Pittsfield — Bryson is six years old; today he is racer #29, and he has just finished in second place. The race was close, and Bryson’s brother Karson, who was standing at the finish line, swears that #29—his brother—crossed it first, before #198, who has just been declared winner.
The boys argue with the referee, but then they move on, almost instantly, as if contending the loss is a rite of passage they must execute before they can proceed with the rest of their days. After all, the ref is Bryson’s uncle Marvin, and the winner, #198, is a friend from the neighborhood. Bryson seems nonplussed. On their way to the Westside Soap Box Derby this morning, Bryson’s grandmother Dolores Wright had prepared him for this outcome: “Sometimes you gotta lose,” she told him.

From 12 to 4 p.m. this Saturday, August 9, babies, grandparents, friends, aunts, exes, cousins, and “cousins” gathered at the junction of Robbins and Columbus avenues in Pittsfield for the fourth annual Westside Sweet G Super Soap Box Derby. The day was hot, exceedingly so, and the crowd was smaller than last year’s. If not the total culprit, the heat was a compelling scapegoat.
Never mind the number of attendees, the ones who did show up did so with a vengeance. Tony Jackson, president of the Westside Legends nonprofit group, corralled the troops, maneuvering the mic with swagger. Just past 1 p.m., his voice boomed: “Is everyone having a good time?” Claps, woots, in response. But it wasn’t good enough for Jackson: “C’mon, that’s a little weak for the Westside!” Eager to prove themselves, the kids tilted their heads back, cast their bellies up toward the sky, and bellowed at the heavens. One dropped his ice cream cone—Cotton Candy flavor, from Cravin’s Ice Cream stand—mid-howl.

That Tony Jackson has a skill for rallying the crowd is no news: The Westside Legends currently boasts nine board members, most of whom were Jackson’s classmates at Taconic High School. He called them up and they formed a group committed to fighting for housing for Pittsfield residents. They fight, for their own families and for their neighbors, but also, they have fun. Sometimes that means painting murals, massive and colorful ones, displaying scenes reminiscent of those taking place in the streets below. The Legends host block parties and soap-box derbies. By now, though, most of the board members live far away, in places like New Jersey and Georgia, which makes the whole thing more complicated and may explain the lower-than-usual turnout.

Luckily, they have a community of people eager to support. Tonya Frazier prints the roster in Expo marker on a whiteboard. She works for Habitat for Humanity just down the street, at 314 Columbus Avenue. “29, 38, 43, 50, 198,” she writes out— this is the six-year-old category. It seems like she knows most of the names behind these numbers and the faces and squeaky voices behind these names. She always helps out on derby day. Rebbeca Brien works for the community organization Downtown Pittsfield Inc., and today she distributes free water bottles to thirsty racers and spectators. Consuming these water bottles by the case are dads, who work as flagmen at the starting line. The sun is scorching. Sweaty brothers help T-shirted sisters into their soap-box cars.

Along the street, neighbors, even people without kids or grandkids or nieces or even “nieces” racing, sit on their stoops, or on the curb, and watch. Ernie Norton is 74. I find him—this is not so hard to do—sitting on his front step, guarded by his precious motorcycles, but otherwise, right in the middle of the action. He has lived in this house on Columbus Avenue for 34 years now. He was born in a different section of West Pittsfield because that is where the white people lived back then; this, Columbus Avenue, was where the Black people lived. “Now it’s gotten more mixed up. Everyone gets along,” Ernie says. He likes it. I ask him, would he ever leave? He looks at me like I have three heads.

While the impetus for the gathering is theoretically a “competition,” the air is anything but that. #43, six, says to #29, six, “I’m gonna smoke you.”
Inching up to the starting line, #29 spits back, “No, I’m gonna smoke you.”
The two boys belly laugh. A grown-up holds on to each of the back of their vehicles, waiting for the flag-dad to wave his flag, at which point they will release the boys down the course. Tony Jackson’s voice booms, “Go!,” and it is only seconds before the two elementary schoolers crash into each other. They take too long to get up because they are busy belly laughing on the ground. One of their mothers says, “See, I told you to look straight, don’t look at him!” #43 does not seem to hear her—belly laughs drown out noise.

Fortunately, of derby day’s three age groups, the last is adults: “18 and older.” Because they, hopefully, will not crash à la #29 vs #43, they can afford to drive more ornate vehicles. Dolores Wright says that Blue Q, a local gift manufacturer, is known for an annual showstopper. This year, the car resembles a hefty sandwich, of the kind this neighborhood loves from Angelina’s Submarine Shops. Blue Q, with its tomato wheels and glutenous exterior, wins Best in Show. Interprint, a local printing company, wins first place—as in, they were fastest.
The allocation of this prize (“first place”) was the most traditional element of this entire day, which was, in a word, lovely.






