Home Uncategorized Windsor Fair in Maine – What to Expect

Windsor Fair in Maine – What to Expect

by Derrick Grant
Windsor Fair rides
The Windsor Fair is an annual Central Maine agricultural fair in the town of Windsor.

The Windsor Fair is an annual event with a variety of midway rides, games, food booths, agricultural displays, and events. It runs for nine days typically at the very end of August and into the first week of September. It is an event attended mainly by Maine residents residing in the area. Unlike the much larger Fryeburg Fair, few tourists make their way to the Windsor Fair.

The fair has been going on since 1888. It’s been around a while! Given its longevity, the fair also holds a museum complex that consists of 12 buildings and has displays from the 19th and early 20th centuries. There are different historical demonstrations held over the week such as a hand-operated printing press and a blacksmith shop.

Official information on the Windsor Fair can be found on their website and on their Facebook page.

If you are thinking about attending, make sure to read my Helpful Hints section toward the end of this article.

“Rural” and “blue collar” are perhaps two ways to describe this fair, but that is a common way to describe most agricultural fairs. As such, it is a place to find a whole lot of flannel shirts, Carharts, camo Crocs, and Chippewa boots.

There is camping available for those that want to spend the entire week there and a season pass for admission can be purchased.

Adults like the fair for the main events, agricultural displays, and fair food. Kids enjoy it for the rides and because it occurs right before they go back to school, and it’s the summer’s last way to see and be seen before school starts.

Main Events

There is a main event held on each evening. The night I attended (a Sunday) there was demolition derby. Local residents fix up their old junker cars (yes, they must be “fixed” to adhere to safety rules) and smash each other until there’s one car left running.

packed grandstands
People gathering to watch the demolition derby.

This year’s fair had two instances of the demolition derby on different nights, a testament to the popularity of the event. Other main events included the truck & tractor pull, fireworks, live music, and the Black Cat Hell Drivers (additional fee).

demolition derby
Smoke billows out from cars in the demolition derby.

Harness racing is another (almost daily) event that attracts many visitors to the fairgrounds during the day. Place your bets!

Woodsmen’s Day is another popular event held during a weekday that includes events, demonstrations, and competitions covering wood chopping, log rolling, buck sawing, crosscut sawing, and axe throwing.

Fair Food

Fair food is an attraction of any fair. Fairgoers can find the standard fair… fare: hand cut fries, fried fish and chips, sausage subs, dough boys, kettle corn, candy apples, cotton candy, smoothies, shaved ice, deep fried everything, and of course, burgers, hot dogs, and fries.

Italian sausage food booth
Fairgoers sit down for an Italian sausage.

These foods aren’t the healthiest options, but tucked away in a corner I was also able to find Chinese food options.


The midway is typical of most small fairs. You have various rides for kids of different ages and the standard balloon popping, water gun squirting fairs that can yield plastic prizes and stuffed animals for anyone skilled enough to win.

zipper fair ride
The Zipper, one of a few dozen rides at the fair.

Rides at the Windsor Fair included the Zipper, Tilt-a-Whirl, Tornado, Starship 3000, different slides, a merry go round, flying swings, etc.

fair games
Fair goers have enough game options to try to win a prize for a child or a date.


The Windsor Fair has its roots in agriculture, as most Maine fairs do. While the main attractions of the fair may have changed with the times as Maine became less agriculture centric, livestock and farming are still a central component of the fair.

Fair goers will find an assortment of goats, chickens, cattle, horses, pigs, and more. Competitions are held and judged by volunteers.

cattle in barn
Tony, the Maine Texas Longhorn attracting attention at the Windsor Fair.

The same displays and competitions are held for fruits and vegetables, recipes, etc.

largest pumpkin competition
One could make a lot of pumpkin spice with these big boys.

There was also a small “farmers market” of sorts where a farmer had a booth selling locally-grown produce. Other booths sold homemade soap, Maine maple syrup, etc. Farm equipment was also on display.

Windsor Fair Helpful Hints

If you’re planning to attend the fair, these helpful hints might make the experience a bit better:

  • Don’t just randomly attend any day. Check the fair program for the main event and pricing. Some days there are ride bracelets available which can save money if you have kids that want to go on rides non-stop. Other days pricing may be half price.
  • As you approach the fair from the south entrance, there is a private parking area where the landowner will charge $5.00 to park. This will get you slightly closer than the main parking area associated with the fair, but for a few more steps you can park on fairground property for free.
  • The fair will be busiest on the weekends, but crowd size is still manageable. If you want quiet, attend during the day on a weekday.

Have YOU attended the Windsor Fair? What were your thoughts? Let us know in the comments section.

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