Cortland County Events Calendar
Looking for things to do in Cortland County? This is the master list. Find festivals, live music, family fun, farmers markets, arts events, outdoor adventures, and the random fun stuff you only hear about if you know a local.
Annual Festivals Worth Planning Around
Some weekends in Cortland County are basically a tradition. These annual favorites bring the crowds (in a good way) with live music, food, classic small-town fun, and the kind of events you end up talking about all year.
Tip: Dates can shift a bit year to year. Check the listings below for this season’s details.
26th Annual Brockway Truck Show
Big rigs, local history and a crowd that truly appreciates a classic. Even if you don't know a Brockway from a box truck, it's a blast to see and hard to forget!
29th Annual Great Cortland Pumpkinfest
Fall in Cortland County comes with pumpkins, food, family fun and the official start of "yes, we're doing apple cider donuts again."
Homer Winterfest
Parades, winter fun and peak small-town magic, complete with the kind of community energy that makes you forget you ever complained about cold weather.
54 Annual CNY Maple Fest
Spring smells like maple here. Come for the syrup, stay for the vendors, demos, and the very real possibility you’ll buy “just one more” maple treat for the road.
Hosting an Event in Cortland?
Got a festival, show, fundraiser, class, community event, or something delightfully specific? Add it to the calendar so visitors (and locals who swear they “never hear about anything”) can find it.