run a loop in Sam’s Point Preserve, partly inspired by Marc Fried’s book The Huckleberry Pickers. The Smiley road figures large in Fried’s book.

In 1900, the Smiley brothers, owners of Mohonk Mountain House and Cliff House and Wildmere on Lake Minnewaska, expanded their already extensive carriage road network with a seven-mile road from Lake Awosting to Ellenville.

One wonders how many guests took advantage of this road: from Lake Minnewaska, it looks to be about a 25-mile round trip to Ellenville and back. Not an insignificant trip in horse and buggy.

The berry pickers who’d been coming up to the Shawangunk ridge since the late 1800s also made use of the road, dubbing it “the Smiley Road.”  I hoped to find evidence of their camps.

Ocean of berries

Starting from Ellenville, the first 1.5 miles of the road are no longer paved or gravel. Runnable and non-technical, the hike skirts Shingle Gully, which is listed on the trail map as off limits unless accompanied by a guide. My friend Gary has been in there and calls it “primordial.” On one side were cliffs, on the other side — well, don’t fall, that’s all I can say.

As I ran, I passed the overturned skeleton of a 1938 pickup truck, mentioned by Fried in his book. At 1.4 miles, the road got rougher, although it was still runnable. It has narrowed from vegetation growth; it was just about wide enough for a vehicle.

At two miles, or as Fried would put it, the Two-mile Post, there was no sign of former human habitation. Indeed, there was precious little land flat enough to pitch a tent or build a rough shack. I kept going through mountain laurels, rhododendrons, and the occasional berry bush. Further up, the road deteriorated to sideways slabs of rock covered with pine needles.

Approaching Three Mile Post, the road widened and the ecosystem changed. Hemlocks and pines abounded, blotting out sunlight. Berry bushes? There were none. The trail crossed a stream, and there was space to accommodate multiple camps. But I saw no evidence of the berry pickers’ camps.

Smiley Road view
View from the road

As I continued upward, the ecosystem reverted to mountain laurel and berry bushes. I passed a rusted mid 50s Buick station, also noted by Fried. It’s shot full of holes by clowns pretending to be the g-men that took out Bonnie and Clyde.

At 3.3 miles, there’s a gate and a big intersection. To the right, the High Point Carriage Road — really more of a trail here. Dead ahead was a smooth, wide gravel road. Some time in the last year, Lake Minnewaska Park Preserve rehabilitated this three-mile section of the Smiley Road, which continues to Lake Awosting. It now has the same surface as the carriage roads near around Lake Minnewaska.

The newer section of the carriage road is up high, where most of the berry picking went on back in the day. There are fewer trees, and the the road is wider than the re-wilded road from Ellenville. A drainage runs alongside part of it. Along sections of the updated road are mountain laurels sprouting among wood chips: some trees were cut to rebuild this section.

From shady to wide open, the contrast between the old and refurbished sections of road is jarring. Some is due to the Shawangunks’ unique high altitude environment, but some is attributable to the refurbished section of the road. Should the road should have been rebuilt? Longtime friend and Rosendale resident Gary thinks the road should be rebuilt straight down to Ellenville, which could become a mountain bike hub.

Vanleuven Memorial sign
Vanleuven memorial

Why wasn’t the Smiley road rebuilt all the way to Ellenville? It may be due to competing administrative bodies. On the trail map, the road crosses Witch’s Hole State Forest, administered by the New York Department of Environmental Conservation. Minnewaska is managed by the Palisades Interstate Park Commission.

A few more minutes running, and I arrived at the sign mentioned above. Another tree had a similar sign, inscribed, “In memory of Richard Vanleuven.”

An obvious herd path caught my eye. Hoping to find more evidence of the berry pickers’ housing, I followed it into the woods. Marked by cairns, it led only to an ocean of berry bushes.

On the other side of the road was a third sign: “Vanleuven camp store.” There was a pile of debris, including a sign for vacuum cleaner sales. An old oil drum and a stone fireplace were nearby.

View to the Northwest
View to the northwest

Back on the Smiley road, I continued another half mile or so towards Lake Awosting. Ursus americanus had traveled the road recently, leaving a pile of scat every few hundred yards. It wasn’t steaming, so he’d had plenty of time to wander into the brush.

