The Blue Hills Reservation, which is located south of Boston along Route 128, is a vast area of steep hills, woodlands, rivers, and ponds. And while Houghton's Pond is wildly popular in the summer with its beach and huge parking area, there is another body of water nearby (Hillside Pond) that is almost completely unknown. Part of the reason that Hillside Pond is quiet and lesser-known is the fact that there is no real parking area near it, while another reason is because only minor trails lead to the pond. But it is a beautiful spot, with Tucker Hill forming a peaceful backdrop, giving it a tucked-in feel, and deep woods surrounding it that make the pond seem much more remote than it actually is. A narrow and rather rough trail goes around the pond, while a series of slightly wider trails meander nearby.
One easy way to get to Hillside Pond is to park at the Houghton's Pond parking lot, walking along the road east for about five or ten minutes to the Skyline Trail (blue blazes) where you take a right, then follow the blue blazes for a few minutes, taking a left on the green dot trail. From there, follow the green dot for maybe 10-15 minutes to the intersection marked #2112, at which point you can take a left down to the road, then cross the road, continuing on the trail for a few more minutes until you come near the east side of Hillside Pond. From there it's a quick scamper over to the pond.