• Sign up for free email newsletter
  • Advertise
  • Donate to support our work
  • Events calendar
  • About Us
 
Pinnacle, Douglas Elliman, Wellesley
 
Wellesley Hills Dental

The Swellesley Report

Since 2005: More than you really want to know about Wellesley, Mass.

  • Restaurants, sponsored by black & blue
  • Camps, sponsored by NEOC
  • Wellesley Square
  • Private Schools, sponsored by Prepped and Polished
  • Public Schools, sponsored by Sexton
  • Preschools, sponsored by Longfellow, Wellesley
  • School news
  • Kid stuff
  • Top 10 things to do
  • Business news
  • Worship
  • Letters to the editor
  • Guidelines for letters to the editor
  • Live gov’t meetings
  • Sports schedules & results
  • Deland, Gibson’s Athlete of the Week
  • Deaths
  • Housing
  • Medical providers—sponsored by FIXT Dental
 

Top Stories

Wellesley commemorates 25th anniversary of Sept. 11 attacks
Special Town Meeting warrant revealed
Revamped playground opens at Warren Park

Advertisements

Needham Bank, Wellesley
FIXT
Down Under, Wellesley

Where new drivers can practice in Wellesley

April 24, 2022 by Bob Brown

We were recently asked by a reader who is learning how to drive about the best places in Wellesley to practice this important skill.

Our initial thoughts went back to where we taught our kids to drive, largely at the Wellesley High School parking lot on weekends or other off-hours, as well as at the MassBay parking lot on Oakland Street, also on weekends. We also tried to learn about where our kids’ driving school did its testing, and practiced on some of those streets.

But we know our world is limited, so reached out to others, including the Wellesley Police Department and a local driving school. We haven’t heard back from either yet, but will update this post if we do. We know this is one of those subjects where people might get nervous about suggesting anything due to liability concerns, so might be inclined to keep mum.

The richest source for ideas came from readers on our Facebook page, so here’s a summary of their suggestions:

  • The town-owned train station parking lots on Linden Street (Tailby Lot) and at Wellesley Farms (Squirrel Road). These lots are nearly empty on weekends, and during much of the pandemic, have been thinly populated even on weekdays.
Wellesley Farms Train Station, parking lot
A wide-open Wellesley Farms train station parking lot

 

  • Area cemeteries, such as Woodlawn off of Brook Street. “Lots of intersections and sometimes narrow roads to practice getting a sense for the cars size relative to the edge of the road,” wrote one advocate. Though of course as soon as we started asking about this topic, a new driver plowed into some headstones at a Melrose cemetery.
  • MassBay Community College parking lot on Oakland Street.  Includes lots of parking space lines to practice parking. Babson’s got some big lots, too, but we didn’t tell you to go there.
  • Wellesley High School or Weston High School/Middle School parking lots during off-hours.
  • Elm Bank Reservation on the South Natick/Wellesley line on Rte. 16. I find Elm Bank to be dicey for new drivers since the road is relatively narrow, and there are lots of walkers, dogs, runners, cyclists there depending on when you go. One reader warned about the potholes here, too. Though the parking lots at the top can be good for new drivers during off-hours, and there’s no pressure to go fast here.
  • While some suggest practicing at local office parks, others warn to avoid this private property.

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

image_print

Filed Under: Education, Transportation

Comments

  1. Greg Livingston says

    April 24, 2022 at 8:44 pm

    I taught my four kids to drive in three stages: 1) the St. James parking lot (now the pool) for the earliest basics of braking and steering; 2) the Generals neighborhood off Weston Road, for the wide streets; and 3) when they were ready, we went down Route 16 all the way to Milford, then back again. Lots of varied experiences but nothing over 30 mph and you could stop anywhere along the way.

  2. Tom Stagliano says

    April 24, 2022 at 5:16 pm

    Of course, make certain that your child has their learner’s permit. Do NOT attempt to teach your child to drive in one of those parking lots (Mass Bay or the high school) if they do NOT yet have their learner’s permit.
    Make certain they stay under control and watch out for parents who are teaching young children how to ride a bicycle in the same lot.
    Once they have mastered basic control (and use the parking spaces to give them a sense of size relative to your car), then I took them to the streets in the Poets’ section of town From Tennyson to Damien. Enjoy the process.

  3. Cimarron Buser says

    April 24, 2022 at 4:16 pm

    Taught the kids to ride a bike (not a car) at the Wellesley Farms parking lot!

     

Advertisements

black & blue, Wellesley
Olive Tree Medical, Wellesley
Haskins Automotive, Wellesley
MIT Museum, Cambridge

Tip us off…

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

Please support your local online news source with a tax-deductible donation by scanning the QR code
or by clicking on it.

QR Code

Advertisements

Wellesley Square Merchants
Wellesley, Jesamondo
Fay School, Southborough
Sexton test prep, Wellesley
Wellesley Theatre Project
Prepped and Polished
Perdocere, Wellesley
Wellesley HIlls Dental
Admit Fit, Wellesley
entering-swellesley-1
  • Bluesky
  • Facebook
  • Instagram
  • Twitter

Subscribe to our free weekday email newsletter

* indicates required

Follow Swellesley on Google News Showcase

The Swellesley Report has been selected to be highlighted on Google News Showcase. Please follow us there.

Most Read Posts

  • Friday is letters-to-the-editor day
  • September 11th ceremony at Wellesley Fire Department—25th anniversary
  • Obituary: Alan Rogers of Wellesley, emeritus professor of history at Boston College
  • Wellesley Arts Roundup—September edition
  • What if someone wanted to build a data center in Wellesley?

Click on Entering Natick sign to read our Natick Report

Entering Natick road sign

Recent Comments

  • Deborah Brown on Wellesley College pledges free tuition for more families
  • Jill Dothington on What if someone wanted to build a data center in Wellesley?
  • Jill Dothington on What if someone wanted to build a data center in Wellesley?
  • Kim Mahoney on What if someone wanted to build a data center in Wellesley?
  • TZ on What if someone wanted to build a data center in Wellesley?

Calendar

Upcoming Wellesley events

Upcoming Events

Sep 13
8:00 am - 12:00 pm

MassBay Community College annual All Vehicle Show

Sep 13
10:00 am - 3:00 pm

Natick Art Association’s Art in the Park —Shaw Park

Sep 13
2:00 pm - 4:00 pm

Charles River Sinfonietta concert at Wellesley library

Sep 14
1:00 pm - 3:00 pm

Learn to Play Rummikub

Sep 14
7:00 pm - 8:00 pm

Wellesley Choral Society rehearsals

View Calendar

Links we like

  • Danny's Place
  • Great Runs
  • Tech-Tamer
  • Universal Hub
  • Wellesley Sports Discussion Facebook Group

© 2026 The Swellesley Report
Site by Tech-Tamer · Login