New York · Hiking · Near New Windsor

Highlands Trail

Highlands TrailPhoto: daveclausen, CC BY 2.0 (via Flickr)
76.8 mi
one way
13,233 ft
climb
1,607 ft
high point
Point to point
route
Apr–Oct
best months

Highlands Trail is a long, point-to-point hike in New York, about 2 miles from the small community of Dutch Hollow. The route stretches roughly 77 miles, rising from a starting elevation of about 740 feet to a high point of 1,607 feet, with a total elevation gain of about 13,200 feet. It is rated easy, and the trail is not open to horses or bikes. Late spring and early fall are the most comfortable times to go. Typical averages from a nearby weather station in Middletown run to highs around 70°F in May and 73°F in September, while July highs reach about 82°F. That station sits roughly 900 feet lower than the trail's high point, so temperatures on the higher ground run cooler. The Doris Duke Trail lies about 1.3 miles away, and the Allis and Sterling Ridge hikes are each about 3 miles off. Paddlers can find Wawayanda Creek about 6 miles away.

Around this trail

Add any of these when you start a trip
  • Sleep close

    Camp Wabenaki

    Campground

    Campground · 5.4 mi from the trail
  • Eat after

    Rusty Knife Pub

    Pub

    On your way back · 2 mi
  • If it rainsDoug Kerr from Albany, NY, United States, CC BY-SA 2.0 · Wikimedia Commons

    Storm King Art Center

    Museum

    On your way back · 14 mi

    Open-air museum and sculpture park located in Mountainville, New York

Places © OpenStreetMap contributors · Photos: Doug Kerr from Albany, NY, United States, CC BY-SA 2.0 (commons)

More in New Windsor

Local outfitters

Not on Roamze yet. Their page has how to reach them.

  • Best time to go · Apr–Oct

    Best time to visit Highlands Trail

    Best months: April–October. Best months have typical highs of 55–85 °F, lows of 30 °F or warmer (32 °F where the station doesn't record snow), at most one snowy day and no more than 12 wet days.

    1. Jan

      34° / 18°

      8 wet

    2. Feb

      37° / 18°

      7 wet

    3. Mar

      47° / 26°

      8 wet

    4. Apr

      60° / 38°

      9 wet

    5. May

      70° / 48°

      11 wet

    6. Jun

      78° / 57°

      10 wet

    7. Jul

      82° / 62°

      9 wet

    8. Aug

      81° / 60°

      9 wet

    9. Sep

      73° / 53°

      8 wet

    10. Oct

      62° / 43°

      8 wet

    11. Nov

      50° / 33°

      8 wet

    12. Dec

      39° / 24°

      9 wet

    Typical high / low (°F) and days with rain or snow, 1991–2020. Measured at Middletown 2 Nw, NY, 16.4 mi away at 700 ft. The station sits about 900 ft lower than this place, so expect it a little cooler here. This station doesn't record snowfall. Source: NOAA NCEI U.S. Climate Normals 1991–2020.

Keep exploring — more trails worth the drive

AllisPhoto: Zeete, CC BY-SA 4.0 (via Wikimedia Commons)

Allis

~5 min drive

3.73-mile out-and-back trail in New York with 635 ft gain.

Sterling RidgePhoto: Zeete, CC BY-SA 4.0 (via Wikimedia Commons)

Sterling Ridge

~5 min drive

5.83-mile out-and-back trail in New York with 769 ft elevation gain.

Townsend TrailPhoto: rpkelly22, CC BY-SA 2.0 (via Flickr)

Townsend Trail

~6 min drive

2.14-mile point-to-point trail in New York with 777 ft elevation gain

Pine MeadowPhoto: rpkelly22, CC BY-SA 2.0 (via Flickr)

Pine Meadow

~8 min drive

7.49-mile out-and-back trail in New York State Park and Recreation land.

Sterling Valley LoopPhoto: LukeGordon1, CC BY 2.0 (via Flickr)

Sterling Valley Loop

~5 min drive

Sterling Valley Loop is a 4.90-mile out-and-back trail in New York with 805 feet of elevation gain.

Bare Rock TrailPhoto: rpkelly22, CC BY-SA 2.0 (via Flickr)

Bare Rock Trail

~8 min drive

Point-to-point NY trail featuring exposed rock outcrops and scenic vistas.

Long Meadow ExtensionPhoto: rpkelly22, CC BY-SA 2.0 (via Flickr)

Long Meadow Extension

~6 min drive

Gentle 1.90-mile point-to-point meadow walk in New York.

Fire Tower Connector TrailPhoto: History tower, CC BY-SA 3.0 (via Wikimedia Commons)

Fire Tower Connector Trail

~9 min drive

0.47-mile point-to-point trail in New York with 235 ft elevation loss.

HIKE

Wildcat Mountain Trail

~8 min drive

Short point-to-point mountain hike with scenic views near Wildcat Mountain.

Long Meadow ExtnesionPhoto: rpkelly22, CC BY-SA 2.0 (via Flickr)

Long Meadow Extnesion

~6 min drive

0.88-mile out-and-back trail in New York with 267 ft elevation gain.

Map and trail data © OpenStreetMap contributors