Rattlesnake Mountain, Casco
You might see an interesting cross-section of humanity if you climb this very popular little mountain on a summery weekend day. The day I visited, in August, 2017, two kids dressed as knight errants were hiking to the peak. When I crossed paths with them, they gallantly retreated to the side of the trail, swords held in front of them, but they were stone silent behind their visors, not saying a word in greeting.
Anyway, I am sure that is a little out of the norm. There are at least three ways to summit this mountain — the most popular trail by far being the Bri-Mar Trail, off Webbs Mills Road (Route 85), on which you cannot bring dogs. There are two other ways I saw hikers summiting — one trailhead starts on the other side of this little 1,035-foot mountain, from Route 121 or Meadow Road, and another begins from Coffee Pond Road. A local told me there is yet a fourth trailhead, but I got too exhausted to find it! At least one other trailhead was shut off in the recent past by neighbors concerned about people’s mistreatment of the area.
The Bri-Mar trail is really easy to follow, although it is not consistently blazed (there are a few spray-painted arrows on rocks). At one point it branches in two, but these legs join up very quickly again. It climbs steeply. (By the way, when I tried to hike here last winter, the small parking area — which fills up fast on a nice day — was not plowed and it was not safe to park on the side of the road.)
After you hike about .8 miles on the Bri-Mar Trail, you reach the first ledge and view. From here, if you continue to the other lookout, about .5 miles along the path (and down a bit), you will see other trails coming in from the right (I counted three). Two are tagged with orange flags. (The one in the middle goes nowhere.) These trails form a loop and eventually come out on Coffee Pond Road. But be careful, there are other multi-use trails that intersect with the main trails. I don’t think people other than locals really need to use these trails, since there are two perfectly fine ways to summit.
So the other way to summit this mountain is off Route 121, where you can park at a gate and walk the gravel road about 1.4 miles to the footpath. The trail heads off to your left, and is blazed. Snowmobile trails continue on here. The footpath climbs steeply to one of the two viewpoints on this mountain. I think this one might be the nicer of the two. I saw locals walking their dogs on this trail, and they told me it’s okay to walk dogs on this side of the mountain.
Directions: If you coming from the rough on Route 302, take a right on Route 85 in Raymond, also called Webbs Mills Road. Go about 7 miles and you will see the trailhead and parking area on your left. (It is about .9 miles from the junction with Route 11. The trailhead off Route 121 is about 2.4 miles from the intersection with Route 11. It is a small area in front of a gate. No motorized vehicles are allowed past the gate. The trailhead off Coffee Pond Road is also gated, and there were two cars parked at the little roadside pull-off when I visited this mountain.