Each year, the night before the Boston Marathon, hundreds of cyclists meet at the race's starting line in Hopkinton for an unofficial, unsanctioned event: a midnight ride along the marathon’s 26.2 mile route.

While people have been biking the Boston Marathon route for a long time, it became a more regular tradition after 2009, when a group of Boston University students decided to go for a ride.

"We knew we loved biking but hated running,” said Greg Hum, who was one of those bikers.

“We wanted a way to connect with this amazing Boston tradition but didn't want to run it. So we decided to take our bikes on the train and bike the marathon home in the middle of the night.”

From there, the unofficial event just started to grow.

"We told our friends, and our friends told their friends, and their friends told their friends," said Galen Mook, who was also one of those original bikers and is now executive director of the Massachusetts Bicycle Coalition.

Over the years, Mook said, it grew into a huge, rolling party.

"Depending on the weather, of course, I think at the peak we've had about 2,860 something or so riders."

One logistical challenge has always been getting to the starting line, since not everyone wants to add the extra miles to bike there. One solution had been to take the MBTA's commuter rail to Southborough station, near the starting line. One year, the MBTA even provided a special train just to accommodate the midnight riders.

But this week, Mook says he was unhappy to see a new rule included in the marathon guide the MBTA put out.

"Specifically on the Framingham Worcester line, which would be the one that takes us out to Southborough, bikes are prohibited starting at 5 p.m. the evening before, on Sunday."

A spokesperson for Keolis, which operates the commuter rail for the MBTA, told GBH News that the prohibition is due to safety concerns over stowing too many bicycles on the train.

Mook is unhappy with the decision, but says even without the train, people find other ways to get their bikes to Hopkinton.

"People are incredibly nimble at figuring this out," Mook said.

Bikers on the commuter rail
Bikers take a late night commuter rail train to get near the marathon starting line in 2022
Galen Mook Courtesy of Galen Mook

Thirteen bikers participated in a practice ride last Saturday organized by the bike advocacy group CommonWheels. The trip started in Allston, riding out on Beacon Street to the town of Wellesley, and back to Boston along the marathon route on Commonwealth Avenue.

As the group rested at the halfway point in Wellesley, Marie Yatsyk of Somerville pointed out she was riding a mountain bike, which she noted wasn’t the easiest for a trip like this.

"Some of the hills are a little rough, especially on the heavier bike. But more or less, not too bad," she said mid-route.

Reiner See of Boston said he’s done the midnight ride once before.

"Back pre-COVID at midnight, it was so cold. It was raining the whole time,” he said. “But, you know, because there's so many people going there, and everybody had LED lights, music, you know, it was a fun ride."

See said he’s glad to see the forecast looks much better for this year's ride.

The leader for this practice ride, Laura Gray, said in some ways, the midnight ride is actually easier.

“At 2:00 in the morning, there's just not that many [cars] on the road,” she said. “So, you have a lot more space. You have the safety of all of the other riders around you. It's a really nice experience.”

"Any day, any night on the bike is a good day or night for me," said biker Daniel Day of Roxbury. "You get to see a different side of the world, you know. Biking is a beautiful way to explore.... You always go right? Take a left next time and just find out, you know, what's on the other side.”

After the break in Wellesley, the group hit the road again and headed back towards Boston on the Marathon route.

"We're just about at Heartbreak Hill,” Naomi Goodman said with trepidation as she pulled up to a stop light at Commonwealth Avenue and Centre Street.

For runners, part of what makes Heartbreak Hill so difficult is that it’s actually the third in a series of hills in Newton. The infamous hill is far easier for cyclists, who can coast the downside part of each hill.

The training ride wrapped up back in Allston after a little more than 22 miles. Most of these 13 cyclists said they will be back in the early hours of Monday, joined by hundreds—and maybe even thousands—of other bikers going the full 22.6 miles in this unsanctioned, grassroots tradition, ending at the finish line of the Boston Marathon in Copley Square.