
Main Street’s Secrets Unlocked

Step into the heart of downtown Cortland and discover the stories hidden in plain sight. On this captivating walking tour, City Historian Kate O’Connell will lead you through the business district’s storied streets, peeling back the layers of history to reveal tales of ambition, scandal, and resilience. From architectural marvels to the unforgettable characters who built (and sometimes broke) this city, you’ll see Main Street as you’ve never seen it before.
Along the way, Kate will share the surprising histories behind familiar facades, the triumphs and tragedies etched into stone, and the long-forgotten events that shaped Cortland’s destiny. This is more than a stroll. It’s a step into another time.
Tours begin at 2 North Main Street (Bailey Place Insurance) at 9:30 a.m. Rain or shine, wear comfortable shoes and prepare to be transported. The journey lasts about 1.5 to 2 hours, leaving you perfectly placed to enjoy lunch at one of downtown’s eateries.
Dates: September 20 and October 4
Donation: $10 per person, benefiting the Cortland County Historical Society
Reserve your spot: Call 607-756-6071 or email info@cortlandhistory.org.
History is waiting. Will you answer?