Most people in Crystal Lake know the Dole Mansion. Some know it as the home of Lakeside Fest. Others visit for the Farmers Market+, art events, classes, or community gatherings. Many have admired the stately mansion from across the lawn, framed by towering oak trees and overlooking the lake that gave Crystal Lake its name.
What many may not realize is just how many lives the property has lived. Or how closely its future has become tied to one beloved summer tradition.
Built in 1865 by grain baron and ice harvester Charles Sydney Dole, the mansion began as an elegant summer estate on the shores of Crystal Lake. At a time when harvesting lake ice was a thriving industry, the Dole family helped shape the early identity of the growing community.
As industries changed and the Dole family moved on, the property entered a new chapter. In 1922, Eliza "Lou" Ringling, widow of circus magnate Al Ringling, purchased the mansion and surrounding acreage. A visionary businesswoman, Lou transformed the estate into the Crystal Lake Country Club, adding guest rooms, a ballroom, golf courses, riding stables, and other amenities that made the property a destination for recreation and social life.
Over the decades, the property changed hands several times. It served as a school, a seminary, and eventually became home to First Congregational Church. By the late 1970s, the church was operating Friendship House, a nonprofit childcare center serving local families, from the property and working to maintain the aging estate.
It was during that period that a simple idea took root.
For nearly five decades, Lakeside Fest has been a summertime tradition in Crystal Lake, but its roots are surprisingly modest. What began in 1979 as a small ice cream social hosted by First Congregational Church on the grounds of the Dole Mansion was simply a way to bring people together and support the upkeep of the historic property.
There were no carnival rides. No concert stages. No beer tents.
"It was an ice cream social. Very small. Hundreds of people, not thousands. No bands or alcohol, and no food other than ice cream," recalled longtime organizers, and current Dole Board Members, Ron Russell and Chip Whitman.
The gathering reflected the church's mission at the time. Families connected through Friendship House, church members, and neighbors came together on the lawn overlooking Crystal Lake.
"FCC owned the property at the time and operated Friendship House," they said. "There were many families that sent their kids, and it was a nice gathering of parents and churchgoers."
Nobody involved was trying to build a major festival.
"They really were not thinking about a large festival initially," Ron and Chip said.
The event was simple. Volunteers set up folding tables. Families spread out blankets beneath the trees. Children played on the lawn while neighbors caught up with one another. It felt less like a festival and more like a community picnic.
Yet year after year, people kept coming.
The ice cream social gradually grew. More activities were added. Attendance increased. What started as a church fundraiser slowly evolved into something larger, though it never lost its community-centered roots.
As the festival grew, so did the challenges facing the Dole Mansion.
Maintaining a historic property is expensive, and the future of the estate was not always certain. The turning point came in the early 2000s when the property faced possible redevelopment. Community members rallied to save the mansion, forming what would become the Lakeside Legacy Foundation.
Suddenly, Lakeside Fest represented something more than a summer tradition. It had become part of the effort to preserve one of Crystal Lake's most important historic landmarks. Today, the connection between the festival and the Dole is stronger than ever.
The Dole now operates as a 501(c)(3) nonprofit organization and has evolved into a recognized cultural arts hub and community center serving Crystal Lake and the surrounding region. Revenue generated through Lakeside Fest helps support preservation efforts, programming, and ongoing improvements throughout the property.
What was once a struggling historic estate has become a vibrant community destination.
Recent restoration projects have brought the mansion's second floor back to life, preserving important pieces of the building's history while making them accessible for future generations. Another notable addition is Lou's Lounge, a stylish gathering space named in honor of Eliza "Lou" Ringling. Located within a portion of the former country club addition, the space pays tribute to the property's colorful past while creating a new place for people to gather and connect. A full bar, small bites, and live music offer a swanky nod to the glittery past.
For Dole Board President Jay LeCoque, that balance between preservation and community use is essential.
"Preservation and relevance are not competing goals, they strengthen each other. We have a responsibility to protect the Dole Mansion and its history, but we also have a responsibility to ensure the property remains active, accessible, and meaningful to today's community," he said.
Today, the Dole is home to artist studios, galleries, classes, community events, nonprofit partnerships, and cultural programming that serves thousands of people throughout the year. Yet the mission remains remarkably similar to the one that inspired the first ice cream social decades ago: bringing people together.
Lakeside Fest continues to be the organization's largest annual fundraiser and its most visible expression of that mission.
This year, thousands of visitors will once again gather on the same lawn where church families once shared ice cream beneath the trees. There will be live music, carnival rides, food vendors, family activities, and plenty of opportunities to reconnect with friends and neighbors.
Most attendees will come for a good time.
What they may not realize is that every ticket purchased, every wristband sold, and every visit to the festival helps support something much bigger.
It helps preserve a 160-year-old landmark. It helps fund arts and cultural programming. It helps maintain a community gathering place that has served Crystal Lake in one form or another for generations.
And it ensures that the story of the Dole Mansion continues.
If the walls of the Dole could talk, they would tell stories of grand summer parties, country club dances, church gatherings, community meetings, artists at work, and families making memories on the lawn.
For nearly fifty years, Lakeside Fest has become part of that story.
What began with a few hundred people sharing ice cream on a summer afternoon has grown into one of McHenry County's signature events. More importantly, it has helped ensure that one of Crystal Lake's most treasured places remains alive, active, and welcoming for generations to come.
For nearly five decades, Lakeside Fest has been a summertime tradition in Crystal Lake, but its roots are surprisingly modest.
It was an ice cream social. Very small. Hundreds of people, not thousands. No bands or alcohol, and no food other than ice cream."