Houghton's Pond is one of the most developed parts of the reservation. The pond itself is a favorite swimming place, and sports a good-sized parking lot, visitors' center, bath house, pavilion, "nature" boardwalk and playground. The pond is also surrounded by picnic areas. Families come and spend the day. (On summer weekends, its popularity makes parking very difficult.) A path winds around the pond, touching the shore in places, and connecting the picnic areas. It's a nice though very civilized walk of about half-a-mile.
But the Pond is also a jumping-off place for other trails, including Dark Hollow Loop, and other, connecting, trails. Going left along the trail above the pond shore, Houghton's Pond Loop curves to the right to follow the pond edge, while the road to Dark Hollow Loop diverges to the left.
I visited on a weekday and a school day, as I like a bit of solitude. The Pond proper had only a handful of visitors, and I met fewer than a dozen other hikers over two or three hours of walking. This is a somewhat busier trail than the quiet Braintree Pass Path. But this is one I will come back to.
A good topographic map of the reservation and its trails is available at the ranger station a minute away at 695 Hillside Street in Milton, or at the Blue Hills Trailside Museum on Canton Street, Milton for $3. If you're too cheap, or you forget to bring it with you (as I did), there are trail directions at the bottom of this post.
"Houghton's Pond Loop 0.75 miles (30 minutes) easy (yellow dots)
A short scenic hike around the popular Houghton's Pond. This walk is very picturesque during fall foliage season. Walk from the bulletin board at the main parking area and head down to the pond; circle the pond using the paths and roadway. Yellow marks on trees guide the way." --Ranger Tom's Suggested Hikes
"Dark Hollow Loop 2 miles (1.5 hours) easy, or moderate with the Tucker Hill addition
This mostly-level forested loop trail takes you through oak-pine woodlands. For the more adventurous, a side trip up Tucker Hill provides find views of Houghton's Pond and surrounding areas. From the Houghton's Pond bulletin board, walk toward the bathhouse. Follow the green dots which begin past the bathhouse and loop around the base of Tucker Hill. To climb Tucker Hill, follow the green dots to the Skyline Trail (blazed in blue) and head uphill to the summit of Tucker Hill." --Ranger Tom's Suggested Hikes
Houghton's Pond is very developed.
Leaving the paved path to begin Dark Hollow Loop proper.
Not sure; some kind of aster? I'll put it up on iNaturalist.
The lower part of this chestnut is still alive,
even though chestnut blight has invaded the trunk higher up.
Four paths diverged in a wood...
Hay-scented fern, perfuming the way, is often smelled before it is seen.
I interrupted this snake sun-bathing. He got under cover hurriedly.
I have no idea why this hollow is here; but then again I never know what causes them.
Wreath goldenrod (Solidago caesia) would make a decorative headband.
Long, rocky slope of Tucker Hill is thick with fallen trees.
Probably mayapple (Podophyllum peltatum).
Another way to access Dark Hollow Loop--but with almost no parking--is from Chickatawbut Road.
Huckleberry in autumn trim.
Stump sprouting is the way chestnut survives repeated attacks of chestnut blight: the fungus kills the trunk but the roots send up another--and then another and another and another--each one killed in turn when it grows large enough to develop cracks in the bark that allow the fungus to invade.
The path atop the hill, which joins the Skyline Trail. It is a bit confused on the map,
but just begin heading uphill at around intersection 2072.
The top of Tucker Hill.
View from atop Tucker Hill.
Pineweed (Hypericum gentianoides). does well on dry, sunny hilltops.
Scrub oaks in the dry ground near the top of Tucker Hill.
Sweet goldenrod (Solidago odora).
The beech most likely being parasitized.
Rattlesnake root (Nabalus) of some kind.
Houghton Pond Loop
One or another of several species of Pondhawk (Sympetrum) dragonfly.
Looking at the beach from across the pond.
New York aster (Aster novi-belgii), maybe.
Virginia creeper in fall trim.
Directions for doing the Dark Hollow loop: Park in the lot beside Houghton Pond off Hillside Street, Milton. Walk eastward along the trail by the pond. Near the end of the pond, the green dot trail that diverges from the trail that circles the pond. The trail turns north, and goes uphill on pavement. Intersection 2070 is the beginning and end of the loop. Going to the right on the dirt path (counterclockwise around the loop), go left at intersection 2075, left (L) at 2096, straight north at 2094, past the Skyline Trail (blue rectangles), L at 2112, L at the forks (the second is at the road), straight (south-southwest) at 2081, R at the fork, past the Skyline at about 2072, and south to meet the trail stem back at 2070. South on the pavement will bring you quickly back to the pond. If you decide to go to the hilltop (for exercise, a different environment, and a bit of a view) you can follow the Skyline Trail at either point where it crosses the loop, or simply head uphill on one of the trails that crosses the loop near 2072 (as I did). Seriously, get the map when you have a chance.