Fun Is Just Around the Corner at the Windsor Fair

Schedule of Events:

August 23, 2025

"Get Acquainted Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time at 1:00 P.M.
Giant Midway Opens at 12:00 P.M. – 10:00 P.M.
9:00 A.M. Maine Association Barrell Horse Racing (Lincoln Orff Show Ring)
9:00 A.M. Giant Pumpkin/Squash Contest – Registration & Weigh in (Ag. Tent)
9:15 A.M. All Day Ancient Ones of Maine Living History (Windsor Historical Society)
9:30 A.M. Steer & Oxen Scooting Contest, Dept. 6 (Vanner Pulling Ring)
10:00 A.M. Poultry Show (Poultry Building)
10:00 A.M. 3rd Annual Children’s Checker Contest (Exhibition Hall)
11:00-8:00 P.M. Beano at the Beano Hall
12:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
7:30-9:00 P.M. Runnin’ Down A Dream – Tom Petty Tribute Band (Grandstand)

August 24, 2025

"Museum Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time 1:00 P.M.
Giant Midway Opens at 12:00 P.M. – 10:00 P.M.
9:00 A.M. Show Steer & Oxen Percentage Farmer’s Pull 1901 & over, Dept. 4, Class N (Vanner Pulling Arena)
9:15 A.M. All Day Ancient Ones of Maine–Living History (Windsor Historical Society)
9:30 A.M. Draft Horse & Draft Pony Show (Lincoln Orff Show Ring)
10:00 A.M. The Maine Classic Open Boer Goat Show
followed by Youth Boer Goat Show (Prime Show Barn)
11:00-8:00 P.M. Beano at the Beano Hall
12:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
2:00 P.M. King Arthur Baking Contest Judging (Youth and Adults), (Exhibition Hall)
3:00 P.M. Manure Toss Contest (Vanner Pulling Ring)
5:00 P.M. Maine Junior Holstein Show (Prime Show Barn)
7:00 P.M. Demolition Derby #1 – Sign up at Gate 5 at 4:00P.M. ($20.00 Entry Fee)
Sponsored by "Paul’s Pick-A-Part" of Chelsea, Maine

August 25, 2025

"29th Annual Woodsman’s Day"

Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 - Seniors (60+) $5.00, (11 and under free)
Harness Horse Racing – Post Time 3:00 P.M.
Giant Midway Opens at 3:00 P.M. – 10:00 P.M.
9:00 A.M. Maine State Holstein Show - (Prime Show Barn)
9:30 A.M. Woodsman’s Field Day Events (Vanner Pulling Arena)
9:30 A.M. Show Steer & Oxen Wood Twitching Contest, Dept. 4, Class J (Lincoln Orff Show Ring)
11:00-8:00 P.M. Beano at the Beano Hall
12:30 P.M. Maine State Jr. Holstein Pee Wee Showmanship (Prime Show Barn)
1:00 P.M. Show Steer & Oxen Wood Twitching Contest, Dept 4, Class J (Lincoln Orff Show Ring)
3:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
6:30 P.M. Maine State Truck & Tractor Pulls: Local pullers ½ ton, ¾ ton & 1 ton; Mini Modified Tractors: 7300lbs
Street Gas PU MSTTPA 7300 lbs. Pro Street Gas PU MSTTPA - (Racetrack – Infield) 

August 26, 2025

"Horsemen’s Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time 3:00 P.M.
Giant Midway Opens at 3:00 P.M. – 10:00 P.M.
9:15 A.M. Show Steer & Oxen Percentage Farmer’s Pull 1900 & Under, Dept. 4, Class M (Vanner
Pulling Arena)
11:00-8:00 P.M. Beano at the Beano Hall
1:00 P.M. Show Steer & Oxen Wood Scotting Contest 1901 & Over, Dept. 4, Class K (Lincoln Orff
Show Ring)
2:30 P.M. Garden Tractor Pulls (Vanner Pulling Arena)
3:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
5:30 P.M. Cooking Contest Judging (Beef Stew), (Exhibition Hall)
6:00 P.M. Pig Scramble – 8-year-olds (Vanner Pulling Arena)
Must enter before 5:45 P.M. at the Information Booth – 12 Entries will be drawn
6:30 P.M. Maine State Truck & Tractor Pulls: Stock Farm Tractors: 10,500lbs, 12,500lbs, 14,500lbs, 16,500lbs; Lt
Pro Farm Tractors, Hvy Pro Farm Tractors – (Racetrack – Infield)

