The Weston Forest & Trail Association doesn't make many jokes in its trail descriptions. The one it makes about Highland Forest is a warning. The parcel, WFTA says on its Special Places page, "has a trail system guaranteed to get you lost!"
The same sentence also explains why. The woods are hard to read because the network grew out from a single oval woods road, and that road was General Charles Jackson Paine's harness-racing track. Once you can picture that mile-long ring at the center, the paths make sense. So does the fact that this oval sits on the first land the town ever bought for conservation.
A Rough Circle East of Highland Street
The best source on the track is a family member. In 1991, Thomas M. Paine, a great-grandson of the General, wrote a two-part history of the estate for the Weston Historical Society. In Part II, published in the August 1991 Bulletin, he lists the sports the Paines took seriously: tennis, bowling, trotting and shooting. Then he places the tracks:
"Paine maintained two trotting racetracks, a half-mile and a one-mile. The former lies east of the site of the house very near Chestnut Street. The latter is a rough circle in the center of the Town Forest east of Highland Street."
He adds that the sulkies "must have logged hundreds of miles on these tracks" and that they stayed in the estate barn into the 1960s. The same account describes a barn that held 15 to 20 horses and a separate building for carriages, sleighs and sulkies. The track's working life also lasted past the horse era. A Winter 2022 town conservation newsletter describes it as "the track used for both sulkies and cars."
The half-mile track near Chestnut Street left a smaller mark. Part I of the series, in the July 1991 Bulletin, identifies its remnant in a photo key as a curving driveway beside a field northeast of the barns. The mile-long oval is the one that survived as a trail.
How a Highland Street Farm Became an 1,100-Acre Estate
The oval took up a lot of land because the Paines owned a lot of it. Their holdings grew in steps over roughly three decades.
| Year | What happened | Source |
|---|---|---|
| 1868 | Charles and Julia Paine buy their "first 140 acres in Weston," the Jones–Marshall estate farm on Highland Street | July 1991 Bulletin |
| c. 1870 | A large ell is added to the old Jones mansion | July 1991 Bulletin |
| 1883 | The original mansion is offered to Charles H. Fiske, who moves it in two pieces to Church Street. Boston architect Carl Fehmer designs the replacement | July 1991 Bulletin |
| 1883–1894 | The Olmsted office's Job 1396, "Paine, Charles J. / Estate / Weston, Mass." | Library of Congress |
| April 1894 | Grounds plan credited to Olmsted, Olmsted & Eliot | August 1991 Bulletin |
| 1916 | The General dies, and son John Bryant Paine moves his family into the Big House | August 1991 Bulletin |
| 1955 | The town buys 147 acres on Highland Street from the Trustees of the Charles J. Paine Estate | Weston OSRP, 2026 |
| 1972 | The Big House is demolished | August 1991 Bulletin |
That first purchase in 1868 was already historic land. Part I traces the core parcel back to Jones family ownership around 1665, and says Col. Elisha Jones built its mansion between 1755 and 1760. The house stood east of Highland Street, "just behind the stone wall, about a thousand feet south of the Chestnut Street intersection." The Paines then bought the neighboring farms one at a time until the estate reached south past what is now Regis College, along both sides of Wellesley Street and South Avenue. In total they assembled "some eleven hundred acres."
The house at the center matched that scale. Thomas Paine describes it as gray and well past thirty rooms. He also writes that it was built so solidly that "the floors had not sagged by 1972," the year it came down. Its grounds followed the Olmsted firm's design. Part II mentions a grass tennis court "in the center of Olmsted's avenue in front of the house," a bowling alley building in the field to the south, and old stone walls rebuilt as retaining walls so the lawn looked unbroken from the house. The Library of Congress catalogs the Olmsted file as Job 1396, and American University's Olmsted plans list uses the same job number for the C. J. Paine Estate.
Golf was the one sport the estate didn't host. Paine took it up when his minister, Charles F. Russell, brought the game to Weston around 1895. He won the first club championship and served as an early president of the Weston Golf Club.
