I grew up in GB but didn’t become a climber until well after I left. I know there is some good bouldering, but how about roped climbing? I recall a freezing cold 7th grade field trip so there’s at least one route yeah?? Anyways, I’m heading home next week for the first time in several years and it’d be fun to get out. I’m an adept trad and sport climber but not really a boulderer. Interested in any beta you have to share!
There is excellent roped climbing in Great Barrington, though not nearly as popular as the bouldering and likely not to be in great condition at this time of year. The main crag is called Reservoir Rock and is located directly up the hill above the main bouldering area. It is all trad or top rope, mostly the latter ( long story why). Basically keep following trails to the left and uphill ( final bit might be overgrown) until you reach the cliff ( there is a short outcrop(with a couple of climbs) below the main cliff that the trail skims to the right). Where the trail meets the cliff you are at an impressive face roughly 90' tall, with a thin crack line on it's left--this is Endeavor to Persevere--10c--the crag classic but not an easy lead. Just left the wide flake crack is Big--7/8. In addition to Endeavor there are 7 top ropes right of Big in the 10/11 range. Further left the cliff gets shorter with plenty of top-ropes. The left-most buttress has some shorter, lower angle routes in the 8/9 range. The trail/ scramble to the top is just left of this. There is more rock right of Endeavor but.harder to access and overall not as good quality, as well as other cliffs in the region that are much harder to access. An exception is Bung Hill just as you are coming into town from the north ( above the intersection of Route 7 and Route 23--I think) with shorter outcrops near the road but you have to be careful to avoid private property here. The obvious cliffs on Monument Mountain a bit further north are off-limits ( and mostly dangerously loose anyway).
I want to follow up my previous response with some additional information. While not in Great Barrington, but not far away, you might want to visit Hanging Mountain in Sandisfield,MA--about a 20 minute drive, I'm guessing. Hanging is the tallest cliff in the State ( though most routes are single pitch) and is located directly above Route 8 just a few miles north of the Connecticut border--reached from GB via Route 57 east. Most of the cliff was purchased a few years ago jointly by the Western Mass Climbers Coalition and the Ragged Mountain Foundation and has a good mix of sport and trad routes from roughly 5.7 --up. It has a dedicated parking area and a short approach, so easier to locate and get to than Reservoir Rocks. Directions to both Hanging and Reservoir are on the WMCC website (climbgneiss.org), including a free downloadable guide to HM.
Even if you aren't climbing this trip, it will be worth bringing your approach shoes and walking in to check out the areas. A reconnaissance of the Resevoir area now, will save time on a later trip and the drive and walk into Hanging Mountain is a worthwhile way to spend a 1/2 day--if for nothing else than to admire the impressive trail work there!!!! Both are good ways to work off the T-day excesses!!!!