August 27, 2025

"Vendor Appreciation Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 (11 and under free)
NO HORSE RACING
Giant Midway Opens at 3:00 P.M. – 10:00 P.M.
9:15 A.M. Show Steer & Oxen Percentage Farmer’s Pull 1901 & over, Dept. 4, Class N (Lincoln Orff
Show Ring)
9:30 P.M. Farmers Horse Twitching, Scooting (Vanner Pulling Arena)
Kids Class Twitching to Follow
9:30 A.M. Judging of Show Sheep (Prime Show Barn)
11:00 A.M. Farmers Scooting Contest (Vanner Pulling Arena)
11:00 A.M. Decorated Pumpkin Contest Judging (Exhibition Hall)
11:00 A.M. Scarecrow Contest Judging (Exhibition Hall)
11:00-8:00 P.M. Beano at the Beano Hall
1:00 P.M. Show Steer & Oxen Wood Scooting Contest 1900 & under, Dept. 4, Class L (Lincoln Orff Show Ring)
1:30 P.M. Farmers Log Hauling (Vanner Pulling Arena)
1:00-5:00 P.M. Accepting Apple Pies & Registration (Rt. 32 Roadhouse)
3:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
6:00 P.M. Maine 2 Crusted Apple Pie Contest (Rt. 32 Roadhouse)
6:00 P.M. Pig Scramble – 9-year-olds (Vanner Pulling Arena)
Must enter before 5:45 P.M. at the Information Booth – 12 Entries will be drawn
6:30 P.M. Maine State Truck & Tractor Pulls: 2.5 Street Diesel PU, 3.0 Pro Stock Diesel PU, 2x4 Super Stock PU,
4x4 Super Stock PU (Racetrack – Infield)
7:00 P.M. Farmer’s 20 Ft Short Pull (Vanner Pulling Arena)
7:00 P.M. Farmer’s Olympics, ages 17 and up (Prime Show Barn)

August 28, 2025

"Senior Citizens" & "Veterans Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 - Seniors (60+) $5.00 (11 and under free) (Veterans with ID get in free)
Harness Horse Racing – Post Time 3:00 P.M.
Giant Midway Opens at 3:00 P.M. – 10:00 P.M.
9:15 A.M. Steer Pulling – 16 yrs old & Under, Steer Under 1300 lbs. (Vanner Pulling Arena)
Open Pulling – 1700 lbs. & Under, 2100 lbs. & Under, 2500 lbs. & Under,
2900 lbs. & Under, 3300 lbs. & Under
9:30 A.M. Judging Dairy Cattle (Prime Show Barn)
10:00 A.M. Veterans Day Ceremony (Entertainment Area)
11:00-8:00 P.M. Beano at the Beano Hall
11:30 A.M. Sheepdog Demonstrations (Lincoln Orff Show Ring)
1:00 P.M. Oxen – 3700 & under – Merle Vanner Memorial Trophy 4100 & under – If no 2 legitimate teams in the class,
they will pull in the 3700 with added weight and adjustments of premiums.
Sweepstakes distance pull (Vanner Pulling Arena)
2:00 P.M. Sheepdog Demonstrations (Lincoln Orff Show Ring)
3:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
5:30 P.M. Baking Contest - Judging (Cheesecake) (Exhibition Hall)
6:00 P.M. Windsor Fair Apple Queen Contest (Entertainment Area)
7:00 P.M. Oxen 6 FT. Pull – 3300 lbs. over & under class – Merle Vanner Memorial Trophy (Vanner Pulling Arena)
7:00 P.M. Demolition Derby #2 – (Racetrack Infield) – (Signup at Gate #5 at 4:00 P.M. - $20.00 Entry Fee) -
Sponsored by "Paul’s Pick-A-Part" of Chelsea, Maine

August 29, 2025

"Livestock Appreciation Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time 3:00 P.M.
Giant Midway Opens at 3:00 P.M. – 10:00 P.M.
9:15 A.M. New England Jumpers Association Horse Show (Lincoln Orff Show Ring)
9:30 A.M. Judging of Beef Cattle (Prime Show Barn)
11:00 A.M. Horse Pulling – 2 lb. Rock, Open to any weight (Vanner Pulling Arena)
11:00-8:00 P.M. Beano at the Beano Hall
1:00 P.M. Horse Pulling – 3000 lb. & Under Distance Pull (Vanner Pulling Arena)
3:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
6:00 P.M. Horse Pulling – 3000 lb. & Under 12FT. Pull (Vanner Pulling Arena)
"John Kelley Memorial Pull"
Sponsored by Twins Market of Augusta, Maine
6:30 P.M. Youth Sheep Obstacle Course (Prime Show Barn)
7:30 P.M. Peter Allen & Hurricane Mountain Band (Grandstand)
Giant Fireworks to follow

