Bear Mountain is just about in the center of the large untrailed area of Allegany State Park bordered by Quaker Run on the southwest, Route 280 on the northwest, Bay State Road on the northeast, and ASP1 on the southeast. There is a USGS Benchmark on the summit of Bear and a USGS reference mark just a few yards nearby.
There is an unofficial trail leading to the summit of Bear from the parking area that is on the north side of the bridge over a creek on Bay State road (about 4 miles from ASP 1). The trail climbs 850 feet over its 1.5 mile length, and is the shortest distance approach to the summit of bear, although because of the elevation gain, it may not be the shortest in time. The trail is partially marked with mostly blue flagging, and some orange flagging. Parts of the trail are blocked by blow down requiring short detours. Parts of the trail are difficult to discern because of missing flagging or obvious trail on the ground.
An alternative approach to the summit of Bear is mostly a 4.5 mile bushwhack from the overlook parking area on ASP 1. The first mile is an orange flagged (and some red blazes on trees) horse trail that is very obvious on the ground in addition to the flagging and blazes. The remainder of the bushwhack is a short climb up to a ridge that is then followed to the summit of bear.
We recently went to the summit of Bear via the bushwhack from the overlook parking area on ASP 1, then hiked about 1/3 mile down the northeast side of Bear until we found the blue flagged trail and then followed it back to Bay State Road. Shuttling cars between the two parking areas would avoid the long hike back on Bay State Road we had to take as depicted on the maps below.
Walk 300 feet west southwest on ASP 1 to the start of the first curve. Enter the woods and look for the orange trail markers.Park at the overlook on ASP1 (south of Bay State Road)
Follow the orange trail (used for horseback riding.) It is marked with red blazes on trees in some sections.
At .25 miles from the overlook parking lot the trail begins a steady 130 foot decent for the next .40 miles. Then the trail levels out for the next .30 miles.
At .90 miles from the parking lot the marked trail turns north and proceeds in a col between two ridges. This is the point where you want to start heading west up the hill to your left. Waypoint “Bear 01” at 42.04844, 78.79249 (NAD27).
From this point to the Bear USGS Survey Marker there are no trails. Basically, you want to head west northwest for approximately 2.60 miles, staying on the ridge that will take you to Bear Mountain.
You will climb amount 100 feet over the next .20 miles. Then the track makes a slow 50-foot climb over the next .40 miles. You are now 1.5 miles from the parking lot and headed west. Over the next .50 miles you’ll descend 50 feet then climb back up 50 feet. At this point you will be on a hill with ridges heading north, south, east, and west. You want to turn north and follow the ridge that descends north, and then curves to the northwest.
At 2.70 miles you need to turn west. After another .10 miles you will finish the descent and begin climbing a small hill as you head west. After another .10 miles (at 2.90 miles from the parking lot) you will start a climb up a small hill to the northwest. At 3.25 miles you will be at the base of Bear Mountain. You will head west and ascend 120 feet over the next .25 miles to the peak of Bear Mountain.
You can either return the way you came, or descend the northeast side of Bear Mountain for .30 miles until you cross a trail marked with blue flagging which will take you to the parking lot for that trail that is on the north side of the bridge over a creek on Bay State Road. This trail is marked with blue and sometimes orange flagging, put is sometimes difficult to follow.