Overlook Mountain Hike near Woodstock, NY

A 90 minute drive from NYC will bring you to the Catskills, a land of fresh heirloom tomatoes from roadside markets, clear night skies filled with stars, ice cold swimming holes and views like this:



This video was taken at a scenic overlook point on Overlook Mountain, reached via a steady uphill climb along a gravel road- about a 3-hour round trip journey. The trail head is easy to find - from the center of Woodstock, drive up Meads Mountain Road and it is across from the Tibetan Buddhist monastery of Karma Triyana Dharmachakra.  The entrance sign cautions to be wary of rattlesnakes (seriously?) ... fortunately we didn't see any.

At the top of the hike are the remains of the Overlook Mountain House, a prestigious old Catskills resort from 1820-1920. According to the www, in the 1800's it was allegedly "fashionable to take a vacation to the Catksills instead of Europe."

We stopped by the North/South Lake for a picnic lunch - great setting with boat & canoe rentals - though the beach was a bit crowded so we left in search of a swimming hole.

There are several great swimming holes around Woodstock - get ready for ice cold water. This swimming hole with a rock to jump off of is relatively easy to find - continue along 23A past Kaaterskill Falls and park in the small gravel lot on the right. Another one just outside of downtown Woodstock has a rope swing - turn right into the gravel parking road across from Gallo's nursery on Route 212.

Don't leave the Catskills without stopping by Vinnie's roadside farm stand on Route 32 to get amazing heirloom tomatoes to bring back to the city.

Catskill trees. Lots of 'em.

Gigantic Pool in Red Hook

So there's a gigantic pool in Red Hook with hardly anyone in it. And there are only two weekends left in the summer to take advantage of it. Get there! Bike (6 miles from the West Village via BK bridge), take the NY Water Taxi or hop on the F train and get off at Smith - 9th street.

I'm not sure that I've ever been in a pool this big, at 330 x 130 ft ... of course it wasn't this empty, but it didn't have that "taking a bath with 500 people" feeling you get from other NY public pools.

There were actually even a few plastic lounge chairs that freed up towards the end of the session. Make sure to bring a lock and flip flops. Trust me - you do not want to walk around in that locker room without them.

Afterward, we couldn't resist a repeat of The Lobster Pound and Steve's Authentic Key Lime Pie. The Swingle is just too good to pass up. Another option is the Red Hook Ball Fields across the street from the pool for authentic Latin American food - vendors line the fields under tents selling empanadas and tacos on Saturdays. Delicioso.