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2024 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....

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.

 

Chainsaw Carving Demonstrations

​Stop by and check out the skills!!  All 3 days

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Dog Costume Contest

Dress Up your Pup, see the Contests, Exhibits & Truck Pull tab then Contests for more info  including prizes - Sunday at 3:00 

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Cutest Baby Contest

Bragging rights go to the winner of this contest, see the Contests, Exhibits & Truck Pull tab then Contests for more info including prizes - Sunday 12:30 

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Skillet Throwing Contest

2nd Annual Event see the Contests, Exhibits & Truck Pull tab then Contests for more info including prizes - Saturday 4:30

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Hay Bale Throwing Contest

See the Contests, Exhibits & Truck Pull tab then Contests for more info including prizes - Saturday 5:30

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Makerspace

Back by popular demand and Expanded - 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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Cornhole Tournament - 3rd annual

Cash Prizes - Sunday at 1:00

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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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Aim High Canine Show

High energy, motional show showcasing dog's frisbee, doggie dancing and agility skills that will keep you on the edge of your seat - all 3 days

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Remote Control Racing Tournament

Calling all Remote Control Truck race fans!! You Drive - Race against your friends or family, win and take home a trophy.  No Sign up, just Show up - all 3 days

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Pirate Man Dan Show

Comedy, Magic, Variety and Danger Show - 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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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

5:00 PM   

Gates Open

Grounds

5:00 PM   

Middlesex County Tractor Pullers

Big Pull Ring

6:00 PM

Opening Ceremonies Featuring the Portland High School Band

Grounds

6:15 PM

Remote Control Racing

Grounds

7:00 PM

Aim High Canines

Grounds

7:30 PM

Great Hill Mountain Band

Entertainment Tent

7:45 PM

Remote Control Racing

Grounds

8:15 PM

Pirate Man Dan Comedy & Magic Show

Grounds

8:45 PM

Aim High Canines

Grounds

9:15 PM

Remote Control Racing

Grounds

11:00 PM

Fair Closes

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Saturday

10:30 AM   

Gates Open

Grounds

10:30 AM   

Mass Mini Tractor Pullers

Big Pull Ring

10:30 AM

Dairy Cattle Show

Animal Tent

10:30 AM

Goat Show & Youth Sheep Show

Animal Tent

11:30 AM

Remote Control Racing

Grounds

12:15 PM

Pirate Man Dan Comedy & Magic Show

Grounds

1:00 PM

Ms. Cheryl and her Animal Puppets

Crafts Tent

1:30 PM

Paul Christopher Sienkiewicz 

Entertainment Tent

1:30 PM

Aim High Canines

Grounds

2:00 PM

Draft Horse Drawing Contest 

Small Pull Ring

2:00 PM

Beef Cattle Show

Animal Tent

2:00 PM

Remote Control Racing

Grounds

2:45 PM

Pirate Man Dan Comedy & Magic Show

Grounds

3:00 PM

Tony Rome and the Excuses

Entertainment Tent

3:30 PM

Aim High Canines

Grounds

4:00 PM

Remote Control Racing

Grounds

4:30 PM

Skillet Throwing Contest

Small Pull Ring

5:00 PM

Ms. Cheryl and her Animal Puppets

Crafts Tent

5:00 PM

Small Town Roots

Entertainment Tent

5:30 PM

Hay Bale Toss

Small Pull Ring

5:45 PM

Aim High Canines

Grounds

6:00 PM

Truck Pull

Big Pull Ring

6:30 PM

Remote Control Racing

Grounds

7:15 PM

Pirate Man Dan Comedy & Magic Show

Grounds

8:00 PM

Aim High Canines

Grounds

8:00 PM

Presley & Taylor

Entertainment Tent

10:00 PM

Fair Closes

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Sunday

10:30 AM

Gates Open

Grounds

10:30 AM  

Open and Youth Sheep Show

Animal Tent

10:30 AM  

Carting and Pack Goat & Sheep Show

Animal Tent

11:00 AM

Oxen Drawing Contest 

Small Pull Ring

11:30 AM

Aim High Canines

Grounds

11:30 PM

Makerspace ages 7 & Under

Crafts Tent

12:00 PM

Mud Bog

Big Pull Ring

12:00 PM

Remote Control Racing

Grounds

12:30 PM

Makerspace - ages 8 - 12

Crafts Tent

12:30 PM

Livestock Obstacle Course

Animal Tent

12:30 PM

Baby Contest

Entertainment Tent

12:45 PM

Pirate Man Dan Comedy & Magic Show

Grounds

1:00 PM

Cornhole Tournament

Grounds

1:00 PM

Paul Christopher with Amy Ross

Entertainment Tent

1:30 PM

Police Dog Magnus Meet and Greet

Grounds

2:00 PM

Remote Control Racing

Grounds

2:00 PM

Poultry Showmanship

Animal Tent

2:45 PM

Pirate Man Dan Show

Grounds

3:00 PM

Zep & Co

Entertainment Tent

3:00 PM

Dog Costume Contest

Grounds

3:30 PM

Aim High Canines

Grounds

4:15 PM

Remote Control Racing - FINAL

Grounds

4:45 PM

Aim High Canines

Grounds

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