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Darrow Montgomery was walking down an alley off K Street NW when he looked up and saw a contrail. This is not a remarkable sight, but the little white streak in the sky between towering downtown buildings did make for a remarkable photo. That was five years ago, and Montgomery has been capturing contrails ever since.

As City Paper’s photographer of 32 years, this isn’t his first essay. He’s spent weeks, months, or years studying D.C. bus stops, the 600 block of H Street NW, disappearing commercial signs, people obsessed with their smart devices, and other topics. Contrails are different because he can’t control when he finds them. “You just have to be ready for them, and you have to do it right then or it will be gone—or it will be different,” he says.

He took the photos with his iPhone. “Most of these are from when I’m out riding my bike,” he says. “In the old days, I wouldn’t have gotten them because I wouldn’t have been able to bring a big camera with me.”

Some contrails in this collection are bright streaks against a blue sky, or billowed out airplane trails big enough for a toddler to recognize. Others are thin, disappearing stripes that catch sunlight as they slip in and out of the clouds. In one photo, a woman (who happens to be reading City Paper) and a boy unknowingly have twin contrails in the sky above their heads.

In a few photos, it’s hard to tell whether you’re looking at regular clouds or the remnants of a flight. But Montgomery didn’t count anything ambiguous. Look for the indisputable contrails. — Alexa Mills

Ohio Drive SW, Jan. 20, 2018
Metropolitan Branch Trail, March 7, 2016
K Street NW (rear), June 4, 2013
Dupont Circle, March 2, 2015
15th Street NW, Nov. 17, 2017
Washington Monument, Jan. 20, 2018
National Mall, Jan. 20, 2018
Florida Avenue NW, Sept. 29, 2017
Logan Circle, June 19, 2017
Franklin Square, Dec. 4, 2017
Thomas Circle, Dec. 13, 2017
McMillan Reservoir, Feb. 13, 2018
Bladensburg, Md., Oct. 21, 2017
Unknown location, Dec. 16, 2017
RFK Stadium parking lot, Aug. 25, 2018
H Street NE, Feb. 14, 2014
Franklin Street NE, July 29, 2018
Bladensburg, Md., Oct. 21, 2017
Alexandria, Va., June 26, 2018
Mount Pleasant Street NW, Jan. 20, 2018
H Street NW, Oct. 29, 2015
Irving Street NW, March 2, 2015
East Potomac Golf Course, Jan. 20, 2018
16th Street NW, April 13, 2018