• Contact Us
  • Events calendar
Entering Swellesley
Pinnacle, Wellesley

The Swellesley Report

More than you really want to know about Wellesley, Mass.

  • Advertise
  • Wellesley Square
  • Deland, Gibson Insurance Athlete of the Week
  • Camp
  • Private schools, sponsored by Riverbend
  • Business index
  • Contribute
  • Eat
  • Schools
  • Top 10 things to do
  • Embracing diversity
  • Kids
  • About us
  • Events
  • Natick Report
  • Seniors
  • Letters to the editor
  • Guidelines for letters to the editor
  • Live government meetings
  • Raiders sports schedules & results
  • Fire & police scanner
  • 2023 Town Election
 
Needham Bank, Wellesley
Write Ahead, Wellesley

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.


swellesley ad trees

Linden Square, Wellesley
Riverbend, Natick

Tip us off…

Please send tips, photos, ideas to theswellesleyreport@gmail.com

 

Advertisements

Wellesley Square, Wellesley Merchants
Wellesley, Jesamondo
Beacon Hill Athletic Club, Wellesley
Fay School, Southborough
Sexton test prep
Feldman Law
Wellesley Theatre Project
Volvo
Cheesy Street Grill
Mature Caregivers
Admit Fit, Wellesley
  • Facebook
  • Instagram
  • Twitter
Never miss a post with our free daily Swellesley Report email
Name: 
Your email address:*
Please wait...
Please enter all required fields Click to hide
Correct invalid entries Click to hide

You can subscribe for free, though we appreciate any contribution that supports our independent journalism.

Click on Entering Natick sign to read our Natick Report

Entering Natick road sign

Most Read Posts

  • Sign up now for summer camp in Wellesley (and beyond)
  • Letters-to-the-editor day in Wellesley—important election-time updates
  • Wellesley Public Works news: A PFAS warning; Weston Road construction on tap for summer; Wood recycling hot, pricey; Town Meeting article preview
  • Wellesley business buzz: Board business liaison phased out; Help ID top business leaders of color; Hospital taps new president
  • Wellesley Cotillion makes a strong comeback

Upcoming Events

Jan 25
7:00 pm - 7:45 pm

Olin College Presents Connecting Communities 2023: Sustainability

Jan 26
9:00 am - 10:30 am

Select Board office hours—in-person or online

Jan 31
9:00 am - 11:00 am Recurring

Coffee and Conversation with the Wetlands Administrator and Staff

Jan 31
7:00 pm - 8:00 pm

Families Eat Together online presentation

Feb 1
11:59 pm

Deadline for Wellesley Hills Junior Women’s Club grants application

View Calendar

Popular pages

  • Wellesley’s 7 official scenic roads

Recent Comments

  • Peggy Heffernan on Wellesley police officer injured in crash at intersection of Grove and Benvenue
  • Beth Dublin on Wellesley police officer injured in crash at intersection of Grove and Benvenue
  • Erika on Where to buy the Wellesleyest stuff in Wellesley
  • Alice Roy on Inside Track has jewel of a Wellesley engagement scoop
  • Sue Morris on Wellesley Cotillion makes a strong comeback

Links we like

  • Danny's Place
  • Great Runs
  • Jack Sanford: Wellesley's Major League Baseball Star
  • Tech-Tamer
  • The Wellesley Wine Press
  • Universal Hub
  • Wellesley Sports Discussion Facebook Group

Categories

  • 2021 Town Election (24)
  • 2023 Town Election (2)
  • Animals (428)
  • Antiques (49)
  • Art (592)
  • Beyond Wellesley (52)
  • Books (376)
  • Business (1,556)
  • Camp (11)
  • Careers/jobs (53)
  • Churches (82)
  • Clubs (236)
  • Construction (300)
  • Dump (130)
  • Education (3,189)
    • Babson College (252)
    • Bates Elementary School (18)
    • Dana Hall School (36)
    • Fiske Elementary School (11)
    • Hardy Elementary School (47)
    • Hunnewell Elementary School (46)
    • MassBay (57)
    • Schofield Elementary School (26)
    • Sprague Elementary School (19)
    • St. John School (2)
    • Tenacre Country Day School (11)
    • Upham Elementary School (35)
    • Wellesley College (613)
    • Wellesley High School (996)
    • Wellesley Middle School (204)
  • Embracing diversity (84)
  • Entertainment (814)
  • Environment (772)
  • Fashion (144)
  • Finance (15)
  • Fire (173)
  • Food (358)
  • Fundraising (640)
  • Gardens (164)
  • Government (603)
    • 2020 Town Election (47)
    • 2022 Town Election (15)
  • Health (866)
    • COVID-19 (203)
  • Hikes (6)
  • History (399)
  • Holidays (440)
  • Houses (162)
  • Humor (47)
  • Kids (867)
  • Law (8)
  • Legal notices (10)
  • Letters to the Editor (71)
  • Media (72)
  • METCO (4)
  • Military (13)
  • Morses Pond (109)
  • Music (579)
  • Natick Report (30)
  • Neighbors (280)
  • Obituaries & remembrances (86)
  • Outdoors (655)
  • Parenting (63)
  • Police (778)
    • Crime (395)
  • Politics (554)
  • POPS Senior Profile (10)
  • RDF (6)
  • Real estate (344)
  • Religion (138)
  • Restaurants (340)
  • Safety (154)
  • Scouts (2)
  • Seniors (127)
  • Shopping (163)
  • Sponsored (6)
  • Sports (1,011)
    • Athlete of the Week (12)
  • STEM (108)
  • Technology (165)
  • Theatre (397)
  • Town Meeting (23)
  • Transportation (239)
  • Travel (17)
  • Uncategorized (1,244)
  • Volunteering (350)
  • Weather (179)
  • Wellesley Election 2019 (21)
  • Wellesley Free Library (280)
  • Wellesley Holiday Gift Guide (2)
  • Wellesley's Wonderful Weekend (20)

© 2023 The Swellesley Report
Site by Tech-Tamer · Login