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Camp Challenge

Two women in yellow tutus smile and wave while running at Camp
A family of three poses with their Challenge medals in front of the Creative Complex

When: Spring 2026
Where: The Hole in the Wall Gang Camp
Ashford, Conn.

As we say at Camp, challenge by choice! And the choice is yours to see Hole in the Wall a little differently by participating in our very own Bandit 5K Run/Walk or 6-Hour Trail Run. Winding across our Connecticut location, you’ll take in the beauty of the grounds and pass by iconic Camp buildings and program areas throughout the course.

Following the 5K, the “hole" gang is invited to a one-of-a-kind finish festival featuring refreshments and live music. Guests of registered participants are welcome. Register as an individual or share the Camp Challenge excitement by gathering your “gang” and creating a team! Teams of two or more can tackle the 5K or 6-Hour Trail Run together.

Want to make your trip to Camp even more memorable? Round up your friends and family and form a Cabin Circle team! Comprised of up to 10 members each, Cabin Circle teams commit to raising $2,500, a “campership,” supporting the costs of sending one child to Camp for a transformational week-long summer session. Your team will have the unique opportunity to spend Friday night, the night before Camp Challenge, AT CAMP! Sleep in the very same cabins where our campers have experienced many magical moments; enjoy a meal in the Dining Hall; gather around the evening campfires and celebrate with fellow members of Hole in the Wall’s community who help make “a different kind of healing” possible.

If you're interested in participating, or have any questions, please contact Jillian Roy at (410) 847-2954 or via email.

A Cabin Circle group poses behind a table of Challenge medals at the 2025 Camp Challenge

Camp Challenge

Saturday, May 17, 2025

A little bit of rain couldn’t dampen the enthusiasm of the 225 runners, walkers and spectators who gathered at The Hole in the Wall Gang Camp in Ashford, Conn., for this year’s Camp Challenge. Having rallied their communities to raise an inspiring $84,000 in support of Camp programs, they were now ready take on the Bandit 5K or 6-hour trail run! Camp pride was on full display, with teams such as Mischief Makers, Pond Loop Heroes and The Camped Crusaders mobilizing for a cause close to their hearts.

The festivities kicked off on the Friday evening before Camp Challenge, when 10 Cabin Circle teams arrived for an overnight experience filled with magical Camp moments-a special opportunity for teams who raised a minimum $2,500. Cabin Circle teams were comprised of former campers, current and former staff and volunteers, and families participating in memory of campers who have passed, as well as other long time and new Camp friends. All were treated to a pre-race buffet dinner and cozy bonfires with s’mores and snacks, sharing Camp camaraderie before the big event.

On Saturday morning, Camp was abuzz, as more spirited teams and individuals joined in on the fun! Waves of costumes representing Camp’s Unit Colors: blue, red, yellow, green, and purple-were on full display as participants warmed up and enjoyed breakfast treats in the Dining Hall! First up…amidst cheers and hype music, our 6-Hour Trail runners headed for the start line with the goal of completing as many laps as possible over the course of their run. Camper Riley then welcomed the 5K group, sharing her story, reminding participants of the impact of their philanthropy on not only her, but every child who gets to come to Camp. With full hearts, runners and walkers embarked on the Bandit 5K!

As each Trail runner and 5K participant crossed the finish line in downtown Camp, they were met with encouragement, congratulations and endless high-fives! Lunch, live music, medals and more elevated the festivities as finishers reveled in their accomplishments and the magic of Hole in the Wall!

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