Five Reasons Not to Miss The Great Cortland Pumpkinfest

USA Today's 10 Best Fall Festivals Returns to Cortland! Every October since 1996, Downtown Cortland has been transformed into a vibrant, outdoor fall festival when The Great Cortland Pumpkinfest arrives in Historic Courthouse Park. The two-day event has been one of the county's most highly-anticipated fall celebrations, a family-friendly experience that has become a favorite for locals and visitors alike.

The festival returns on Saturday, October 4, at 10am, and continues at 10am on Sunday, October 5.

If you're looking for a fun and memorable way to spend a fall weekend in Cortland County, your search has ended. Here are five top reasons why Cortland's Pumpkinfest is a can't-miss event.

Not only will everyone's favorite fall décor be displayed throughout the park, but you can also purchase your first pumpkin of the season to bring home with you! Dave's Veggies offers locally grown pumpkins in every color, shape and size!

If you're feeling creative, try your hand at the Pumpkin Decorating Contest! Individuals and groups are encouraged to channel their inner Van Gogh and decorate a pumpkin. Carve it, paint it, bedazzle it, then show it off in the pumpkin contest! With categories from funniest to spookiest (and age groups from kids to adults), there’s a place for everyone’s creation to shine.

Bring your masterpiece to the pumpkin decorating haybales in the center of Courthouse Park between 10:30am and 11:30am on Saturday, October 4th, as judging will take place at noon. Winners will be announced at 12:45pm. Don't forget to pick up your pumpkin by 3pm the following day to take home as a spooktacular keepsake.

Pumpkinfest just wouldn’t be the same without its beloved annual craft show and this year’s lineup is bigger and better than ever! Over 50 talented vendors and artists will fill the park with handmade treasures, from cozy holiday décor and one-of-a-kind jewelry to clothing, photography, woodcrafts, and so much more.

Sample handcrafted whiskey at Dragonfyre Distillery’s Dragon Wagon, watch live macramé demos from Maslin’s Guarden, and snag some hauntingly beautiful Halloween-themed jewelry from Beacon Peak. It’s the ultimate “shopportunity” to find something special and support local makers while you’re at it!

Live entertainment will be performed throughout both days of the festival featuring music for all tastes. From Country to Classic Rock, Bluegrass to Funk, you name it, Pumpkinfest has got it.

Saturday, Oct. 4th

• 12:00 PM - Nicholas Stark
• 1:30 PM - Ageless Jazz Band
• 3:15 PM - Yayle Hues
• 5:00 PM - Papa Muse
• 6:45 PM - Colleen Kattau and Jane Zell

Sunday, Oct. 5th

• 12:00 PM - Bradford Allen
• 1:45 PM - Windowshoppers
• 3:30 PM - Bob Keefe and the Surf Renegades

If you’re tummy gets to rumbling The Great Cortland Pumpkinfest has you covered. It wouldn’t be Pumpkinfest without a big bag of piping hot kettle corn from Lulu’s or a juicy Prime Rib Sammy from Deli Guys Catering, but that’s just the beginning.

New to the lineup this year, The Spud Shack is serving up hearty comfort food, while Caribbean Patty World brings a burst of island flavor to your fall festivities. And of course, no visit is complete without a stop at Anthony’s 19th Hole.

Save room for the sweet stuff, too, like Dave’s legendary caramel apples or an irresistible treat from Sinfully Sweet Café.

Need something to wash it all down? Those 21 and over can toast to the season at the Pumpkin Pub, where local favorites from award-winning local breweries; McGraw Box Brewing and Homer Hops. 

You can hear the happy screams echoing from clear across the park! The midway is where the real fun kicks in at Pumpkinfest. It’s loud, colorful, and smells like popcorn and fried dough, in all the best ways. Try your luck at the games, grab an elephant ear, and see how brave you really are on the rides.

Whether you’re in it for the thrill or just tagging along for the snacks, the midway is guaranteed to keep things interesting. It’s open until 8pm on October 4 and 5pm on October 5, so make sure you get your fill of fun before it’s gone!

Don't miss an unforgettable autumn weekend at The Great Cortland Pumpkinfest, where local flavor, family fun, and fall magic come together in the heart of downtown Cortland. If you have any questions while you’re there, stop by the Pumpkinfest Information Tent, located near the historic Courthouse stairs at the center of the festival. For schedules, updates, and more festive inspiration, visit the official website, cortlandpumpkinfest.org or follow along on Facebook to keep the Pumpkinfest spirit alive all season long.

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