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Events Calendar

Winterfest: "A Jay County Holiday Celebration"

Friday, November 20, 2020 - Saturday, 21 November 2020 

WinterFest 2020 is a multi-day holiday celebration in Jay County, Indiana. In 2020, celebration related events will be held on Friday, November 20th, Saturday, November 21st, Friday, December 4th, Saturday, December 5th, Sunday, December 6th and Friday, December 11th!

2020 WinterFest Schedule of Events:

Friday, November 20th -

Christmas @ The Courthouse (evening) 

** Sip N' Shop @ Jay County Merchants (afternoon/evening)

Saturday, November 21st -

Kids Breakfast & Carnival (purchase advanced tickets required; morning)

Lil' Miss WinterFest Pageant (afternoon)

Parade of Lights @ Downtown Portland (evening) and afterwards visit with Santa @ Courthouse (evening)

Friday, December 4th -

** Sip N' Shop @ Jay County Merchants (afternoon/evening)

Saturday, December 5th -

WinterFest 5k Run/Walk (morning)

** Sip N' Shop @ Jay County Merchants (afternoon/evening)

Visit Santa @ Fairgrounds (evening)

Sunday, December 6th -

Holiday Home Tours (12 pm to 5 pm)

Friday, December 11th -

WinterFest Ball @ Jay Events Center with Carriage Rides & Silent Auction (7 pm to 11 pm)

** A free copy of the complete list of Jay County Merchants participating in the Sip N’ Shop event can be obtained at the Chamber’s office and also accessed at their website located at

Save these dates and make WinterFest 2020 the start of your family’s holiday celebration and a season to remember. For information or event tickets, contact the Jay County Chamber of Commerce in Portland, Indiana. Phone: (260) 726-4481 or Email: This email address is being protected from spambots. You need JavaScript enabled to view it.



Location Various Locations Throughout Jay County

Contact Jay County County Chamber of Commerce @ 260-726-4481