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Woodstock, NY

In December of last year, in the thick of a pandemic and in the craziness of the holidays, I took a trip to Woodstock to get away from the world. I had been meaning to go visit the northern New York town because it was where my mother grew up. Having been once when I was young, I have one of my earliest memories there. And there was no time like December of last year to have an adventure in Woodstock, NY.


Hard to describe what it is about the history of where you come from that becomes so important. Amazing people can come from anywhere, right? Doesn't matter where you are from. And that's true. But even so, I think one cannot help but attribute who one is from where one is from. This sentence is the non-comic relief after a rather oddly existential statement in a particularly casual blog. In Woodstock, it's incredible how much history is in the small town. The town is only one strip, populated with small businesses and restaurants that exude character. From the toy shop to the Christmas tree in the center of town, it feels like you should be in a hallmark movie and your bus has broken down on the way to NYC. It emulates a world so different from my everyday life in Washington, DC.

The Cottage

The cottage that we stayed in took some warming up to. It suited us in the short weekend we were there. And it was on the Monday after that it snowed. Snow always shocks me how entrancing it is. It truly changes the landscape and environment.

The cottage taken on Rollei CR200 expired film.

The shed on the property. Shot on Ilford HP5.

The scene from inside the cottage.


Overlook Mountain / Karma Triyana Dharmachakra

The entire landscape around Woodstock has a ton of character. The farms seem to each have either a Little House on the Prairie vibe or a Davy Crockett aspect to them. Woodstock is a small town with a true small town heart despite it being so famous. Overlook Mountain continues the theme of uniqueness with its own history. At the base of the climb resides the Karma Triyana Dharmachakra, a Tibetan Buddhist monastery. Surrounded by Tibetan prayer flags, the monastery demands a reverence in the air.

The road in between the monastery and the base of the hike.

Tibetan prayer flags have strewn over a dying tree.

The hike leads to a steep climb that doesn't give much of a view. Further still, on our hike, heavy fog set in, which actually gave the hike a rather adventurous feature.

The snow spotted grounds as the fog set in.

Slightly further in the journey, the fog had blanketed the air making the treetops hard to see.

The old sign directing to the fire tower that still remains at the top

At about the 2-mile mark of the 2.3 miles up the mountain goes past a group of abandoned buildings that once harbored vacationers wishing to lodge on top of Overlook Mountain. The ruins are rather haunting.

Fallen trees in the fallen ruin.

The entrance of a once glorious hotel. Shades of a horror movie throughout the ruins.

Once you get to the top of Overlook Mountain, one would normally be able to see for miles looking over the Catskills. The fire tower specifically built to look over the mountains to pinpoint forest fires.

Heavy fog hiding the fire tower.

A storm started just as we reached the top. The fire tower was swaying rather violently in the fierce winds.

Kaaterskill Falls

If you want a lovely drive through the Catskills, the drive to Kaaterskill Falls would put a smile on any petrolhead. Make sure to take a pitstop at Circle W market, a small town market with a good local breakfast before you embark on another calorie-killing hike. Following a series of small waterfalls, the trek to Kaaterskill Falls is less intensive than Overlook Mountain, but in many ways a very different hike.

This photograph of the bridge near the start of the hike was taken from some smaller falls that make for a delightful start.

Kaaterskill Falls

At the base of the falls is an icy pool that I'm sure is a popular swim spot in the summer.


When reminiscing back on my Woodstock caper, it always feels like a dream. As if you entered the cartoon portion of Mary Poppins for the weekend. Woodstock isn't Turks & Caicos, it's the getaway you need to if you live in a busy city and want to roadtrip for the weekend. Winter is truly the time to go. And even though most places exude character during the holidays and all of them vying for you to visit them, I still would recommend making Woodstock a must on your list.



  • Zen mountain monastery

  • Woodstock Waterfall Park

  • Karma Triyana Dharmachakra

  • Opus 40

  • Sussin Family Christmas Light Show

  • Saugerties Lighthouse (Saugerties)

  • Rondout Lighthouse (Kingston)

  • Esopus Meadow Lighthouse (South Kingston)



  • Candlestock

  • The Golden Notebook

  • Mower's Flea Market

  • Three Turtle Doves

  • Shop Little House

  • Circle W Market (Before Kaatersville Falls Hike)

I got a sad face and a dress shirt emoji from Grammarly writing this article.

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