Community Calendar

Maine's 2nd Largest Agricultural Fair, featuring Harness Racing, Giant Rockwell Amusements Midway, Extensive Exhibition Hall, Livestock, Agricultural Education, Historical Museum, Truck/Tractor/Livestock Pulling Events, Live Music, 2 nights of Demolition Derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and So Much More!
General Admission: Children 11 & Under Free / Ages 12 & up $15
Hours: 9am-10pm 8/23-8/31, 9am-6pm on 9/1.
Season Passes $100 AT GATES 1 & 4, covers admission for all 10 days.
Senior Days (60+) $5 on Mon 8/25 & Thurs 8/28.
Veteran's Day Thurs 8/28 free with valid Military ID.
***No Pets Allowed fully trained service animals only***No Glass, Alcohol or Weapons***
Our Parking is always FREE
Rockwell Midway Rides Open at Noon on Weekends and Labor Day, and 3pm on Weekdays. $35 Ride bracelets available every day. Discount pre-buy links will be on our website.
Harness Racing Post Times Weekends 1pm, Weekdays 3pm. *No harness racing on Weds.
See our full program at www.windsorfair.com for schedule of events, entertainment lineup & premium book for all entry information. https://www.facebook.com/WindsorFair
We look forward to seeing you!
Email Questions to: windsorfairinfo@gmail.com

Maine's 2nd largest agricultural fair, featuring a large Exhibition Hall, giant Rockwell Amusements midway, Livestock, Truck and Tractor pulls, Livestock barns and events, Harness Racing everyday but Weds., live music, giant pumpkin contest, two nights of demolition derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and so much more! We open at 9am each day, closing at 10pm each night, except 6pm on Labor Day. There is no alcohol, glass or weapons allowed on the grounds. No pets allowed, fully trained service animals only.

The Crooked River Gathering takes place August 28th–31st, 2025. Located in Hiram, Maine—just 45 minutes from Portland. Hosted on a historic riverside fairground, this unique four-day event is a celebration of community, creativity, and connection through bluegrass and old-time music, homesteading, artisan craft, and folk culture. The weekend features live performances, jam circles, hands-on workshops, craft vendors, food trucks, skillshares, and community meetups. The event is free for kids and free on-site camping is available for all attendees, making it an immersive and family-friendly experience for music lovers, makers, and nature enthusiasts alike. Full details at www.crookedriverarts.org.

Maine's 2nd Largest Agricultural Fair, featuring Harness Racing, Giant Rockwell Amusements Midway, Extensive Exhibition Hall, Livestock, Agricultural Education, Historical Museum, Truck/Tractor/Livestock Pulling Events, Live Music, 2 nights of Demolition Derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and So Much More!
General Admission: Children 11 & Under Free / Ages 12 & up $15
Hours: 9am-10pm 8/23-8/31, 9am-6pm on 9/1.
Season Passes $100 AT GATES 1 & 4, covers admission for all 10 days.
Senior Days (60+) $5 on Mon 8/25 & Thurs 8/28.
Veteran's Day Thurs 8/28 free with valid Military ID.
***No Pets Allowed fully trained service animals only***No Glass, Alcohol or Weapons***
Our Parking is always FREE
Rockwell Midway Rides Open at Noon on Weekends and Labor Day, and 3pm on Weekdays. $35 Ride bracelets available every day. Discount pre-buy links will be on our website.
Harness Racing Post Times Weekends 1pm, Weekdays 3pm. *No harness racing on Weds.
See our full program at www.windsorfair.com for schedule of events, entertainment lineup & premium book for all entry information. https://www.facebook.com/WindsorFair
We look forward to seeing you!
Email Questions to: windsorfairinfo@gmail.com

Maine's 2nd largest agricultural fair, featuring a large Exhibition Hall, giant Rockwell Amusements midway, Livestock, Truck and Tractor pulls, Livestock barns and events, Harness Racing everyday but Weds., live music, giant pumpkin contest, two nights of demolition derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and so much more! We open at 9am each day, closing at 10pm each night, except 6pm on Labor Day. There is no alcohol, glass or weapons allowed on the grounds. No pets allowed, fully trained service animals only.

