About Us – Our Story
Big O’s on the Hollow began with a dream, a hardworking team, and a love for bringing people together through food. In early 2018, Kevin O’Brien and his parents, Patrick and Doreen, purchased the restaurant to create something unique for Freeport. From the very beginning, we wanted to be more than just another dining spot — we wanted to be a place where people felt like family.
Our early years weren’t easy. Opening a restaurant comes with plenty of challenges, and we experienced our share, including navigating the difficulties of the pandemic. But with the help of our loyal customers, a dedicated staff, and the unwavering support of our community, we kept pushing forward. Today, Big O’s has grown into a local favorite, consistently recognized as one of the region’s best places for classic American food, friendly service, and good times.
Growing with Our Community
We’re proud of how far we’ve come since opening our doors. Over the years, we’ve reinvested back into the business to enhance the experience for our guests, with remodeling the dining room, kitchen, and bathrooms and ensuring everything is modern, welcoming, and comfortable.
We’ve also worked alongside local organizations such as the Greater Freeport Partnership, Friends Forever Humane Society, and the Children’s Hands-On Museum of Northwest Illinois. Whether it’s participating in community drives, hosting events like Cupcakes & Cocktails, or contributing to groups like 100 Men Who Care, we believe in supporting the people and places that support us.
A Local Freeport Favorite
Our restaurant sits right on Illinois Route 75, just off Route 20, making us easy to find for both locals and travelers passing through on their way between Rockford and Galena. While we love welcoming visitors, most of our guests come from right here in Freeport and the surrounding Stephenson County area.
Many of our regulars stop in multiple times a week because they know they’ll always find a welcoming atmosphere, great service, and a menu full of their favorites.
What We Serve
At Big O’s on the Hollow, our focus is on hearty, flavorful, American-style meals that keep people coming back. Our menu includes:
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- Flame-Grilled Burgers: Fresh, juicy, and customizable.
- Hand-Cut Ribeye Steaks: Cooked to perfection and known as some of the best in the area.
- House-Smoked Brisket: A customer favorite, especially when paired with our beer cheese mac.
- Weekly Specials: Including pork chops, tenderloins, tacos, wings, and smoked prime rib.
- Fun & Unique Dishes: From alligator and duck strips to creative wraps and sandwiches.
- Famous Friday Fish Fry: Our biggest tradition, featuring six kinds of fish prepared pan-seared or deep-fried.
We also offer appetizers, fresh salads, sandwiches, and entrees like smothered chicken and lemon pepper shrimp, ensuring there’s something for everyone.
A Place for More Than Dining
Our restaurant isn’t just about food — it’s about experiences. With seating for 20–22 tables in our main dining room, plus an expanded dining area and deck, we can comfortably accommodate large groups. Our private event space is perfect for baby showers, birthday parties, rehearsal dinners, and even weddings of up to 140 people.
The Tradition of Volleyball
One of the features that makes Big O’s unique is our volleyball courts. Volleyball has been a tradition here for more than 20 years, and we’ve embraced it wholeheartedly. We’ve invested heavily to create courts that are professional-grade, with perfectly leveled sand and durable fencing. Summer leagues bring together teams from across the community, making Big O’s not just a restaurant, but also a hub for recreation and connection.
Looking Ahead
As we continue to grow, our goals remain simple: to keep improving, to continue investing in our business and community, and to always provide a place where people can gather, eat, and celebrate. Freeport has been incredibly supportive of us since day one, and we’re proud to be part of this community.
Whether you’re here for a casual dinner, joining a volleyball league, planning a private event, or simply stopping in for our Friday Fish Fry, our mission is the same: to make every experience at Big O’s on the Hollow one to remember.
A Local Spot You Can Count On
At Big O’s on the Hollow, we’re proud to be a family-run restaurant that reflects the values of our community, and we’ve worked hard to create a space where neighbors can gather, enjoy quality meals, and celebrate milestones big and small. What started as a dream has grown into a Freeport tradition, built on the support of loyal customers and the passion of a dedicated team. So if you’re looking for a place that combines delicious food, friendly service, and a commitment to community, we invite you to join us at Big O’s on the Hollow. We’re here to serve, to celebrate, and to keep Freeport’s dining scene thriving — one meal at a time.