Skinner State Park encompasses Mt. Holyoke, Mt. Hitchcock, Seven Sisters, and Bare Mountain.
My favorite hike for Mount Holyoke is to hike from one end of the park to the other end as a point-to-point hike. This is best done with two cars. One car parks near the Main Entrance of Mount Holyoke and the other one parks at the Notch Visitor center on route 116. I like starting at the Notch visitor center. The parking area does have bathrooms and such if needed. Then you cross 116 to start hiking the M&M trail to the summit of Bare mountain (1010ft). This is a bit of a steep incline up but about 1mile in you reach awesome views. The summit of Bare Mountain is really nice.
Then you continue on the M&M trail going over Mt. Hitchcock (1005ft). After Mount Hitchcock, you will start on the Seven Sisters peaks which are seven small peaks for about 5-mile distance. Lastly, you hit Mount Holyoke which offers the best views (in my opinion) of the entire hike. Spend some time enjoying the summit house and head down to the car parking lot. The total distance of the hike is about 10miles.
This is a very dog-friendly hike and we always see lots of pups on this hike.