09/08/2026
Today is a bittersweet day, and one I wasn’t always sure when—or if—would ever happen. After almost 12 years as the founder and owner of 33 Hilltop, a new chapter starts today.
It’s hard to put into words everything I want to say in this post, but first and foremost, I have to thank the community of Windham for accepting us with open arms since April of 2015. I grew up in Windham, and being supported by so many people who knew me as a young boy has always meant so much to me. Former teachers, coaches, family members of childhood friends—I always felt like Windham had our back. And with a perfect 12-0 record for Best Sandwich in Town, I think that speaks for itself!
When my brother-in-law Kyle and I opened Hilltop, we always wanted it to be a family restaurant, and it truly became one in every sense of the word. My mom, dad, sister, girlfriend, and two kids all put in countless hours helping the restaurant succeed, not to mention Kyle’s brother, dad, and niece all lending a hand in the early years.
But it didn’t stop with our families. In total, we had 24 families with multiple members employed at Hilltop at one time or another, including four families with three members and five members of the Squires/Page clan! There have even been two marriages—with a third on the way—and two kids who came from relationships that started between Hilltop employees.
And I can’t leave out the fact that Pittsburgh Steelers tight end Pat Freiermuth wore the Hilltop black and white long before he wore the black and yellow.
I want to thank all of our past and current employees for the hard work they put in over the last decade-plus. I wish I could thank everyone individually, but this post would become a novel, and I’d still probably manage to leave out a few Hilltop HOFers. The shop and I both had our share of ups and downs over the years, but the crew was always there to keep the ship afloat and help us get through them.
There are a few people I can’t go without thanking personally.
First, my parents, brother, and sister. They helped make me the person I am today and have always been role models I could look up to and aspire to be like.
My kids, Jackson and Aubrey, sacrificed so much in the early years while we were building Hilltop into what it became. They’ve been bussing tables and patrolling the counter since they were 3 and 1 years old. They are every bit as much a part of this restaurant as I was, and they supported me every step of the way.
My amazing girlfriend, Meg, came into my life during some of my darkest times, lifted me out of them, and has been beside me every step of the way through this sale. I can’t thank her enough for everything she has done for me.
And last but certainly not least, none of this would have happened without my brother-in-law Kyle. When he approached me about opening the shop together, I had never seriously thought about going back into the restaurant business or opening a place of my own. Without his experience, initiative, and confidence in the idea early on, I don’t know that I ever would have taken that leap of faith, left my job, and become my own boss.
I’m not sure exactly what the future holds from here, but I know I will always be grateful for my time with 33 Hilltop, the people I met along the way, the memories we made, and the community that supported us for all these years.
Thank you, Windham. Thank you to every employee who ever wore a Hilltop shirt, every customer who walked through our doors, and everyone who was part of this journey.
It’s been one hell of a ride.
