Hiking Tips

Pro tip: Due to overcrowding and unsafe road and parking conditions (yay, hiking is so popular!), do NOT park on 23a, you will be ticketed and towed. Similarly, they are actively managing some trailheads more than others (most notably, along 23a, and at Platte Clove), but at any trailhead, I'd advise that you only park where the signs say it's ok, or you risk being ticketed and towed. 

Pro tip: To access any of the trailheads along the 23a no parking zones, use the Kaaterskill Trolley Co.! You can purchase a single ride ticket, or a day pass here.

Some of our favorite local hikes (aside from the obvious around the Kaaterskill Falls trailheads)

Under 5 miles:

Huckleberry Rail Trail (nature trails in town, walking distance from the house. the closest access point to the trail is in the Rip Van Winkle Park, by the playground)

Mountain Top Arboretum

Huckleberry Point - 4.5 miles, stunning view

Dibble's Quarry - the link is for the Pecoy Notch trail, but if you just go to Dibble's Quarry it's about 45 minutes each way, and it's a favorite spot to sit and watch the world, stunning views.

Diamond Notch Falls

Over 5 miles:

Indian Head Mountain - this route along Jimmy Dolan Notch clocks in at just under 5 miles, but you could combine it with Twin for something longer

Twin Mountain - again, you could combine with Indian Head, or Sugarloaf for something longer

Blackhead and Black Dome Mountain (and throw in Thomas Cole if you're feeling extra ambitious)

Windham High Peak

Hunter Mountain via Becker Hollow (technically this one is under 5 miles but it's aggressively uphill, so I'm putting it into the over 5 miles category!)