Kennard, Skyline, and Lost Pond Loops (Kennard Park/Lost Pond Sanctuary/Skyline Park/Lost Pond Reservation/Kennard Conservation Area)
Hike Type: o-o-o Loop
Distance: 3.20 miles
Elevation: 217 feet
My Time: 1 hour, 11 minutes
Book Time: 1 hour, 42 minutes
Parking: Parking for ~10 cars at Kennard Park
Hiking Challenges: 52 Hike Challenge 2026
Hiking Challenges: 52 Hike Challenge 2026
The Hike
I found myself highly unmotivated to go to the Fells after school, or moreso not wanting to sit in an hour's worth of traffic on the drive home after hiking the Fells. I bargained with myself, poked around AllTrails, and found a 3+ mile loop right off of Dudley Road in Newton - sold! It was a chilly afternoon in the low 50s, but nice and sunny with an occasional breeze. I was planning on sticking to the AllTrails route, but just in reverse.
My hike started on a driveway, facing away from Dudley Road, and then reading the abundantly clear signs and turning left onto "public trail." The trail was loosely blazed in skinny red rectangles. I came to a stone wall and an old twin spigot situation, turned to follow the stone wall, and then turned left to cross the stone wall (after crossing paths with a comically wealthy looking woman and her equally-as-wealthy-looking dog. This brought me into DCR's Lost Pond Reservation.
I followed some green arrowed blazes and continued straight/left at the next junction, beginning to circle the Brookline Municipal Transfer Station. I hiked up and around the pretty woods on a trail that was lined with logs but became more obscure near the height of land. I caught occasional "views" to the transfer station.
Continuing along, I stayed on this trail which brought me to Saw Mill Road, which I crossed and continued on a footpath over and then along Saw Mill Brook. I caught up to another woman and her dog, who were busy watching a younger deer scratching it's antlers on a young tree. I would have gotten a photo, but I wanted to keep moving. Fun to see, though!
I followed the woods path, soon crossing the Saw Mill Brook again and entering Skyline Park. I made a loop of the trails here, and was surprised to find a full playground and turf field at the top. There were no views, but plenty of nice space for recreation and picnics. I found some information about the park on brooklinema.gov:
"About the Park
This is Brookline’s newest park, and the first new park added in over 25 years. The park includes a regulation sized, multi-purpose synthetic turf field, a playground with play equipment for all ages, a covered shelter with picnic tables, benches, recreational pathways that connect to Lost Pond Sanctuary, landscaping with new plantings, restored wetlands, a comfort station, and a parking area. Skyline Park is situated on the top and sides of a gently sloping hill, allowing for scenic views of the surrounding area.
Park History
The location is the site of the former town landfill, the Newton Street Landfill, which was capped and the land reclaimed for a public park. Funding for the new park was provided by the Town of Brookline, the Commonwealth of Massachusetts Urban Self-Help Program, and the Brookline Travel Soccer Club. The park was named Skyline Park and was officially opened in 2008."
I thought it seemed like an old landfill!
I backtracked to Saw Mill Road and turned right to hike towards the Transfer Station, which was lined in litter and a unique smell... Thankfully the smell only lasted for a few minutes thanks to the wind. At the gate for the transfer station, I veered right to get back into the woods, eventually landing at a large kiosk for the Lost Pond Sanctuary:
"While much of Brookline and Newton grew and developed during the nineteenth century, with new roads, streetcars, neighborhoods and commercial districts, this area's irregular landscape and relative remoteness from town centers kept it in a natural state. Some portions were used for grazing or farming, but its interspersed wetlands, rocky outcrops and streams made it undesirable for further development. Over time the land came into public ownership, mostly for conservation or recreation purposes. Beginning in 1945, part of the land was used as Brookline's municipal trash site. Between 2004-2008, due to a change in waste management operations and to comply with environmental regulations, Brookline took down the incinerator smokestack, and closed and capped the landfill. This allowed for the development of new recreation areas at Skyline Park and extension of a trail network through these linked natural areas.
Lost Pond: The Lost Pond area includes a pond, streams, marshes, bogs, forested uplands, and meadows. The Pond is certified as a vernal pool. Surrounded by residences, roads and commerical areas, this large natural area and protected water resources provide wildlife habitat for diverse plants and animals. Lost Pond, a "kettle hole" pond, formed around a mass of ice left by glacial activity over 17,000 years ago and is one of the only batural ponds remaining in Brookline.
Peat Bog: Along the northern edge of Lost Pond, a quaking peat bog has developed. Peat bogs, which often occur in deep glacial lakes, are formed by the gradual decomposition of plant material in highly acidic, poorly drained areas. The peat forms a floating mat over the water and provides a base for acid-tolerant vegetation which grows in from the edge of the pond. This wooded wetland is home to salamanders, dragonflies, and other insects and amphibians, as well as white cedar, ferns, poison ivy, and jack-in-the-pulpit.
Forested Upland: The path beyond Lost Pond leads to a forested upland area, an environment in stark contrast to the wetland. Oak trees replace the birches and maples of the low-lying area, and the woods are floored with low-bush blueberry. Visitors can look for: turkeys, owls, harks and other birds; deer, rabbits, skunks, and other mammals; towering hemlock, white pine and shag-bark hickory.
Trail Network: This 135-acre area consists of six adjacent open space properties managed by the Town of Brookline, the City of Newtown and the Commonwealth of Massachusetts. All are open to the public and, except for Skyline Park, are natural areas intended primarily for passive recreation. A network of trails connects all the properties and can be entered from points in Brookline and Newton, as indicated on this map. Together the six properties function as one large cohesive greenspace and highly functioning ecosystem spread across several geopolitical boundaries."
I followed the trail over towards Lost Pond, which had a nice boardwalk that led to a small floating dock. There was a mom and her ~12 year old son rocking the dock to make waves, and she looked embarassed when I landed. The pond was cute! Nothing spectacular, but still nice.
The main trail hit a partially-rotten stretch of boards and as I was thinking of cutting the route short, I realized it was only 4:00pm, so I decided to stick to the plan.
I worked my way towards junction E and the Kennard Conservation Area (after getting slightly off-trail for a minute) and noticed some orienteering course posts. The woods were beautiful and full of pines. The pines did ultimately lead to a slip and fall, but I'll forgive them! There was a bridge over some wetlands leading to junction C, and a more extensive boardwalk bridge at B. On the far side of the wetlands there was a more proper bridge at the site of an old dam, and then there were some Christmas ornaments on a small pine tree. I saw a couple abandoned adironack chairs on the left in a swampy area, and soon I was hiking to junction N and through an open field back to the car!
Horrifically, my Garmin didn't do a good map for me, but this was a solid way to spend a Tuesday afternoon!
Step-by-Step
- Start hike at Kennard Park walking away from Dudley Road.
- At L, turn left.
- At K, turn right.
- At E, turn left.
- At F, turn left.
- At G, continue straight.
- At H, turn right and hike loop around Skyline Park, returning to H.
- At H, turn right.
- At I, turn left.
- At J, hike boardwalk out and back.
- At J, turn left.
- At K, turn left.
- At E, turn right.
- At D, turn left.
- At C, turn right.
- At B, turn right.
- At A, continue straight.
- At N, turn right.
- At M, return to car.
Photo Album
