Skip to content

PHOTOS: Boston’s 2023 Bike To Work Day

Between 7:30 and 8:45 a.m., convoys of riders coming in from Mattapan, Dorchester, Brookline, Cambridge, Malden, Chelsea, and other cities across the region arrived in City Hall Plaza in waves, while City of Boston Transportation Department staff welcomed them with cowbells and cheers.
A crowd of people in bikes pedals through a wide brick plaza. In the center, wearing a black helmet and blue hoodie, is Boston Mayor Michelle Wu.
Mayor Michelle Wu, who was riding in from Roslindale, arrives in City Hall Plaza for Bike to Work Day on May 19, 2023.

It was a perfect spring day in New England for Bike To Work Day, and in Boston, hundreds of riders from all over the region met up in convoys from cities all over the region and convened for a festival in City Hall Plaza before work Friday morning.

A crowd of bike riders gathers in a parking lot beneath a 7-11 sign. Several of the people are riding Dutch-style cargo bikes with large front-mounted boxes in which their children are sitting to come along for the ride.
The Jamaica Plain Bike to Work Day convoy, which included several families with kids, gathers in the 7-11 parking lot near South Huntington Avenue and Centre Street at 7 a.m. on the morning of May 19, 2023.

The convoy riding in from Centre Street in Jamaica Plain included several families carrying young kids in Dutch-style cargo bikes. One of them was Eric Herot, a dad who works from home but wanted to come out to join his neighbors for the ride.

A man wearing salmon-colored pants and an orange jacket pedals a white Dutch-style cargo bike along a bike lane next to a parked car. His young son, visible only from the white bike helmet he's wearing, is sitting in the cargo bucket in front of him.
Eric Herot of Jamaica Plain pedals down Columbus Avenue in the South End.

“I actually work from home, so this is a recreational ride for me, although I do always like to show up and support it and make sure that other bicyclists who want to do it are in a group that makes them feel safer,” Herot told StreetsblogMASS.

We also met Joan Trueblood, a Jamaica Plain retiree who used to use the city’s Bluebikes bikesharing system to commute to her former job in Copley Square.

“I’m retired, but I just love this ride,” said Trueblood. “I’m very much in favor of promoting bicycle commuting and recreation. It’s a win-win-win.”

A woman wearing a teal jacket, purple backpack, a baseball cap, and a purple bike helmet pedals a Bluebike down the street next to a row of parked cars.
Joan Trueblood, a retiree from Jamaica Plain, pedals down Columbus Avenue in the South End for Bike to Work Day.
A crowd of over 100 people, many of whom are walking with their bicycles, gathers in a large brick-paved plaza. In the distance are the skyscrapers of downtown Boston.
The Bike To Work Day crowd in City Hall Plaza at 8:30 a.m. on the morning of May 19, 2023.

Between 7:30 and 8:45 a.m., convoys of riders coming in from Mattapan, Brookline, Cambridge, Malden, Chelsea, and other cities across the region arrived in City Hall Plaza in waves, while City of Boston Transportation Department staff welcomed them with cowbells and cheers.

The event also gave us a chance to appreciate the newly-renovated City Hall Plaza, which formally opened on a bitterly cold winter day last November, but is now bursting with greenery from newly-planted trees and gardens (and thanks to the new plaza’s accessible design, it’s now a much easier place for people to wheel their bikes around).

A crowd of over 100 people, many of whom are walking with their bicycles, gathers in a large brick-paved plaza. Several tents around the edge of the plaza advertise local bike shops. In the distance are the skyscrapers of downtown Boston.
City Hall Plaza on the morning of the 2023 Bike To Work Day.
Photo of Christian MilNeil
Christian has edited StreetsblogMASS since its founding in spring 2019. Before that, he was a data reporter for the Portland Press Herald in Maine. Got tips? Send them to me via Signal, the encrypted messaging app, at 207-310-0728.

Read More:

Streetsblog has migrated to a new comment system. New commenters can register directly in the comments section of any article. Returning commenters: your previous comments and display name have been preserved, but you'll need to reclaim your account by clicking "Forgot your password?" on the sign-in form, entering your email, and following the verification link to set a new password — this is required because passwords could not be carried over during the migration. For questions, contact tips@streetsblog.org.

More from Streetsblog Massachusetts

Thursday’s Headlines Shout, Shout, Let It All Out

April 23, 2026

Mayor Wu’s Latest Budget Plan Eliminates Funding for Over a Dozen Street Safety Projects: See the List

April 22, 2026

A Small Central Mass. Town Is Tearing Up A Parking Lot to Make Its Downtown Greener and More Walkable

April 21, 2026

Green Line’s B Branch Takes a 9-Day Break Starting Wednesday, April 22

April 21, 2026

Tuesday’s Headlines Curb Their Enthusiasm

April 21, 2026
See all posts