Where new drivers can practice in Wellesley

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