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Special Places


Weston's special places...for you to find and enjoy


Since its creation, the Weston Forest and Trail Association has carefully developed and nurtured the extensive walking, horseback-riding and cross-country skiing trail system — some 103 miles of trails — that threads its way through 2200 acres of conservation land in Weston. See a map here. Here are a few of our favorites:

Distant view of Boston skyline from Doublet Hill, with rolling woods and a few buildings and towers in middleground

Doublet Hill, Elliston Woods and Hemlock Pond


Totaling about 60 acres, this tract is a varied and challenging spot. From the end of Doublet Hill Road, a walker can climb quickly to the rocky outcrop offering a view of downtown Boston. Those who want more exercise can descend either south toward the aqueduct and Hemlock Pond or eastward into a network of trails. The approach from Young Road offers the walker a longer route up to the hilltop or a meander into the woods dedicated to Weston Forest and Trail’s founder, Dr. William Elliston. Take note of the two wrought iron chairs at Hemlock Pond, a cherished remnant of the days when it was a neighborhood swimming hole.

Lee's bridge with brown lab sitting atop it
Photo of Lee in woods

Lee's Bridge


Built in 2013 with funds donated by the Cohen family in memory of Lee Cohen, a dedicated environmentalist and long-time Trustee of the Association, this stone bridge spans Three Mile Brook, on the Sears Conservation land behind Crescent Street. This is a favorite hiking area on land formerly part of the Sears estate. Water wheels which powered some of the industries in Weston in the 1800s were located here.

Lee was very instrumental in the development of the trail system in Weston, and his family donated a large tract of land behind Fields Pond Road, adjacent to the Weston Reservoir. He also was a strong supporter of land conservation, both in Massachusetts and in Maine where the Cohen family has a summer home. Read more about the story of Lee's bridge in this news post.

Stone wall in Highland Fores with people walking on trail at right

Highland Street Forest


Because it once held a harness-racing track, Highland Forest has a trail system guaranteed to get you lost! Branching off from the oval woods road of the old track are paths leading to Regis College, Chestnut Street, Wildflower Lane, South Avenue, Wellesley Street and Sanderson Hill, the westward viewpoint just off Highland Street. A beacon site during the Revolutionary War, Sanderson Hill affords a view toward Nobscot Hill in Framingham and Mount Wachusett in Princeton. Towering trees now obscure the once-visible glimpse of Mount Monadnock in southern New Hampshire.

Dam at Hobbs Pond from below, with water rushing from it

Cat Rock and 80 Acres


In reality this area is only 64.4 acres, but it has everything: a hill to climb, pine woods, a broad meadow, a roaring brook and a broad pond. The best approach is from the north end of Drabbington Way, which offers ample parking. Because of the pond, the Cat Rock area is a popular dog-walking area. Decades ago the hill was a municipal ski area; remnants of rope tow machinery can still be seen. Although it isn’t the highest summit in Weston, there’s a vista from the top of the hill toward Waltham and portions of Route 128.

Want to go further afield?

Wooden bridge across stream in woods with trail beyond

Photo © Wellesley Conservation Council

On our doorstep:

Carisbrooke Reservation and George L. Lienau Memorial Sanctuary


These two parcels form a single area of conserved land that straddles Wellesley and Weston. The Lienau Memorial Sanctuary, which is the portion in Weston, is owned by Wellesley Conservation Council and consists of a 1.3-acre strip along the town line. The Council’s website has more info about Carisbrooke Reservation and the Lienau Memorial Sanctuary, and longer descriptions of the land and trails can be found in the book Walks in Wellesley by Margaret Klein Wilson, available for purchase from the Council and at Wellesley bookstores. The Reservation and Sanctuary contain a pleasant variety of ponds, streams, rock outcrops, and forest along trails that connect up with WFTA trails in Weston.

Fairyland Pond in Hapgood Wright Town Forest with beds of reeds at far shore

Slightly further away, in Concord:

Hapgood Wright Town Forest


Excerpt from the guide to Hapgood Wright Town Forest (PDF):


“A walk in the Hapgood Wright Town Forest can be a peaceful experience exploring its many natural features, a world apart from the busy roads just above the ridge. This guide describes these features as well as cultural and historical points of interest. Its environs witnessed the lives of freed slaves who settled here struggling to farm its infertile soil. Henry David Thoreau, Ralph Waldo Emerson, and the Alcott and Emerson children were frequent visitors. Thanks to Thoreau’s written observations, we have a mid-1800s snapshot of the natural features and lives of the people who lived here, broadening our understanding of what we see today.”

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