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Oct 3, 4 & 5
2025
2025 Entertainment Schedule
Daily Schedule
The Daily Schedule is subject to change
Please check back regularly for the latest updates for this years fair events & entertainment.
Good Stuff you don't want to miss....
Fair Opens at 3:00 on Friday!!
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Irish Step Dance
Mulcahy Academy of Irish Dance. On stage in the Entertainment Tent. What an exciting start to the Fair you don't want to miss this fantastic show. - Friday
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Trashion Show
​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​Trashion Show in the Crafts & Community Tent with prizes sponsored by Savvy Swap and Reboot Eco. All ages encouraged to participate click HERE for more information. - Friday
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Chainsaw Carving Demonstrations
​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​Meet Ben Faraci and see is skills in action. -Saturday and Sunday
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​Powerwheels Derby
1st Ever - Still working on the details. Helmets Required
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​​Makerspace
Explore Technology! Two Sessions: Children under 7 and Children 8 to 12 are invited to join Nate O'Day in the Portland Fair's Makerspace. Build a small functional mobile robot that you can take home (free)! Sunday starting at 11:30. Sign-up in advance beginning September 7th through Facebook.
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Police Dog Meet and Greet
Magnus, Portland's own police dog, his skills will amaze you - Sunday at 1:30
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Storytime with Ms. Cheryl and her Puppets
Come listen to animal puppets tell their stories. This is a super fun adventure for children under 10. Saturday
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Nature Nick's Animal Adventure
Come meet owls, falcons, snakes, alligators, foxes, armadillos, turtles, and even a Chilean flamingo on this wildlife adventure - all 3 days
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Arestov's Aerobatic Extravaganza
Fast-paced, family-friendly, exciting display of thrills and skills that will put audiences on the edge of their seats - all 3 days
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Carnival
Featuring Rides and Games - all 3 days (not included in the price of admission)
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Petting Zoo & Pony Rides
Feed the animals, watch them play and then take a pony ride! The zoo and the pony rides will be available all weekend long. Pony rides are not included in the cost of admission. all 3 days
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Entertainment Tent
The Portland Fair has partnered with Eli Cannons Tap Room and Concentric Brewing. They will be pouring an excellent selection of draft beer in addition to wines and hard seltzers.
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Schedule
Friday
3:00 PM
Gates Open
Gates Open
4:00 PM
Band - TBD
Entertainment Tent
5:00 PM
Middlesex County Tractor Pullers
Big Pull Ring
5:00 PM
Nature Nick's Animal Adventure
Grounds
5:30 PM
Opening Ceremonies Featuring the Portland High School Band
Grounds
6:00 PM
Irish Step Dance
Entertainment Tent
6:00 PM
Arestov's Acrobatic Extravaganza
Grounds
6:30 PM
Trashion Show
Crafts & Community Tent
7:00 PM
Nature Nick's Animal Adventure
Grounds
7:15 PM
Small Town Roots
Entertainment Tent
8:00 PM
Arestov's Acrobatic Extravaganza
Grounds
9:00 PM
Nature Nick's Animal Adventure
Grounds
Saturday
10:30 AM
Gates Open
Grounds
10:30 AM
Mass Mini Tractor Pullers
Big Pull Ring
10:45 AM
Dairy Cattle Show
Animal Tent
10:45 AM
Goat Show & Youth Sheep Show
Animal Tent
11:00 AM
XXXX w Cat Owens
Crafts & Community Tent
12:00 PM
Paul Christopher with Mary Ross
Entertainment Tent
1:00 PM
Nature Nick's Animal Adventure
Grounds
1:30 PM
Ms. Cheryl and her Animal Puppets
Crafts & Community Tent
2:00 PM
Draft Horse Drawing Contest
Small Pull Ring
2:00 PM
Arestov's Acrobatic Extravaganza
Animal Tent
3:00 PM
Powerwheels Derby
TBD
3:00 PM
Centerline
Entertainment Tent
4:00 PM
Nature Nick's Animal Adventure
Grounds
5:00 PM
Arestov's Acrobatic Extravaganza
Grounds
4:30 PM
Skillet Throwing Contest
Small Pull Ring
5:00 PM
Ms. Cheryl and her Animal Puppets
Crafts Tent
5:00 PM
Truck Pull
Big Pull Ring
5:30 PM
Hay Bale Toss
TBD
7:00 PM
Jeff Pitchell
Entertainment Tent
7:00 PM
Nature Nick's Animal Adventure
Grounds
8:00 PM
Arestov's Acrobatic Extravaganza
Grounds
10:00 PM
Fair Closes
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Sunday
10:30 AM
Gates Open
Grounds
10:30 AM
Antique Tractor Pull
Big Pull Ring
10:45 AM
Open and Youth Sheep Show
Animal Tent
10:45 AM
Carting and Pack Goat & Sheep Show
Animal Tent
11:00 AM
Mud Bog
Bog Pit
11:00 AM
Oxen Drawing Contest
Small Pull Ring
11:30 AM
Nature Nick's Animal Adventure
Grounds
11:30 PM
Makerspace ages 7 & Under
Crafts & Community Tent
12:30 PM
Arestov's Acrobatic Extravaganza
Grounds
12:30 PM
Makerspace - ages 8 - 12
Crafts Tent
12:30 PM
Livestock Obstacle Course
Animal Tent
1:00 PM
Paul Christopher with Amy Ross
Entertainment Tent
1:00 PM
Police Dog Magnus Meet and Greet
Grounds
1:30 PM
Nature Nick's Animal Adventure
Grounds
2:00 PM
Poultry Showmanship
Animal Tent
2:30 PM
Arestov's Acrobatic Extravaganza
Grounds
3:00 PM
Cobblestone Roots
Entertainment Tent
3:30 PM
Nature Nick's Animal Adventure
Grounds
4:30 PM
Arestov's Acrobatic Extravaganza
Grounds
6:00 PM
Fair Closes
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