Woodstock’s Most-Instagrammed Places

“A decade later, the mystique lingers; the name still draws. Even now, superannuated hippies and flower children, Rolfers, rockers and runaways, bikers, down‐and‐out “skidders,” artists, curiosityseekers and day‐trippers still find some need to make their way to the Ulster County, N.Y., village and art colony that gave its name to a generation.”

Ralph Blumenthal from the NY Times wrote that in 1979, and with just a few tweaks, it could totally apply today. Woodstock has a magnetic pull that originated far before the festival, or even before the Byrdcliffe Artists Colony was a thing in the 1900s; it’s Overlook Mountain, the surrounding Catskills, the swimming holes and trails through the woods that make the whole place seem a little magical. Today, some of that magic gets captured with Instagram pictures; the data we’re sharing in this post is a huge indication of how people are enjoying themselves.

Within a year or two, we totally expect The Lodge (which sponsored this post) to join the other locations on this list. The property has new owners and management, and is host to a restaurant, bar and hotel with six acres of cabins walking distance from the village. We anticipate lots of pictures of tiny houses in the woods and live music. Don’t miss a huge night of jazz on October 30, when they’ll have Jane Bunnett and Maqueque performing at 7 p.m.

Here’s their recent appearance on NPR’s Tiny Desk series:

(About the list below: We’re a creative and strategic agency (branding, marketing & websites) that deals in lots of social media data for our clients. We data-mined a year’s worth of Instagram posts across the region to see which locations are geo-tagged the most in photos: it’s an indication of lots of economic activity, being aesthetically pleasing, and being a place that people are proud to broadcast.)

1. Overlook Mountain

Photo by @davidrosenfeld
Photo by @davidrosenfeld

Overlook Mountain, and the Mountain House ruins and fire tower that sit atop it, was #24 on our list of the Hudson Valley’s Most-Instagrammed Places. A strenuous 2.5 mile hike goes almost straight uphill, where you get to the ruins of the old Overlook Mountain House. According to Atlas Obscura, it was part of the insane movement of the 1800s to build luxury hotels on top of inaccessible mountains. It burned down twice before being partially rebuilt in the 1920s and 30s with concrete, which is what visitors see today. A little beyond the ruin porn is Overlook’s summit, where there’s a fire tower that has views of the Hudson River, Ashokan Reservoir and surrounding mountains. Between the hike itself, the easily accessed hotel ruins and the views from the fire tower, this is one of the most picturesque destinations in the region.

Over 1100 photos were geo-tagged here.

2. Bearsville Theater Woodstock, NY

Photo by @jornswart
Photo by @jornswart

The Bearsville Theater made it on our list of the Hudson Valley’s 51 Most-Instagrammed Places at #46. Seeing Gene Ween (aka “Aaron Freeman”) Do Billy Joel here in 2015 was one of the highlights of our lives. Over 5oo photos were taken here.

3. Levon Helm Studios

Photo by @missmargoprice
Photo by @missmargoprice

Levon Helm Studios was built by The Band member of the same name in 1976, and is affectionately known as “The Barn.” It was the home of the legendary Midnight Ramble series of shows, which we covered a bit in this blog post we recently made for The Lodge, and many artists and musicians record albums there.  Since Helm’s death in 2012, The Barn’s management company has vowed to “keep it goin” in his memory by continuing to put on intimate shows that delight travelers and people both from the nearby community alike.

Over 260 photos were taken here over the last year.

4. Garden Cafe at Woodstock

Photo by @dan_hoye
Photo by @dan_hoye

The Garden Cafe has been providing vegan meals, juices, and treats to both Woodstock natives and its many visitors since 2007. It’s not just food pictures here (although they look delicious even to non-vegans like us); the cafe is located right in the center of town, so there are lots of shots of the Village Green’s goings-on, and there’s also an idyllic garden area for dining on nice days.

Over 200 photos were taken here last year.