The Crooked River Gathering takes place August 28th–31st, 2025. Located in Hiram, Maine—just 45 minutes from Portland. Hosted on a historic riverside fairground, this unique four-day event is a celebration of community, creativity, and connection through bluegrass and old-time music, homesteading, artisan craft, and folk culture. The weekend features live performances, jam circles, hands-on workshops, craft vendors, food trucks, skillshares, and community meetups. The event is free for kids and free on-site camping is available for all attendees, making it an immersive and family-friendly experience for music lovers, makers, and nature enthusiasts alike. Full details at www.crookedriverarts.org.

Maine's 2nd Largest Agricultural Fair, featuring Harness Racing, Giant Rockwell Amusements Midway, Extensive Exhibition Hall, Livestock, Agricultural Education, Historical Museum, Truck/Tractor/Livestock Pulling Events, Live Music, 2 nights of Demolition Derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and So Much More!
General Admission: Children 11 & Under Free / Ages 12 & up $15
Hours: 9am-10pm 8/23-8/31, 9am-6pm on 9/1.
Season Passes $100 AT GATES 1 & 4, covers admission for all 10 days.
Senior Days (60+) $5 on Mon 8/25 & Thurs 8/28.
Veteran's Day Thurs 8/28 free with valid Military ID.
***No Pets Allowed fully trained service animals only***No Glass, Alcohol or Weapons***
Our Parking is always FREE
Rockwell Midway Rides Open at Noon on Weekends and Labor Day, and 3pm on Weekdays. $35 Ride bracelets available every day. Discount pre-buy links will be on our website.
Harness Racing Post Times Weekends 1pm, Weekdays 3pm. *No harness racing on Weds.
See our full program at www.windsorfair.com for schedule of events, entertainment lineup & premium book for all entry information. https://www.facebook.com/WindsorFair
We look forward to seeing you!
Email Questions to: windsorfairinfo@gmail.com

Maine's 2nd largest agricultural fair, featuring a large Exhibition Hall, giant Rockwell Amusements midway, Livestock, Truck and Tractor pulls, Livestock barns and events, Harness Racing everyday but Weds., live music, giant pumpkin contest, two nights of demolition derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and so much more! We open at 9am each day, closing at 10pm each night, except 6pm on Labor Day. There is no alcohol, glass or weapons allowed on the grounds. No pets allowed, fully trained service animals only.

The Crooked River Gathering takes place August 28th–31st, 2025. Located in Hiram, Maine—just 45 minutes from Portland. Hosted on a historic riverside fairground, this unique four-day event is a celebration of community, creativity, and connection through bluegrass and old-time music, homesteading, artisan craft, and folk culture. The weekend features live performances, jam circles, hands-on workshops, craft vendors, food trucks, skillshares, and community meetups. The event is free for kids and free on-site camping is available for all attendees, making it an immersive and family-friendly experience for music lovers, makers, and nature enthusiasts alike. Full details at www.crookedriverarts.org.

Maine's 2nd Largest Agricultural Fair, featuring Harness Racing, Giant Rockwell Amusements Midway, Extensive Exhibition Hall, Livestock, Agricultural Education, Historical Museum, Truck/Tractor/Livestock Pulling Events, Live Music, 2 nights of Demolition Derbies, Woodsman's Day, Black Cat Hell Drivers Auto Stunt Thrill Show and So Much More!
General Admission: Children 11 & Under Free / Ages 12 & up $15
Hours: 9am-10pm 8/23-8/31, 9am-6pm on 9/1.
Season Passes $100 AT GATES 1 & 4, covers admission for all 10 days.
Senior Days (60+) $5 on Mon 8/25 & Thurs 8/28.
Veteran's Day Thurs 8/28 free with valid Military ID.
***No Pets Allowed fully trained service animals only***No Glass, Alcohol or Weapons***
Our Parking is always FREE
Rockwell Midway Rides Open at Noon on Weekends and Labor Day, and 3pm on Weekdays. $35 Ride bracelets available every day. Discount pre-buy links will be on our website.
Harness Racing Post Times Weekends 1pm, Weekdays 3pm. *No harness racing on Weds.
See our full program at www.windsorfair.com for schedule of events, entertainment lineup & premium book for all entry information. https://www.facebook.com/WindsorFair
We look forward to seeing you!
Email Questions to: windsorfairinfo@gmail.com