When we think about the Town of Esopus, NY 5 Hs come to mind: Hikes, History, the Hudson, and Headless Horseman.

We’ve spent a lot of time getting to know Esopus over the years while living and working in Kingston. We recently brought on board to help the Town with some content marketing, by creating blog posts and social media graphics for them on subjects like:

5 Reasons to Move to Esopus Now

Four New York City Commuters and Remote Workers on Why They Live in Esopus, NY

Seven Business Owners Who Love Esopus, NY

15 Outdoor Things You Can Do in Esopus, NY

Three Volunteer Initiatives by Esopus People Who Care

While researching these articles, we also looked up Esopus’ Most-Instagrammed Places for fun. We pulled down a year’s worth of Instagram posts taken within the town, and did some data magic to figure out which locations got geo-tagged the most by people posting pictures to Instagram. The result is a snapshot of what the most popular attractions are in town for both locals, regional tourists, and visitors from far away. You can find some more information about our methodology in our article in Search Engine Journal.

(Note: Posts by businesses themselves or their employees were not counted for this post.)

1. Headless Horseman Hayrides and Haunted Houses

1643 Photos

Photo by @ramalotte666

Headless Horseman Hayrides & Haunted Houses (or Headless Horseman for short) is a big deal not just for drawing people to the Town of Esopus, but for the Hudson Valley and New York State. It was founded in 1992 by Mike and Nancy Jubie. Mike, in his line as a work as an undercover and mounted patrol officer with the Kingston Police Department from 1971 to 1994, had a knack for disguises and horses. As a couple, they also were way into Halloween. In 1992, they bought a 65-acre farm in the hamlet of Ulster Park, off of Route 9W, and have been hosting scary, immersive Halloween events ever since. While most of their photos happen during the season between September and Halloween, they also have a new year-round offering of an Escape Room experience, as well as a kid-friendly Frosty Fest for the Christmas season.

They’ve been written up in everywhere from Mental Floss to Buzzfeed to Vice to Narratively. They’re good, folks.

2. Red Maple Vineyard

1032 Photos

Photo by @c10ike

The pictures speak for themselves; this is a great place to have an idyllic Hudson Valley wedding. But it’s a little more interesting than *just* a beautiful venue. The property is operated by a long-time Westchester catering company called Cornerstone Caterers, and they operate a farm on the premises; as much of the produce for each wedding is sourced right from the farm, and they also are making wine, honey and jam there too. They recently did a collab with Great Life Brewing to brew a special beer with sap from the vineyard’s trees, too.

3. Black Creek Preserve

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Photo by @beast_elise

This is a hike that is easy to get to and delivers the goods quickly. It’s right off of Route 9W, and after a quick 2 mile jaunt over a suspension bridge and along the herring breeding grounds of Black Creek, you get to the money shot: the shores of the Hudson River. There’s a good chance you’ll see some wood frogs, chipmunks and wild turkeys along the way… and a tiny chance you’ll even glimpse a bald eagle.

4. Shaupeneak Ridge

492 Photos

Photo by @imcgrew

Another Scenic Hudson joint, this has nine miles of challenging trails, and since there are several different loop options, you can mix and match over several repeat visits. There’s a lake (which people walk across and fish on when it’s frozen over), there’s a waterfall, grasslands, and some views (although nothing as expansive as at Black Creek), but the coolest thing is that Sojourner Truth actually went through Shaupeneak on her walk to freedom.  A homeschool group called Epic Explorers put together a seven-step geocache trail where you can retrace some of Sojourner’s path.

Hike the Hudson Valley (which we just re-launched) has a great trail guide for Shaupeneak too.

5. Esopus Meadows Preserve

375 Photos

Photo by @rorythebasenji

Like Black Creek Preserve, this is a quick and easy hike, simple to get to, with the payoff of getting to the shores of the Hudson River. The big point of interest is the Esopus Meadows Lighthouse, which actually has its own Instagram location but we lumped it in here. It’s the last remaining wooden lighthouse on the Hudson River. There’s also the Mills Mansion that you can kind of see across the river, as well as this cool sign.

Photo by @macon_fess

6. Marist Brothers Center at Esopus

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Photo by @mackenziee_smith

The Marist Brothers Center is a 120 acre estate that is visited by over 4,000 young Marist-affiliated people annually. In the summer, it’s home to the Mid-Hudson Valley Camps, which serve special needs populations for nine weeks. The grounds have access to the Hudson River, and it’s also home to the Oliver Hazard Payne estate, which was bequeathed to Marist College in 2009 and is used for leadership conferences and college functions.

7. Wood N’ Wheel

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Photo by @kalmonger

They’ve got roller skating, but there’s also laser tag, paintball, outdoor climbing, bungee trampolines and an arcade.

8. Sturgeon Pool

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Photo by @p__eazy

This is the place to go for smallmouth bass.

9. Stonehedge Restaurant

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Photo by @danacoachdigi

They’re open as a sit-down restaurant, but most of the Instagramming here seems to happen at events like weddings or paint and sip nights.

10. Rainbow Drive-In

26 Photos

Photo by @tomebsmith

Also known as the Frozen Rainbow, this is where Esopus gets its non-Stewarts soft-serve ice cream. There’s also a cool sit-down diner inside.

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