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Wellesley’s 7 official scenic roads

Wellesley has plenty of roads that might be described as scenic, but only seven are officially scenic designated by vote of Town Meeting per state law.

Here are the roads, when they were established as “scenic,” and their length:

Benvenue Street (Est. 1991, 0.81 miles)

This windy road links Dover Road to Brook Street, and travels past Tenacre Country Day School, off of Grove Street.

Benvenue St., Wellesley, autumn

benvenue

benvenue

 

Brookside Road (Est. 2011, 0.63 miles)

This most recently designated Wellesley scenic road abuts Rosemary Brook and the Wellesley Country Club, and features the Brookside Community Gardens. A community group called Friends of Brookside is active to protect the road and surrounding resources, including Longfellow Pond.

brookside community gardens

brookside road

Cartwright Road: (Est. 1989, 0.39 miles )

Branches off of Benvenue St., was once the sight of a flower farm run by the Cartwright family.

cartwright roadcartwright road

Cheney Drive: (Est. 1991, 0.09 miles)

The bridge and entrance to Elm Bank Reservation off of Rte. 16 on the Wellesley/South Natick line.

cheney bridge elm bank lights

scenic road cheney elm bank reservation

Pond Road: (Est. 1974, 1.17 miles)

Steep road nestled between Lake Waban/Wellesley College and stately homes and mansions. It connects Rte. 16 to Rte. 135 along the Natick and Wellesley border. (See also: Littering fines that even Wellesley residents can’t afford)

pond road lower end

Pond Road

lake waban sunset
Great view of Lake Waban

 

 

Squirrel Road: (1985, 0.27 miles)

This road, off of Woodlawn in the Wellesley Farms area, parallels the MBTA train tracks.

squirrel tree
Squirrels and friends carved into tree at Squirrel Road and (technically) Woodlawn Avenue (photos via KC)

squirrel road scenic

squirrel road scenic

The Waterway/The Brookway: (Est. 1978, 0.12 miles)

This road is in between Hillside and Glen Roads in the Wellesley Farms area, and is notable for its ruins from an old subdivision project. Josh Dorin has written a good history of The Waterway.

The waterway

The Waterway, Wellesley

The state law grants the Wellesley Planning Board approval authority, at a public hearing, to review the proposed removal and/or alteration of trees, stone walls or portions of stone walls along any designated scenic road.


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