After the tragic death of a cyclist last fall, the town of Wellesley is trying to figure out how to make it safer for cars and bikes to share the streets. But as fervent as Wellesley’s desire for solutions is – making changes that really work may not be easy.

Matt Kressy is a Wellesley resident and an avid cyclist. He commutes to work at MIT and races regularly; last year, he rode more than 6,000 miles. As he tells it, biking in Wellesley is a mixed bag.

"When you’re driving around, everyone’s really kind and respectful for the most part," he said.

But Kressy says that while Wellesley drivers are an accommodating bunch, the town’s design isn’t that bike-friendly. Recently, Kressy agreed to show us what Wellesley looks like from above his handlebars.

"I’m gonna get a head start, so I can get up that road," Kressy says as he rides, constantly strategizing to prevent accidents and protect himself – which means staying away from high, sharp-edged curbs.

"I could catch a pedal on the curb pretty easily," he said. "It makes people pretty nervous. You’d die."

Because Kressy rides away from the edge of the street, he often occupies a hefty chunk of what many drivers consider their roads. But he says that on Wellesley’s cramped streets, that’s the best way to avoid being clipped by a passing car.

"What I tend to do is ride like this, and people get pissed off, but guess what?" he said. "You’re not going to run over the back of me."

If Kressy’s approach sounds extreme, the death of Alex Motsenigos suggests it isn’t. Last year, Motsenigos was struck and killed at Weston Road and Linden Street – known in town as a dangerous intersection. Despite a checkered record, the driver who hit him wasn’t charged – and now, Wellesley is taking a hard look at bike safety. A few weeks ago, the town hall was packed for a forum on how Wellesley welcomes cyclists – or doesn’t.

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"I felt safer in Los Angeles than I do in Wellesley," said one resident. "There aren’t dedicated bike lanes, but there is room, which we don’t seem to have in Wellesley."

The emotional crescendo of that meeting came when Alex Motsenigos’s brother, Spiros, thanked the town for trying to make Wellesley a safer place to ride.

"I want to ask that you don’t give up on this, and that you see it through," he said. "I think that’s very important."

But making Wellesley bike-friendly won’t be easy. The town’s narrow roads are already packed to capacity, which forces bikers like Kressy to make some unusual decisions as they ride. Here, Kressy moves from the right of the road to the center to work through a traffic jam.

"Another option is, I swing over here to the left side, where guess what: It’s almost always clear," he said. "Everyone sort of keeps a nice distance between their cars and other cars. That’s how I like to go through traffic, as counterintuitive as it may seem."

What’s more, Kressy says, the way some Wellesley roads are marked makes it tough for bikes and cars to coexist.

"On this road, you see how the lane kind of disappears all of a sudden for me?" he said. "That makes things confusing for the motorist. Now it opens up and things are good again."

For the record, Kressy strives to be a good citizen of the road. He stops religiously for pedestrians, signals every turn, and tries to let cars get by him when he can.

"Now, on an open road like this, I will actually stay on the white line to encourage people to pass," he said.

Kressy says he’s heartened by Wellesley’s bike-safety push. But he adds that while a smart redesign of the town’s roads could help, motorists’ attitudes need to change, too.

"Maybe this is a job for Mass Highway or something, you know?" he said. "Create some sort of program that really touches the hearts of all the people of the commonwealth, that makes them feel enthusiastic about other modes of transportation."

And until that happens — the tension between bikes and cars may be here to stay.