August 30, 2025

"Youth Livestock Show Day"
Gates Open 9:00 A.M.
Gate Admission:12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time 1:00 P.M.
Giant Midway Opens at 12:00 P.M. – 10:00 P.M.
9:15 A.M. Youth Dairy Show (Prime Show Barn)
9:15 A.M. Youth Rabbit Show (Gate 4, Barton Barn)
9:15 A.M. All Day Ancient Ones of Maine Living History (Windsor Historical Society)
10:00 A.M. Youth Working Steer (Lincoln Orff Show Ring)
10:30 A.M. Youth Sheep Show (Prime Show Barn)
11:00-8:00 P.M. Beano at the Beano Hall
12:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
1:00 P.M. Ladies Fry Pan Throwing Contest (Memorial Park)
1:00 P.M. Horse Pulling – 3200 lb. & Under Distance Pull (Vanner Pulling Arena)
2:00 P.M. Youth Baking Contest – Judging (Fudge), (Exhibition Hall)
3:30 P.M. Youth Market Steer Show (Prime Show Barn)
3:30 P.M. Horse Pulling – Three Horse Distance Pull (Vanner Pulling Arena)
5:00 P.M. Youth Market Lamb Show (Prime Show Barn)
6:00 P.M. Horse Pulling – 3200 lb. & Under 12 FT. Pull (Vanner Pulling Arena)
"O. D. Lee Memorial Pull"
Sponsored by Emily’s Restaurant, Windsor, Maine.
7:30 P.M. Lexi James & Wildheart Band - (Grandstand)

August 31, 2025

"Children’s Day"
Gates Open 9:00 A.M.
Gate Admission: 12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time 1:00 P.M.
Giant Midway Opens at 12:00 P.M. – 10:00 P.M.
9:00 A.M. Youth Market Hog Show (Prime Show Barn)
9:15 A.M. Steers & Oxen Show (Lincoln Orff Show Ring)
9:15 A.M. All Day Ancient Ones of Maine Living History (Windsor Historical Society)
10:00 A.M. Youth Beef Show (Prime Show Barn)
10:00 A.M. Church Services (Entertainment Area)
10:00 A.M. Annual Cornhole Tournament (Memorial Park)
11:00-8:00 P.M. Beano at the Beano Hall
11:30 A.M. Kiddie Tractor Pull (Vanner Pulling Arena)
Must enter between 8:00 A.M. & 11:00 A.M. at the Information Booth
Girls: 25-35 lbs. & 36-45 lbs. Boys: 25-35 lbs. & 36-45 lbs.
12:00-8:00 P.M. Purchase ride bracelets $35.00 each, ride until 10:00 P.M.
2:00 P.M. Horse Pulling (Vanner Pulling Arena) 3400 lbs. & Under Distance Pull - Followed by 2 lb Rock – Open any
Weight – Sponsored by Wayne Johnston Trucking & Excavating, Jefferson, ME
& Brandon Johnston Trucking, Jefferson, ME.
6:00 P.M. Animal Costume Class (Prime Show Barn)
6:00 P.M. Horse Pulling – 3400 lb. & Under 12 ft. Pull (Vanner Pulling Arena)
7:30 P.M. Black Cat Hell Driver’s Stunt/Auto Thrill Show (Grandstand)
Admission: Age 12 & up $5.00 (11 & under free)

September 1, 2025

Gates Open 9:00 A.M. Fair closes at 6:00 P.M.
Gate Admission: 12 and up $15.00 (11 and under free)
Harness Horse Racing – Post Time 1:00 P.M.
Giant Midway Opens at 12:00 P.M. – 6:00 P.M
11:00 A.M. Antique Car Show & Parade – MOAL Members Only (Memorial Park)
11:00 A.M. Horse Pulling – Sweepstakes Distance Pull (Vanner Pulling Arena) "Myron Dickey Memorial" Sponsored by;
Dick’s Used Trucks – Chelsea, Me.
12:00-5:00 P.M. Beano at the Beano Hall
12:00-4:00 P.M. Purchase ride bracelets $35.00 each, ride until 6:00 p.m.
12:00 P.M. Youth Market Steer Sale - Followed by Youth Market Lamb Sale - followed by Youth Hog Sale (Prime Show Barn)
1:30 P.M. Horse Pullig – 3300 lbs. & Under Distance Pull – Followed by Special Elimination Sweepstakes 12 Ft. Pull
(Vanner Pulling Arena) - "Myron Dickey Memorial" Sponsored by; Dick’s Used Trucks, Chelsea, Me.

Date: August 23 - September 1, 2025

Location: Windsor Fairgrounds, 82 Ridge Road Windsor, ME 04363

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