“I can’t believe we pulled that off,” beams Greg Hum, shaking his head as Framingham street lights come into view over his handlebars.

It’s 2 a.m. on Marathon Monday. Through force of will, Hum and his team have successfully shepherded hundreds of cyclists and their wheels from Boston to Southborough to follow the marathon route back to the city.

As he has done each year since founding the Midnight Marathon Bike Ride in 2009, Greg rides behind the hordes to sweep for flat tires, weary stragglers and the unicyclist, rollerblader and longboarder who tackle the 26.2 miles against all sane advice. I huff alongside and share in marveling at just how smoothly the ride has gone so far.

Faced with opposition from the Massachusetts Emergency Management Agency and the Boston Athletic Association, Hum and fellow organizers at the Boston Society of Shenanigans, plus a handful of other bike advocacy groups, doubled down and insisted that the ride would take place, one way or another.

But after the MBTA withdrew logistical support and refused to provide a dedicated train as it did last year, the ride’s captains had to get creative. In a masterstroke, they hired six moving trucks to ferry nearly 200 bikes from South Station out to Southborough, whose owners followed by commuter rail.


As I pull into the drop-off parking lot in Fort Point just after 10 p.m. on Sunday night, a swarm of volunteers give me a wristband and load my bike into a Uhaul. Another hands me a cue sheet with turn-by-turn directions and tips on crossing railroad tracks, and offers me lights in case I didn’t have them. I then follow the steady stream of fellow riders the four blocks to South Station, all of us anxious to board.

Check-in is cheery clockwork, incredibly smooth compared to loading hundreds of bikes directly onto the commuter rail as in years past. Our 11 p.m. train departs on time, filled primarily with fellow midnight riders bundled up for the long ride ahead.

It is bizarre, though, to take the train without cramming between pedals and wheels, but the roominess allows for easier conversation between participants. In the seat beside me is a woman from Maine and her son-in-law, both of whom had taken the train in from Portland just to complete the ride. Behind sits an athletic trainer and one of his clients, who make joking wagers on who would be most sore the next morning.



Word spreads quickly down the cars that hundreds of other cyclists had found alternate transportation, including some who pedaled all the way from Boston to the ride start. As we pull into Southborough station, a sea of blinking tail lights and glowstick-wrapped spokes confirm Hum’s hunch that the ride would go on regardless of official attempts to cancel.

With minimal hold up, the train unloads and we quickly retrieve our bikes from the waiting trucks. Police from Hopkinton and Southborough direct traffic out of the station and encourage riders to set out as soon as they can to ease congestion. Given the vocal public safety opposition to the ride, some had feared that officers would stop cyclists for minor traffic infractions or otherwise interfere. But that tension quickly melts as police from both departments hold cars back to allow riders onto the street in waves.

Greg’s sweep brigade sets off after all other riders have cleared out, logistical barriers conquered. At this point, my quickly numbing toes remind me that I forgot to put on a second pair of socks as planned. Leaving the Southborough station, our caravan heads toward Ashland, rather than toward Hopkinton’s famous square, as organizers had agreed to reroute the ride away from the start and finish lines.

As we merge onto the actual marathon route at Ashland, we come upon a unicyclist, Neil. Just a year earlier, over victory pancakes at the South Street Diner, Neil had sworn to never repeat the ride on a single wheel, so intense was his pain after finishing.

“That does sound like something I’d say,” he grins when asked about the change of heart. He then goes back to balancing and tilting his way toward Boston.

After passing through Framingham and into Natick, we spy a group that has pulled over to fix a flat by headlamp light. A truck we had seen multiple times since Southborough is parked close by, its door ajar to shed more light on the repairs.



As our sweep team pulls up, the truck’s driver is checking a tube for leaks. When he runs back to the truck to grab a wrench set, I ask the flat victim who the mystery mechanic is.

Blank stares.

I look at Greg, assuming this must be one of the ride organizers. But he shrugs, also bewildered.

When the driver returns, Greg asks if he’s with any of the bike advocacy groups.

“I just did the ride last year,” answers Donald Bishop. “I was too tired this year, but I figured I would drive along the route looking for anyone who needs help.”

Donald estimates that he has helped twenty or so riders tonight with a range of quick fixes.

Somehow Greg, who gladly volunteered dozens of hours ahead of this and every other Midnight Marathon ride, is baffled by such generosity. But this is spirit Hum has imbued into the fabric of the ride from the beginning.

Passing Wellesley and turning into Newton, I begin to look with dread for any rise in elevation suggestive of Heartbreak Hill. I swear each hill must be the ultimate summit, only to find another, steeper one behind it. The past two years have taught me nothing, apparently. After embarrassing strain that has me glad we’re pushing 3:30 a.m. and there are no cars around, we finally leave the uphill behind and begin the descent past Boston College and through Brookline.

We catch up to another organizer pulling a speaker system behind him in a bike trailer. He blasts James Brown and Outkast as we roll through Kenmore and onto Comm Ave, passing an unlit CITGO sign and neon-clad crews wrapping up marathon preparations.

Just as we had to skirt Hopkinton, we cannot veer onto Boylston Street and cross the marathon finish line itself. Instead, we continue straight to the Public Garden and along the Common, our aching bodies propelled by the benefit pancake breakfast that awaits us at Boston Common Coffee Company near Downtown Crossing.



We eat bacon and bananas and compare sorenesses. We cheer the organizers for pulling it off, for cementing a grassroots tradition despite the obstacles. And as we wheel slowly home to our corners of Boston, we look forward to a 2015 ride that taps once more into the collaborative energy that keeps the whole thing spinning.

 (video courtesy of LA Times)