14th Annual Fly-In All You Can Eat Breakfast
2026-08-29 06:00 - 11:00 (America/Indiana/Indianapolis) | Portland Airport, 661 W 100 N, Portland, IN - Indiana, 47371
Stop out at our local airport for the breakfast and stay for a airplane ride.

Farmers Market
2026-08-29 08:00 - 12:00, 2026-09-05 08:00 - 12:00, 2026-09-12 08:00 - 12:00, 2026-09-19 08:00 - 12:00 | Jay Community Center, 115 E Water Street, Portland, Indiana, 47371

Book Sale
2026-08-29 08:00 - 12:00 | Jay County Public Library, 315 N Ship St, Portland, IN - Indiana, 47371
What new author will you find at the book sale!

Special Day for Special People
2026-09-03 16:00 - 20:00 | Jay County Fairgrounds, 806 E Votaw St, Portland, IN, 47371, United States
Sponsored by the Jay County Optimist Clubs. For our special people and their families.

Chainsaw Carving & Vendor Show
2026-09-11 09:00 - 2026-09-13 18:00 | Jay County Fairgrounds, 806 E. Votaw St., Portland, Indiana
Carvers from around the country, local vendors, food trucks, free movie on Friday night, the band Outlaw Nation will be performing Saturday and this years auction will benefit YSB of Portland.

Fall Festival
2026-09-12 10:00 - 18:00 | Wheel & Spoke Antique Mall, 500 S Meridian St, Portland, Indiana, 47371
Packed with cozy charm, guest vendors, aisles of vintage and treasures, home decor, seasonal shopping fun to kick off those fall vibes!

Harness Racing
2026-09-12 11:00 - 15:00 | Jay County Fairgrounds, 806 E Votaw St, Portland, IN, 47371, United States

Dunkirk Kiwanis Golf Scramble For Kids
2026-09-12 11:00 - 17:00
Proceeds help Riley Children’s Hospital

Jay County Cancer Society Car Show
2026-09-12 16:00 - 19:00 | Jay County Fairgrounds, 806 E Votaw St, Portland, IN, 47371, United States
2nd Annual Car Show!

Cancer Cruise-In & Carnival
2026-09-12 16:00 - 19:00 | Jay County Fairgrounds, 806 E Votaw St, Portland, IN, 47371, United States
Celebration of courage! Cruise-In 4pm-6pm, Carnival 5pm-7pm

Bonnie & Clyde Car Show
2026-09-13 08:00 - 17:00 | Jinny’s Cafe, Bryant, Indiana
Registration starts at 8:00am more information contact (260) 409-5368

Jay County Bridge Dinner
2026-09-17 17:30 - 20:30
An opportunity for the community to come together for food, music and a chance to visit with friends and family. Located at the green bridge going into Hudson Park.

Military Vehicle Show
2026-09-18 00:00 - 2026-09-19 23:59 | Jay County Fairgrounds, 806 E Votaw St, Portland, IN, 47371, United States
Vehicles & guns from various wars.

Brianna's Ride For Recovery
2026-09-26 10:00 - 17:00 | Hudson Family Park, 509 S Wayne Street, Portland
You don’t have to ride a motorcycle to be part of the celebration—everyone is invited! Come enjoy great music, great food, and an unforgettable afternoon of hope.

Jay County Heritage Festival
2026-09-26 11:00 - 2026-09-27 16:00 | Jay County Historical Society Grounds, 903 E. Main St., Portland
Demonstrations, food, crafts, entertainment and exhibits, this years theme is America 250!

Pennville Pumpkin Festival
2026-10-17 10:00 - 16:00 | Pennville Park, Pennville
Pumpkin contest, parade, arts and craft vendors fun family event!

JayCon Tabletop Gaming Convention
2026-11-06 08:00 - 2026-11-08 17:00 | Wheel & Spoke Event Center, 555 S Bridge St, Portland, IN - Indiana, 47371
Join us for this FIRST ever event, get your tickets to come and play games such as Dungeons & Dragons, Pokemon, Magic the gathering, and more.

Delts' Holiday Crafts & Gifts Show
2026-11-14 09:00 - 15:00 | Jay County High School, 2072 West St. Rd 67, Portland
41st Annual event, over 150 booths.

Midnight Gladness
2026-11-21 10:00 - 23:30 | Wheel & Spoke Antique Mall, 500 S Meridian St, Portland, Indiana, 47371
Lights are twinkling throughout the mall. Get into the holiday spirit with night shopping extravaganza!

Jay County Farm Toy Show
2026-12-13 08:30 - 14:30 | 4-H Building, Jay County Fairgrounds, 806 E. Votaw St., Portland
Browse through 70+ tables of new and used farm toys and a few related crafts.
