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Western Highlands

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Beach Rock 
Diamond Ledge 
Grizzly Cliff 
Mattatuck State Forest 
Mile of Ledges 
Orenaug Park 
St. John's Ledges 
Whitestone Cliff 
Rest Day:
Nearby Mountain Bike Rides

Overlook Spur Trail (Red)
A sensational panorama after a hefty climb up Overlook Mountain. Near Woodstock, New York
Cortina Valley to Palenville
A grueling one way ride with some tough terrain, but very rewarding downhill with incredible views! Near Tannersville village, New York
Overlook Turnpike Primitive Bicycle Corridor
Mix of technical singletrack & doubletrack. Near Manorville, New York
Jockey Hill Loop
Counterclockwise loop hitting some of the old classics of Jockey Hill. Near Kingston, New York
Jockey Hill - Wood Rd
An access road for the amazing singletrack littered throughout this part of Bluestone Wild Forest. Near Kingston, New York
A short bear of a climb leading up from Wood Rd to Wintergreen Loop. Near Kingston, New York
From MP's sister site: MTB Project

Western Highlands Rock Climbing 

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Location: 41.9914, -73.4219 View Map  Incorrect?
Page Views: 48,898
Administrators: Morgan Patterson, Kristine Hoffman (sitewide)
Submitted By: Ladd on Dec 10, 2007
You & This Area
Best climbs for YOU in this area
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Kris working the over hanging section near the top...


Climbing in Northwestern CT is not as varied or bountiful as other parts of the state but none the less there are some great areas to grab your rope and get out for some pulling. This region is remarkably more hilly, containing CT's highest spot, the side of a hill that has a summit just over the border into Massachusetts.

Getting There 

There is a network of roads throughout the region although there is no main thruway.

Climbing Season

Weather station 4.1 miles from here

88 Total Climbing Routes

['4 Stars',0],['3 Stars',26],['2 Stars',43],['1 Star',13],['Bomb',0]

Classic Climbing Routes in Western Highlands

Mountain Project's determination of the classic, most popular, highest rated climbing routes for Western Highlands:
Try   5.2 3 8 II 8 D 2c     Trad, TR, 1 pitch, 25'   St. John's Ledges : Lower Ledges
Wilderness Crack   5.3 3+ 10 III 9 VD 3a     Trad, TR, 1 pitch, 30'   St. John's Ledges : Lower Ledges
Green Grizzly   5.6 4c 14 V 12 S 4b     Trad, 2 pitches, 230'   Grizzly Cliff
Try or Fly   5.7 5a 15 V+ 13 MVS 4b     Trad, TR, 1 pitch, 35'   St. John's Ledges : Lower Ledges
Dreadlock   5.8 5b 16 VI- 15 HVS 4c     Trad, TR   Whitestone Cliff : Right Side
Trail Magic    5.8+ 5b 16 VI- 15 HVS 4c     Trad, 1 pitch, 100'   St. John's Ledges : Upper Ledges
First Timer   5.9- 5c 17 VI 16 HVS 4c     Trad, TR, 1 pitch, 30'   St. John's Ledges : Lower Ledges
Structures   5.9 5c 17 VI 17 HVS 5a     Trad, TR   Whitestone Cliff : Right Side
Nectar of the Gods   5.9+ 5c 17 VI 17 E1 5a     Trad, TR, 1 pitch, 60'   Whitestone Cliff : The Slab
Withywindle Wall   5.10a 6a 18 VI+ 18 E1 5a     Trad, TR, 1 pitch, 40'   Diamond Ledge
Crocodile Tears   5.10a 6a 18 VI+ 18 E1 5a PG13     Trad, TR, 1 pitch, 45'   Orenaug Park
The Graduate   5.10- 6a 18 VI+ 18 E1 5a     TR, 1 pitch, 30'   St. John's Ledges : Lower Ledges
Browse More Rock Climbing Classics in Western Highlands

Featured Route For Western Highlands
Rock Climbing Photo: Dreadlock . 5.8. Just lead this today, very nice, ...

Dreadlock 5.8 5b 16 VI- 15 HVS 4c  CT : Western Highlands : ... : Right Side
Climb low angle face and crack until pulling through overhang at top...[more]   Browse More Classics in CT

Comments on Western Highlands Add Comment
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Apr 16, 2011
I am originally from North Canaan, CT but didn't get into climbing until I left for UVM. Have been back and climbed since. The NW Corner has a ton of possibility. Tons and tons of boulders, just need to know where to look. Many quality crags as well, just needs to be some dedication, time, and effort into developing, documenting, and gaining access..I hope to get to be a part of this one day.

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