Entertainment

Enjoy 6 days of local and national talent on the stages throughout the fairgrounds.

2025 Entertainment – Columbia County Fair

  • Demolition Derby – Friday

    Friday, August 29, 6:30PM

    Location: GRANDSTAND

    The Demolition Derby Finale: Watch 6 and 8 cylinders and full-size pick-ups and vans crash hard on Friday night for the cash purse of $1,500. Best Appearance Theme: Monster Trucks

    Sponsored by Madsen Overhead Doors & Sorros Excavating LLC

  • Monster Tractor Pull

    Saturday, August 30, 4PM

    Location: GRANDSTAND

    What started out many years ago with farmers bringing their favorite tractors out of the fields to the local fair and pulling the heaviest stone boat the furthest has progressed into the HEAVIEST MOTOR SPORT IN THE WORLD! Watch these modified, Super Stock and Super Farm class tractors and 4 wheel drive trucks roar past the Grandstand in hopes of a full pull, bragging rights and points towards the circuit championship!

    Sponsored by A. Colarusso & Son

  • Firefighters’ Parade

    Saturday, August 30, 11 AM

    Location: NORTH GATE ENTERTAINMENT BARN

    More than 40 units from five counties will lineup for the Columbia County Fair’s 72nd annual Firefighters Parade on Saturday, August 30, stepping off at 11 am from the corner of Kinderhook Street and Woodbridge Avenue in the Village of Chatham. Viewing and judging of the parade will take place near the North Gate entrance of the fairgrounds off Route 203. Judging will take place by the Hudson Valley Judging Association with awards handed out at the conclusion of the parade.

    Sponsored by A. Colarusso & Son

  • DJ Jack Bogarski

    Thursday, Sept. 3 & Friday, Sept. 4: 6PM; Saturday, Sept. 5: 11AM-5PM

    Location: PAVILION

    DJ Jack Bogarski returns to the Columbia County Fair Beer Pavilion for his 29th consecutive year this 2026 season. Jack will be providing musical entertainment Thursday and Friday night (9/3 & 9/4) from 6pm till close for the 21+ crowd, and on Saturday from 11am-5pm for the parading Firefighters and fairgoers. “Playing the right song at the right time.” Come join us.

  • Electric Blue DJ Bob Hawley

    North Gate: Aug 27, 9PM; Beer Pavilion: Aug 30 & 31, 6PM and Sept 1, 2PM

    Location: NORTH GATE ENTERTAINMENT BARN & PAVILION

    Electric Blue DJ Service has been providing Rock, Classical, Jazz, Country, Rap, and Hip-Hop music for 30 years, originally starting out as DJ at the Skate Factory near Hudson.

  • Heritage Building

    Wednesday, Aug. 27 - Monday, Sept. 1 (continuous)

    Location: NORTH END

    Candle making, wood carving, rug hooking, fly tying, jewelry making, tin smithing, iron work, all handcrafts that have been superseded by mechanization. Here in Heritage Village, see craftspeople working the old fashioned way – with their hands. Get a chance to not only watch something being made, but, if you choose, purchase an object to take home – a hand-crafted keepsake.

Such a great Fair every year. This year 2021 was my First year back since I was in elementary school which was decades back. You all worked so hard and did a wonderful job I’ll continue coming back every year.

– Jonathan B.

Love It! Nice country Fair.

– Theresa C.

Definitely the best county fair I have ever been to! The tree-lined grounds are lovely. A nice mix of attractions and exhibits with phenomenal entertainment; well worth the price of admission.

– Linda A.