5. Big Deep

Photo by @ohhellojoe

If you’re within 20 minutes of Woodstock and it’s a hot one, the Big Deep is probably your best bet for legal swimming hole action. You can find it on Google Maps, there’s free parking, and people are pretty respectful of keeping the area clean and quiet. Wander along the water and maybe you’ll even find a more secluded spot to take a dip. This piece on the Big Deep in the NY Times from 2013 was pretty cool.

180 photos were taken here.

6. Shindig

Photo by @rgiuliani98
Photo by @rgiuliani98

Located right in town, Shindig is food porn central. Seriously, look at all the photos taken there. Locally sourced comfort food with a cozy interior… and those burgers.

160 photos were taken here.

7. Karma Triyana Dharmachakra Retreat Center

Photo by @donicaida
Photo by @donicaida

This is known to many as “that Buddhist monastery near the Overlook parking lot.” It doesn’t look super inviting to new visitors, but ACTUALLY, they have open hours from 2 to 6 p.m. on weekdays, and lots of open hours on weekends too. Guided tours are available on Saturdays and Sundays at 1 p.m. So if you’re visiting Overlook anyway, check it out!

160 photos were taken here.

8. Byrdcliffe Colony

Photo by @ngwirtz
Photo by @ngwirtz

Maybe the Woodstock Festival put the name “Woodstock” in the national consciousness as an artistic, musical place, but 67 years before that, the Byrdcliffe Colony really got that started. It is either the oldest or second-oldest Arts and Crafts Colony in America, and was created as a counterbalance to the Industrial Revolution’s commoditization of human labor as an experiment in utopian living. Keep Byrdcliffe in mind when we’re all replaced by robots in twenty years.

Almost 160 photos were taken here.

9. Cucina Woodstock NY

Photo by @canvasjune

The Cafe at Woodstock and Shindig are great for casual fare for a lazy day in the village; Cucina is more of a destination for fine dining at night. They’ve been written about in places like Vogue, Fodors, and The Guardian. It’s the sister location to Market St. in Rhinebeck.

Over 150 photos were taken here.

10. Oriole9

There has never been a sadness that can’t be cured by breakfast food.” Oriole9 is where Ron Swanson would eat if he were a Woodstock weekender: bacon, eggs, and breakfast all day long.

About 120 photos were taken here.

11. Catskill Mountain Pizza Company

Design Sponge endorsed Catskill Mountain Pizza Company as the best classic slice in Ulster County.

110 photos were taken here.

12. Sunfrost Farms

1/3 smoothie/juice bar, 1/3 diner, and 1/3 organic market, Sunfrost is the perfect place to stop off for a quick meal and snacks before you go hiking at Overlook or Comeau.

Almost 110 pictures were taken here.

13. Hotel Dylan

Photo by @thescout
Photo by @thescout

Woodstock can’t escape the name Dylan: Bob Dylan helped put Woodstock on the map, and since 2014, the Hotel Dylan has been giving travelers a “bohemian-chic” place to stay. The design is a mix of West Elm and vintage Ulster County finds, and each room has a personalized collection of vintage records in it.

Over 100 photos were taken here.

14. The Center for Photography at Woodstock

Photo by @hernease
Photo by @hernease

The Center for Photography is housed in the same building on Tinker Street that was once the Espresso Cafe and Tinker Street Cafe; where Bob Dylan would get too drunk to drive and stay in a room upstairs where he wrote two albums, and artists ranging from Joan Baez, Living Color, the B-52s and the Psychedelic Furs could also be found at times. The Center for Photography was established in 1977, and at some point, they took over the whole building; today, instead of hosting great music, the building is home to world-renowned, provocative photography. Blouin Artinfo named CPW one of the top 20 photography artist residencies in the country, and recent exhibitions like The Space Between: Redefining Public and Personal in Smartphone Photography and Can I Touch It? received national attention.

About 100 Instagram photos were geo-tagged here.

15. Comeau Trail

Photo by @takeshimurata
Photo by @takeshimurata

Want to hike in Woodstock, but don’t want to drive up a giant mountain, and then walk two miles straight up hill? Comeau is for you.

Over 90 photos were geo-tagged here.

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