Sugarloaf Hill: Family-Friendly Hike in Garrison

Please welcome back our contributors: Brian PJ Cronin, editor of Hudson Valley Parent magazine and local writer extraordinaire, shares his writing talents in focusing on family-friendly hikes for our Hiking Series. The beautiful photography is by Kristen Cronin, local do-gooder and co-founder of For Goodness Bake. Enjoy!



Today’s hike takes us to Sugarloaf Hill in Garrison. Not to be confused with Sugarloaf Mountain in Cold Spring or the Sugarloaf Mountain ski resort in Maine or the Hudson Valley town of Sugarloaf over in Orange County or the approximately 14,000 other things in the Northeast named “Sugarloaf.” It’s a bit of a common name. Until the late 19th century, before granulated sugar became a thing, refined sugar was processed via conical molds. Once the process was done, the sugar came out of the mold in a tall, mountainous shape, called a sugarloaf. And since early Colonial settlers were too busy trying not to die of starvation and/or dysentery to be creative, they pretty much named every other mountain they saw “Sugarloaf.” So when your kids ask what a sugarloaf is, now you know what to tell them! You can leave out the dysentery part, though.

The parking lot and trailhead are across from the Garrison Institute on Route 9D.
  1. From the parking lot, backtrack the way you drove up and hang a left. Keep following the dirt road as it heads towards the hills and then bears right at another gate. You’ll start to notice red trail markers, which are the markers you’ll be following all the way to the top.
  2. Take a left into a big, beautiful meadow of tall grass and wildflowers. From here the trail is usually mowed into the grass. As you begin to ascend through the meadow, look back and you’ll get a fantastic view of West Point. Keep in mind though, as you’re all getting your Andrew Wyeth vibes on, that if you’re hiking this trail between May and July that you’re basically walking through tick-alapooza. So stick to the mowed parts, use a good tick repellent from the knees down, and do thorough tick checks on the whole family when you get home. (I should add that in the five or so times we’ve done this hike we’ve never found a tick on us, but better safe than sorry.)

  3. Partway through the meadow, the trail splits. Head straight, into the woods, and you’ll come across a wooden gazebo. Turn right, into the woods, for a small shortcut. Both paths shortly meet up again, so take either one.
  4. After crossing a small brook, the trail begins to wind up the hill. Keep an eye out for those red trail markers. There’s plenty of unmarked trails that branch off and lead to private property. On your way up, look for a large climbing boulder, a cairn atop a stone pillar, and a frog pond.
  5. Shortly after the pond you’ll come to a junction. The blue trail begins here and continues straight ahead. There’s another wooden gazebo just up ahead, if you’ve got a bit of time and want to check it out. Otherwise, hang a right to follow the red trail as it ascends. This is the only steep part of the hike, so littler hikers may need a hand here. Fortunately, the ascent is short and you’re almost to the top.
  6. In a few minutes you’ll top out at the ridge. Keep following the trail along the ridge until you reach the end point, with scenic views facing south on the Hudson River. Look around a bit and you’ll find a very rare sight for the Hudson Valley - wild cacti growing near the rocks. Yes, cacti can grow this far north, but the conditions have to be just right. And Sugarloaf Hill is one of those very special places in the Valley that’s got just the right mixture of rockiness, access to open sunlight, and ample drainage within the soil to make that happen.
  7. Backtrack down the hill to return to the parking lot. And check for ticks!
Round-trip distance: 3.1 miles

Where to park: To get to the parking lot, look for the stone gate across from the Garrison Institute on Route 9D. Above the gate, you’ll see a brown DEC sign with yellow letters that reads “Castle Rock Unique Area.” The gate says “Wing & Wing” on it. Bear left on the dirt road, and follow the signs to the lot.

What to pack for the kids:
  • Snacks and water
  • First aid kit
  • Sunscreen and hat (You’ll only need these for the beginning; once you get past the field the rest of the hike is pretty shaded.)
  • Tick repellent
  • Tick key or tweezers
  • Map (See the “East Hudson Trails” map #101 of the New York-New Jersey Trail Conference Series, which is sold at Mountain Tops.)