Getting to Lake Awosting and back wasn’t in the cards. It’s a 13 mile round trip and I’d been sick the previous week. No point overdoing it. At a height of land, I turned and headed back to Ellenville.

Back home, I searched The Huckleberry Pickers for Richard Vanleuven. Instead, I found a mention of Winslow Vanleuven. Online, census records showed a Richard Vanleuven born in 1935. His father was Winslow and siblings were Roger and Doris. Their reminiscences of life on the mountain can be found in the Shawangunk Journal.

With a couple of decent places to refuel, and the Arrowood Farm Brewery Company a few miles north, Ellenville would make a great jumping off point for your next hike. Through trip from Ellenville to New Paltz, anyone?

13 comments on “Poaching the Smiley Road

  1. Sweet trip, can’t wait to get home to check the maps… Did you see any other hikers on the journey?

  2. I had no idea… The more I learn the more I’m convinced that most of the Hudson Valley south of the Capital District can be interconnected through mostly vehicle traffic free corridors using the old roads and trails and building connector trails from one network to the next. We have an opportunity that very few areas as densely populated as here have, it’s time to start taking advantage of it and build out this network for us that live here and to encourage others to visit in what’s really a very green manner, on bicycles and on foot from the train stations.

  3. ml242, I saw three groups while I was out, but generally had plenty of solitude.

    Tcat001, so far as I’m aware, mountain bikes, and thus fat bikes, are allowed on the carriage roads. To get to the Smiley road, you’d have to set out from Lake Minnewaska.

    Eric: I like the way you think.

  4. Thanks for the trip report.

    I’m told Smiley Rd was built to bring guests from the O&W station in Ellenville up to Minnewaska.

  5. Thanks for the detailed write up. I have done Rock the Ridge twice and really enjoyed these roads.

    Is the Smileys carriage road rideable with a gravel bike starting from Ellenville side?

  6. Murat, the first 1.5 miles from Ellenville are a hiking trail / old road, then you run into the the graveled section. My guess is that it’s hikers only from Ellenville. Your best shot is check with Minnewaska State Park.

  7. There is a hikers only, no bikes sign posted in Minnewaska at the end of the improved part of the carriage road. I hiked down about 1/2 mile and I would say it was plush single track, easy for bikes with front suspension and possible but gnarly on a gravel bike in that part.

  8. I enjoyed reading this–thanks!

    The “no bikes” sign as you head west from Minnewaska into Witch’s Hole is funny. Only about a tenth of a mile past that sign along Smiley Road, you pass into Witch’s Hole Multiple Use Area, where bikes are explicitly allowed (per https://www.dec.ny.gov/lands/103461.html). Why Minnewaska is so adamant about keeping bikes off that 0.10 mile stretch I don’t know. There is also no sign prohibiting bikes if you approach this stretch from the other direction.

    I am not sure whether bikes are allowed on the sections of the road from Berme Road Park in Ellenville to the Witch’s Hole border. I did take a bike up there in January of 2020 and I didn’t notice any signs prohibiting it, but it was mostly dark so I could have missed something.

    Legality aside, ascending from east to west on a gravel bike, there were some sections that were rideable but plenty of hike-a-bike as well. Lots of rocks, some off-camber bits, and some steep grades. I imagine going downhill would be a bit easier.

    Eric: my trip was much as you describe. I took the train to Otisville and rode to Poughkeepsie, mostly (though not entirely) off-road, and mostly unpaved as far as New Paltz. I wrote up the trip here: https://eli.naeher.name/witchs-hole/.

  9. Skied from minnewaska upper lot to berry picker trail via smiley
    I didn’t see a single person for almost 2 hours!
    What a wonderful skating trail with great grooming
    I would love to ski from Mohonk preserve to Sam’s point. I know some younger folk did a longer trip than that this year
    Hopefully we get snow next winter

  10. coverage was very good with no ice. unfortunately the biggest hill on the return trip is on the way back up to the lower awosting. smiley was groomed yesterday not today and probably needs it again tomorrow. i would have loved to keep going to the high point carriage trail if it was tracked and i had the pickup at sams point.
    should be colder tomorrow so not much sun melt.

    the groomers are doing a fantastic job this year i always thank them for a great job

    actually the ruins of some berrypicker huts are on the sam’s point side of the trail

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