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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 Cliffs 
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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 Palenville, New York
Overlook Turnpike Primitive Bicycle Corridor
Mix of technical singletrack & doubletrack. Near Manorville, New York
Jockey Hill - Wood Rd
An access road for the amazing singletrack littered throughout this part of Bluestone Wild Forest. Near Lake Katrine, New York
Pittsfield State Forest
A tour of Pittsfield State Forest including hard climbs, rowdy descents, and a traverse of the Taconic Skyline Trail. Near Lanesborough, Massachusetts
Lower Ridgeline
The main trail that runs along the western ridge with rocks, roots, climbs, and drops. Near West Hartford, Connecticut
From MP's sister site:

Western Highlands Rock Climbing 

Photos:  Recent | Best | Popular
Location: 41.9914, -73.4219 View Map  Incorrect?
Page Views: 35,149
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

127 Total Climbing Routes

['4 Stars',1],['3 Stars',38],['2 Stars',58],['1 Star',16],['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
Romancing the Stone   5.6 4c 14 V 12 S 4b     Trad, TR, 1 pitch, 60'   Whitestone Cliffs : Main Slab
Tree Skirt   5.7 5a 15 V+ 13 MVS 4b R     Trad, TR, 1 pitch, 40'   Whitestone Cliffs : Main Slab
Dreadlock   5.8 5b 16 VI- 15 HVS 4c     Trad, TR   Whitestone Cliffs : 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 Cliffs : Right Side
Nectar of the Gods   5.9+ 5c 17 VI 17 E1 5a     Trad, TR, 1 pitch, 60'   Whitestone Cliffs : Main Slab
Crocodile Tears   5.10a 6a 18 VI+ 18 E1 5a PG13     Trad, TR, 1 pitch, 45'   Orenaug Park
Withywindle Wall   5.10a 6a 18 VI+ 18 E1 5a     Trad, TR, 1 pitch, 40'   Diamond Ledge
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: Fun Classic at Diamond ledge. good for beginner to...

Mountain Laurel 5.7 5a 15 V+ 13 MVS 4b PG13  Connecticut : Western Highlands : Diamond Ledge
fun route that takes a few tries before finding the right foot placement. starting off on the big triangular boulder at the bottom, there are some big jugs leading up to the first lower ledge about 25 feet up. The slopey wall after that is the crux, there is a few ways you can do it, some climb straight left from the ledge then go up, others will balance their feet on the slopey wall using a few tiny crimpers to get you to the next jug....[more]   Browse More Classics in Connecticut

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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