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
.
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
.
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