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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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