The Town's First Conservation Purchase Came With a Racetrack
Weston's 2026 Open Space and Recreation Plan, dated May 2026, traces the town's land conservation back to 1953, when Weston formed a Town Forest Committee. That committee drew up proposals for land on Highland Street and in the Jericho Town Forest area. Its early approach was to buy backland at a bargain price, on the theory that sitting next to a town forest would make the owner's remaining frontage more valuable.
The same plan calls 1955 "a milestone year in the history of Weston land conservation." That year the town made its first land purchase, 147 acres on Highland Street from the Trustees of the Charles J. Paine Estate, to create the Highland Town Forest.
The plan doesn't mention the racetrack. Paine's one-mile oval was simply inside the land the town bought, and it became the backbone of the Highland Town Forest. Jericho moved forward the same year by a different route. The plan notes that Marion Farnsworth donated 40 acres in 1955 to start the Jericho Town Forest, and that the town bought 48 acres off Sudbury Road from the Ogilvie family in 1960.
The Weston Forest & Trail Association also formed in 1955, the same year the Paine land changed hands. It started publishing town-wide trail maps by 1964 and has maintained all of Weston's trails since the 1970s. The Conservation Commission followed in 1961. So the organization that now cares for the trails began the same year as the forest that holds Paine's oval.
Reading the Spokes
Treat the oval as the hub and the network becomes manageable. WFTA lists the destinations of the paths that branch off "the oval woods road of the old track":
- Regis College, to the south, on land that sat along the edge of the old estate
- Chestnut Street, toward the former house site and the half-mile track
- Wildflower Lane, where the trailhead and parking are
- South Avenue and Wellesley Street, both inside the estate's southern reach
- Sanderson Hill, the westward viewpoint just off Highland Street
The 1991 Bulletin and WFTA's map description line up. Paine's land ran along Chestnut Street, Wellesley Street and South Avenue, and those are the streets the spokes lead to. Most of the paths through the woods connect old estate land to streets that once formed its edges.
Sanderson Hill is the spoke that predates the Paines. WFTA says it was a beacon site during the Revolutionary War. From the top you can see Nobscot Hill in Framingham and Mount Wachusett in Princeton. Mount Monadnock in southern New Hampshire used to be visible too, but "towering trees now obscure" it.
Some details are still unknown. None of the sources we found says who built the track or when, names the horses that raced on it, gives a measured length for the loop as it is today, or says which estate structures besides the demolished Big House still stand.
Getting There, and the Walks Still Ahead This Season
WFTA sends walkers to the trailhead on Wildflower Lane, reached from Highland Street. Park on the same side of the road as the trailhead. An earlier town calendar listing puts the trailhead about halfway down Wildflower Lane toward the cul-de-sac. Dogs are welcome on WFTA walks if they're leashed and under their owner's control.
Highland Forest was the first stop of the 2026–27 guided-walk season. WFTA trustees Ann Wiedie and Linda Nelson led the October 4 walk through the Paine Estate grounds and around the wooded loop of the track. That date has passed, but the rest of the season is set. Per WFTA's schedule announcement, walks run monthly from October through May. Unless noted otherwise, they start at 2 p.m. "rain, shine, or snow" and last one to two hours. The printed schedule went out as an insert in the Weston Observer on September 25.
The next joint outing is sooner. The Weston Media Center's community hub lists a WFTA and Council on Aging walk at Norumbega Tower Park on Tuesday, October 20, from 1 to 2:30 p.m. WFTA asks walkers to check its news page for last-minute changes before heading out.
If you go on your own this month, start from Wildflower Lane, find the oval, and use it as your reference point. Every spoke WFTA lists eventually comes back to it.
Stories like this one are part of how The Lara and Chelsea Collaborative understands Weston, down to the estates whose land became the town forests. If you own property near Highland Street or the old Paine lands and want to know how that history affects your home's story, we'd welcome the conversation. Request a Private Consultation.
