Adventure and endurance races across Maine invite participants to run, swim, paddle, bike, navigate, and sometimes even crawl their way through scenic woods and waters. These four diverse events, open to all ages and abilities, encourage racers to push their limits in the company of fellow outdoor enthusiasts.

Teamwork is the key to success in
the East Grand Adventure Race.
Photo courtesy Dave Conley

East Grand Adventure Race

Danforth, ME • May 10, 2025

Picture yourself on the starting line, flooded with adrenaline beside dozens of fellow adventurer racers. Ahead lies a swathe of Washington County wilderness and, somewhere out there, the finish line. The East Grand Adventure Race in Danforth comprises 10 miles of bike trails, a one-mile compass navigation trail run, and an eight-mile paddle along the Baskahegan Stream. Along the way, competitors may have to throw a tomahawk at a target, complete a wildflower ID challenge, scale an eight-foot wooden wall, or crawl on elbows through a soupy mud trench.

For 18 years, the East Grand’s devious course creators have dreamt up all kinds of challenges to test the mettle of competitors, young and old. A family favorite, East Grand welcomes participation at almost any age and team size (kids under 12 must partner with a parent or mentor). With so many obstacles to overcome, the race favors gumption and a give-it-a-go attitude above all else.

“I think people are hungry for adventure,” said Ray Wirth, 2024 East Grand Adventure Race champion. “I know I am. This race drew me in because of that adventure component…There are more unknowns, more challenges you can’t fully prepare for.” Nonetheless, the overriding atmosphere is inviting. “You’re out there competing against others, but you’re also sharing a common journey with them,” he said. “It’s more about the experience than the outcome.”

Trek Across Maine leads cyclists on a
180-mile journey to benefit the American Lung
Association. Photo courtesy of Silo Media.

Trek Across Maine

Starts and Ends inNew Gloucester, ME

June 13-15, 2025

Now in its 41st year, Trek Across Maine is a legacy staple of Father’s Day weekend in Maine. The challenge leads cyclists on a three-day, 180-mile journey that meanders from Pineland Farms in New Gloucester and back on a winding route that includes two overnight stops at Bates College in Lewiston and St. Joseph’s College in Standish. Riders must raise a minimum of $550 to participate, funds that support the American Lung Association’s research, advocacy, and education efforts. To date, the event has raised more than $32 million. For many riders, the Trek has become a decades-long tradition motivated by a personal connection to the cause. As Evan Lelansky explained, “My mom passed away from lung cancer in 1996. I began riding the Trek Across Maine and supporting the Lung Association in her memory the very next year. My son began riding with me three years later and has continued to ride with me for the past 24 years. We get to spend Father’s Day weekend together each year, supporting a great cause and riding in my mom’s memory.”

As an established calendar fixture, the Trek is a well-oiled machine that offers riders a clear order of events. If you love a challenge that doesn’t involve getting lost alone in the woods, you’ll appreciate the small army of volunteers, support vehicles, and three daily rest stops with refreshments that Trek Across Maine can provide. Pedalling, on the other hand? That’s all down to you.

Competitors test their limits during
the 24-hour race challenge at the
Maine Summer Adventure Race.
Photo courtesy Legendary Randy Ericksen Films.

Maine Summer Adventure Race

Bethel, ME • July 12-13, 2025

Venture into the rugged Maine countryside armed with only a compass and map for a nonstop expedition on foot, mountain bike, and canoe. Launched in 2017 by Strong Machine Adventure Racing, a Portland-based nonprofit, The Maine Summer Adventure Race raises funds for local land trusts and environmental education.

Each year, Strong Machine founders and adventure racing duo Kate and Cliff White, design a challenging new course in different locations across Maine. “We describe adventure racing as an off-road scavenger hunt, where teams try to collect as many checkpoints as possible within the time limit of the race,” said Cliff White. “Each course is completely unique.”

A tiered race system allows racers of all levels to participate in groups of two to four at varying intensity levels. Beginners can test the waters with a three-hour race. According to race descriptions, past finishers have included toddlers and septuagenarians. An intermediate eight-hour and 24-hour race class ups the ante for those who want to test the limit of their endurance by traveling between 50 to 100 miles across land and water.

Swimmers brave cold and strong currents
to complete the Peaks to Portland
Swimfor Kids and raise money for
YMCA youth programs.
Photo courtesy YMCA of Southern Maine

Peaks to Portland, A Swim for Kids

Portland, ME • July, 26, 2025

There are few things more relaxing than gazing across Casco Bay. Swimming across it? That’s another story. However, a worthy cause has motivated swimmers to do just that for decades. The Peaks to Portland, A Swim for Kids, a 2.4-mile open-water swim in bracing waters, is a beloved local tradition and one of the landmark fundraising events that benefits the YMCA of Southern Maine. Swimmers will be delighted to learn the race will return in 2025 for the first time since the COVID-19 pandemic.

One of the oldest open water races of its kind, the first Peaks to Portland swim was recorded in the early 20th century, according to the Southern Maine YMCA. The organization relaunched the tradition in 1981 as a fundraiser to support the financial assistance program that provides kids and families access to day camps, preschool, after-school activities, and swim lessons regardless of their ability to pay. This year’s fundraising goal is $225,000. Francisco Guzmán was a veteran of the endurance race scene when he first decided to take on the challenge in 2018. “My children at that time were at the age of enjoying the YMCA summer camps, and the thought of helping other children attend was motivating,” he said. His most challenging part of the swim? “The currents, without a doubt.”

Prefer to stay on dry land? The sight of hundreds of hardy souls crossing the sparkling blue bay surrounded by colorful support kayaks is a moment of pure summer magic. Send off the swimmers on Peaks Island or welcome them back to land from the finish line. “Spectators typically gather on East End Beach so they can cheer swimmers as they land,” said Meaghan Woodsome of the Southern Maine YMCA. A DJ announces the swimmers as they land ashore, followed by a ceremony for the fastest crossing in each age group. “It’s very festive,” she added.

Story by Saisie Moore, a writer and editor based in Portland, Maine. When not tapping a keyboard, you can find Saisie outdoors cultivating her ecological gardening business, Pollen.