Daily Schedule

The Daily Schedule is subject to change
Please check back regularly for the latest updates for this years fair events & entertainment.
 

During the Fair
You can get quick access to this schedule on your mobile device at any of the QR stations around the fair.
- OR -
Navigate to "Portlandfair.com/Entertainment"

Daily Events - Great Entertainment Every Day

  • Chainsaw Carving Demos

  • Helicopter Rides

  • Circle K Petting Zoo 

  • Coleman Bros Midway ~ wristbands on Fri. & Sun. ~ MORE RIDES!!!

  • Rosaire's Royal Racers ~ Racing Pigs

  • Pirate Man Dan and his Bubble Ship

  • High Point Archery Shoot

  • Wine Tasting & Seminar ~ win a bottle of wine!

Friday October 4th

Antique Tractor Pull

5:00 PM | Mechanical Pull Ring

Opening Ceremonies - Featuring the PHS Band

6:00 PM | On Grounds

Draft Pony Drawing Contest

6:00 PM | Animal Pull Ring

Wine Tasting & Seminar

6:30 PM | Entertainment Tent

Rasaire's Royal Racers

6:45 PM | 8:45 PM | On Grounds

Jamie's Junk Show

7:30 PM | Entertainment Tent - On Stage

Saturday October 5th

Dairy Cattle Show

10:00 AM | Cattle Barn

Middlesex County Tractor Pullers 

10:00 AM | Mechanical Pull Ring

Goat and Youth Sheep Shows

10:00 AM | Livestock Tent

Miniature Draft Horse Drawing Contest

10:00 AM | Animal Pull Ring

Adelaide Punkin

12:00 PM | Entertainment Tent - On Stage

Rosaire's Royal Racers

12:00 PM | 2:30 PM | 5:00 PM | 7:30 PM | On Grounds

Beef Cattle Show

2:00 PM | Cattle Barn

Draft Horse Drawing Contest

2:00 PM | Animal Pull Ring

Wine Tasting & Seminar

2:00 PM | 5:00 PM | Entertainment Tent

70's Project

3:00 PM | Entertainment Tent - On Stage

Truck Pull - hosted by CT Truck Pullers

4:00 PM | Mechanical Pull Ring

Jeff Pitchell with special guest Michael Allman

7:00 PM | Entertainment Tent - On Stage

Sunday October 6th

Open & Youth Sheep Show
10:00 AM I Livestock Tent
Carting & Pack Goat/Sheep Show
10:00 AM I Livestock Tent
Trivia ~ Win Prizes
10:30 AM I Entertainment Tent
Draft Oxen/Cattle Drawing Contest
11:00 AM I Animal Pull Ring
Rosaire's Royal Racers
11:30 AM I 2:00 PM I 4:30 PM I On Grounds
Bend in the River
11:30 PM I Entertainment Tent - On Stage
Connecticut Greyhound Adoption
11:00 AM I On Grounds
Wine Tasting & Seminar
12:15 PM I Entertainment Tent
Livestock Obstacle Course
12:00 PM I Cattle Barn
Dirty Ditch Mud Runs
12:00 PM I Mechanical Pull Ring
Spinning Exhibition
1:00 PM I Livestock Tent
Rabbit Showmanship
1:00 PM I Livestock Tent
Poultry Showmanship
2:00 PM I Livestock Tent
Gunsmoke
3:00 PM I Entertainment Tent - On Stage
Spinning Contest
3:00 PM I Livestock Tent
Livestock Costume Parade
3:00 PM I On Grounds