May 19, 2019
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Portland attorney stars in backcountry skiing Web series

On a clear day, Ben Leoni can look out the window of his 10th-story office in Portland and see the White Mountains, ripples on the horizon. The view lifts the young attorney’s spirit when he’s bogged down with work, because come Saturday, that’s where he’s headed — to the slopes, ravines and glades of the backcountry.

In the upcoming Web series, “Working for the Weekend,” 31-year-old Leoni and a team of fellow backcountry skiers will take viewers to remote locations throughout the Northeast to find challenging runs and explore the wilderness. The series is produced by Meathead Films and Ski the East, a Vermont-based clothing company that produces annual media and events to promote skiing on the East Coast.

“It’s my release,” Leoni said of skiing in a recent interview. “You have to have a good work-life balance.”

Leoni works as an attorney at the Portland-based law firm Curtis Thaxter, where he focuses on land use and zoning disputes, energy matters and administrative appeals. In 2011, he visited the Library of Congress to accept the Burton Award for Distinguished Legal Writing, the highest honor in legal writing in the U.S., from U.S. Supreme Court Justice Sonia Sotomayor.

In other words, Leoni works hard. So perhaps it’s only natural that he also plays hard.

“I’ve been skiing for a really long time,” Leoni said. “I’ve probably even toned it back a bit the past couple of years. I used to jump off cliffs way more, especially out West, where snow is a little softer and deeper. I am far more cautious about things like avalanches.”

The first season of “Working for the Weekend” will kick off in early December on and will consist of five webisodes, each 5-8 minutes in length. In that short span of time, Leoni and his team of male and female skiers will visit backcountry ski locations scattered throughout the Northeast, including glades in Maine.

The upcoming series has already caused some buzz on the Internet. The trailer has been featured on the website of Outside magazine, Powder magazine, and ESPN; and the series was also featured in the December 2013 edition of Skiing magazine.

Leoni came up with the concept for the series, which is now in the process of shooting the second season.

“I know a lot of people who were in my shoes,” Leoni said. “All of these people are in their late 20s and early 30s and are living a more professional life. We’re weekend warriors like the majority of people are, not ski bums that get paid to ski all the time.”

On Thursday, Leoni starts discussing weather and skiing conditions with his team — a group of skiers from Maine, Vermont and New Hampshire.

“There’s a lot of risk assessment that goes into this stuff,” he said. “There were a lot of days we didn’t go into Tuckerman Ravine or Gulf of Slides because we felt the risk was too high for avalanches.”

Another big challenge of filming backcountry adventures is simply carrying the heavy camera equipment to these remote locations. When shooting “Working for the Weekend,” the skiers, photographers and videographers divvy up the heavy camera equipment during the trek, distributing the burden.

In addition, even the most experienced videographers can be set back by the elements, and retakes aren’t so easy when you’re flying down a mountain.

“You get one snowflake on the lens, and it ruins the shot,” Leoni said.

By now, Leoni is used to the filming process. He has been skiing for Meathead Films and Ski the East since 2007, though he has never been the “star” of a production until now.

His passion for skiing was handed down by his parents, who met while working as ski instructors at Jiminy Peak in western Massachusetts. Leoni grew up ski racing, and the sport led him to love outdoor activity in general.

Prior to law school, Leoni taught sailing in midcoast Maine, worked as a backcountry caretaker on the Appalachian Trail, spent time skiing out West and completed the 2008 U.S. Freeskiing Tour.

Today, Leoni’s passion for outdoor recreation and the wilderness is reflected by his involvement in Beyond Ktaadn, the Northern Forest Center, Sail Maine and the Maine Chapter of The Nature Conservancy.

It was while attending Bates College that he became interested in backcountry skiing and met some of this closest ski buddies, many of whom he still skis with today.

“It’s really cool just being in the middle of the woods in the winter and exploring new places,” Leoni said. “[The Web series] is as much about exploring as it is about skiing in these episodes.”

“This project has forced me to do more exploring,” he continued. “I’ve found new places that I wouldn’t have normally skied.”

He spent last weekend in New Hampshire, filming adventures for the second season.

Watch the “Working for the Weekend” trailer at, and stay tuned for upcoming webisodes in December.

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