Highland Woods is home to many accomplished professionals, and among them is Despina Karas, a proud resident and accomplished restaurant owner who has lived in the community since 2014. Despina is co-owner of The Village Squire locations in South Elgin, West Dundee, as well as Rookies in Huntley and Crystal Lake.

The Karas family legacy spans over five decades and represents a true Greek-American success story. What began with two brothers and one small tavern in suburban Chicago has grown into a beloved local enterprise employing hundreds and serving thousands of loyal patrons. The story began in 1974 when Despina’s father, Paul Karas, purchased The Village Squire in West Dundee. After arriving in Elgin with just $25 in his pocket and working a variety of jobs—including at the Elgin Watch Factory and the State Street Market—his entrepreneurial spirit led him to open a downtown Elgin bar. His brother George joined him in 1971 from Krinides, Greece, and together they expanded the business with relentless determination.

Having grown up in the restaurant industry, Despina always envisioned a career in hospitality. Her love for food and community made this a natural fit for her. She shares, "Our restaurants are special because they are extensions of our homes and ourselves. It’s our own concept and creation, and it’s very dear to us that it’s ours."

For Despina, running the restaurants is not just a business—it’s personal. That personal connection is deeply rooted in her upbringing. As the child of Greek immigrants, she often served as a translator for her parents and extended family. The family's strong ties to the local Greek community helped found St. Sophia Greek Orthodox Church in Elgin, which continues to be a central part of their lives.

A value that guides Despina is philoxenia —a Greek word meaning "friend of the stranger." It encapsulates her approach to hospitality: welcoming every guest like family. This spirit also extends to community involvement. The restaurant is known for supporting local organizations, including churches, youth sports leagues, shelters, and the Boys and Girls Club. "We never say no to a gift card donation," Despina says. "If someone asks, we just ask how many. We’ve never turned one down."

Today, Despina’s brother and co-owner, Bob Karas owns the Karas Restaurant Group, which includes Alexander’s Café in St. Charles and Elgin, Old Republic, The Squire on the Square in Woodstock, several Rookies Sports Bar locations, and the newest location in Campton Hills, Squire Ale House. Visit Despina at The Village Squire in South Elgin, where you will likely find her preparing food, serving guests, and talking with regulars. 

For Despina Karas, Highland Woods is more than just home. It’s where she lives out the values passed down through generations—hard work, hospitality, and community connection—all while serving up great meals in places that feel like home to so many.