Bear is really a subsidiary summit of South Boulder Peak, but with a satisfying summit with terrific views. The standard route starts from the Cragmoor TH, at the west end of Cragmoor Road, and ascents the Cragmoor Connector, North Fork Shanahan and Fern Canyon trails to the true summit of Bear Peak, where there is a benchmark. These trails can be seen on this map, though the Cragmoor TH is not labelled. It is about 2.5 miles with 2500' of elevation gain. There is a Strava segment for this route, but note that Strava can be off by numerous seconds so it's best to post your actual time as well as your Strava track.