Windsor Fair

Windsor Fair Maine's 2nd largest agricultural fair, in Windsor, Maine Aug. 23rd - Sep. 1st, 2025, 9AM - 10PM / Mon., Sep. 1st, 9AM - 6PM. Parking Free. No Glass
No Weapons

Maine's 2nd Largest Agricultural Fair
Sat 8/29/26 - Mon 9/7/26 Open at 9am each day
https://windsorfair.com/tickets/
Giant Midway, Harness Racing, Demo Derbies, Truck, Tractor & Livestock Pulls, Live Music, Historical Museum, Exhibition Hall Admission: $15 Ages 12 and up / Ages 11 and under Free. No Pets are allowed on the fairgrounds during the fair. Only fully trained service animals and Police

K-9s are allowed. Per Maine and Federal law, emotional support, comfort and companionship animals do not qualify.

*Attention Harness Racing Fans* Monday's printed harness racing program has a typo. It lists the post time as 3pm, the c...
08/30/2026

*Attention Harness Racing Fans* Monday's printed harness racing program has a typo. It lists the post time as 3pm, the correct post time on Monday is 2pm.
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Sheriff N scores his 55th career win at the Windsor Fair

Windsor, Maine ... Like the fabled old gunslingers of our old west legends, Sheriff N bravely held his ground and took no prisoners while coldly staring down his foes on Saturday (August 29), securing his 55th score of his veteran career while keeping the peace in a crowded rush to the finish line during the opening session of harness racing at the Windsor Fair.

Ably guided by owner/trainer Zachary Vickerson, Sheriff N fought bravely for the early lead, insisting on the top spot through a bit of give-and go to the opening quarter. From that point on, the raceway belonged to the 12-year-old son of Bettor’s Delight as Vickerson expertly placed his competition across the raceway, steadfastly refusing to give way, while leveraging each challenge to his best advantage.

Rounding the final bend, a gang of three launched one final assault against Sheriff N as the field careened toward the fast approaching wire. But Sheriff N confidently held his ground, holding off the late, desperate cavalry charge at the wire, ultimately surviving a four horse photo over Duncan’s Ranger (Todd Whitney), Cntnobdytelmenothn (Derek Howes), and Monaco Hanover (Michael Girouard) to seal the 1/4-length deal timed in 1:58.4.

“Oh yeah, I knew he could get it done here today” Vickerson’s partner, Haley Farken remarked in a winners circle interview, “He likes this track, this surface, he’s win here a couple of years for us. I mean, I hammered him to win!”

“He’s a good, old, classy horse. We’ve had him three years now and he just always gets it done for us.”

Sheriff N who was sent to the gate at 7-1 odds, returned a generous $16.40 to win and began a trend toward price play winners throughout the mid-portion of the Windsor Fair Card as seven of the twelve races resulted in win payoffs in the double digit range. Joining the long-shot barrage were West River Jordan and Ron Cushing at 10-1 ($22.40), Century Liberty and Andy Harrington at 8-1 ($19.20), Gabe Hanover and Joey Mosher at 9-2 ($11.60), Profit Blue Chip and James Doucette at 5-1 ($12.60), Hide The Wick and Joey Mosher at 15-1 ($32.40), and Wolftrax with Ron Cushing at 15-1 ($32,20).

The opportunity for more long-shot plays continues when harness racing resumes at the Windsor Fair on Sunday (August 30) with post time scheduled for 1:00 pm (EDT). The eleven-race betting card will be preceded by two non-wagering Maine Sire Stakes event scheduled for 12:30 pm.

As is the norm, harness racing will be the featured afternoon attraction at Windsor throughout the 10-day late-summer agricultural exhibition. Saturday and Sunday post times are set for 1:00 pm (EDT), weekday posts (with the exception of the dark Wednesday on September 2) slated for 2:00 pm, while the traditional Labor Day program provides the grand finale beginning at 1:00 pm.

Senior citizens (60+) will be afforded $5 admission to the fair on Monday (August 31) and again on Thursday (September 3) while veterans will received free admission on Thursday (September 3) with military ID.

For the complete harness racing schedule at the Windsor Fair, please visit www.windsorfair.com/events/harness-racing/

The live video feed of all the harness racing action at Windsor Fair can be enjoyed online at www.youtube.com/ , programs may be found at www.trackmaster.com , while wagering for the races at Windsor will be available both on track and online on the Hollywood Races site at www.hollywoodraces.com

Photo by Joe Shaw - Sheriff N holds a bevy of challengers at bay to secure his 55th career win.
Please contact Mike Sweeney (207-252-8873) for further info.

Hollywood Races is an online horse betting site. Bet online, on our app, by phone or at the track. View live races, replays, results, schedules and more.

Here's our entertainment lineup for the next 4 days and our program for Mon-Thurs.  Monday Woodsman's day events, 3 nigh...
08/30/2026

Here's our entertainment lineup for the next 4 days and our program for Mon-Thurs. Monday Woodsman's day events, 3 nights of Truck & Tractor Pulls, Weds night Farmer Olympics 7pm, Thurs Veteran's Ceremony and Demo Derby #2
See you at the fair!
Buy your tickets online and skip
https://windsorfair.com/tickets/

King Arthur baking contest. Judges tasting and scoring each dish.This year the adults made "Applesauce Oatmeal Bread" an...
08/30/2026

King Arthur baking contest. Judges tasting and scoring each dish.
This year the adults made "Applesauce Oatmeal Bread" and the youth made "Apple Cider Snickerdoodles"
Announcement of winners to follow in a while.

🚗🚨Demo Derby  #1 is tonight at 7pm, included with gate admission.  Up for auction will be 5 demo derby cars! Bring your ...
08/30/2026

🚗🚨Demo Derby #1 is tonight at 7pm, included with gate admission. Up for auction will be 5 demo derby cars! Bring your $ and your helmet and bid high and bid often and get yourself into the action! It's an experience of a lifetime, no doubt. New this year, Matt James will be our guest emcee for the derby. The only extra charge is $5 for a bracelet if you want to watch from the infield. We by all accounts expect that the show will go on tonight as heavy extended rain is not expected. A little rain will just keep the flames in check! 🔥🚒

This morning some of our amazing volunteers spent their early morning starting at 5:15am doing live interviews to promot...
08/30/2026

This morning some of our amazing volunteers spent their early morning starting at 5:15am doing live interviews to promote our fair, and our mission of supporting agriculture & agricultural education. Thanks go out to -TV channel 8 for the great press this morning.

Harness Racing every afternoon, except Weds. Come watch the horses fly! 🏇🐎
08/30/2026

Harness Racing every afternoon, except Weds. Come watch the horses fly! 🏇🐎

THE SCORE IS THE PLACE FOR LOCAL SPORTS!!!

Today.., it's live coverage of the thrills and excitement of harness racing from the 138th Windsor Fair! Mike Violette hosts our coverage with a 1 o'clock post time. Hear the races over the radio on The Score, Sports Radio 1160 WSKW and online at 1160thescore.com and the websites of our sisters mixmaine.com, truecountry935.com and wkitfm.com.

Address

82 Ridge Road
Windsor, ME
04363

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