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2023 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....

High Point Archery Shoot 

Back by popular demand - Middlesex 4-H Shooting Sports Program presents a High Point Archery Shoot run by the USA Archery Association. Beginners and Experts, all are welcome! (not included with the price of admission)

 

Dog Costume Contest

Dress Up your Pup, see the Contests, Exhibits & Truck Pull tab then Contests for more info  including prizes - Sunday at 2:00 

 

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 - Saturday 4:00 

Skillet Throwing Contest

Don't miss the 1st ever at the Fair! see the Contests, Exhibits & Truck Pull tab then Contests for more info including prizes - Saturday 4:30

Makerspace

Explore Technology! Children 11 and under 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 12:30

Labs 4 Rescue

Furry face is waiting for adoption.  Come be a hero! Sunday at 1:00

Police Dog Demonstration

Magnus, Portland's own police dog, his skills will amaze you - Sunday at 1:00

Cornhole Tournament

Cash Prizes - Sunday at 2:00

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

Nature Nick's Animal Adventure

Exotic Animal Show - all 3 days

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

Pirate Man Dan Show

Comedy, Magic, Variety and Danger Show - all 3 days

Coleman's Midway

Featuring Rides and Games - all 3 days (not included in the price of admission)

Records & Burpee Children's Zoo

Petting Zoo & all sorts of different feathered and furred friends to make - all 3 days

Sickline Carving

Chainsaw carving demonstrations - all 3 days

Helicopter Rides

Saturday and Sunday  (not included with the price of admission)

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.

Schedule

Friday

5:00 PM   

Gates Open

Grounds

5:00 PM   

Middlesex Garden Tractor Pullers

Big Pull Ring

5:30 PM

Opening Ceremonies Featuring the Portland High School Band

Grounds

6:15 PM

Remote Control Racing

Grounds

7:00 PM

Nature Nick's Animal Adventure Show

Grounds

7:00 PM

Small Town Roots

Entertainment Tent

7:45 PM

Remote Control Racing

Grounds

8:15 PM

Pirate Man Dan Comedy & Magic Show

Grounds

8:45 PM

Nature Nick's Animal Adventure Show

Grounds

11:00 PM

Fair Closes

.

Saturday

10:30 AM   

Gates Open

Grounds

10:30 AM   

Helicopter Rides

All Day

10:30 AM   

Antique Tractor Pull

Big Pull Ring

10:30 AM

Dairy Cattle Show

Cattle Barn

10:30 AM

Goat Show & Youth Sheep Show

Livestock Barn

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

Livestock Barn

1:30 PM

Backstage Pass

Entertainment Tent

1:30 PM

Nature Nick's Animal Adventure Show

Grounds

2:00 PM

Draft Horse Drawing Contest

Small Pull Ring

2:00 PM

Beef Cattle Show

Cattle Barn

2:00 PM

Remote Control Racing

Grounds

2:45 PM

Pirate Man Dan Comedy & Magic Show

Grounds

3:30 PM

Nature Nick's Animal Adventure Show

Grounds

4:00 PM

Remote Control Racing

Grounds

4:00 PM

Baby Contest

Grounds

4:30 PM

Skillet Throwing Contest

Grounds

5:00 PM

Ms. Cheryl and her Animal Puppets

Livestock Tent

5:00 PM

Great Hill Mountain Band

Entertainment Tent

5:45 PM

Nature Nick's Animal Adventure Show

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

Nature Nick's Animal Adventure Show

Grounds

8:00 PM

Presley & Taylor

Entertainment Tent

10:00 PM

Fair Closes

.

Sunday

10:30 AM

Gates Open

Grounds

10:30 AM

Helicopter Rides

All Day

10:30 AM  

Open and Youth Sheep Show

Livestock Barn

10:30 AM  

Carting and Pack Goat & Sheep Show

Livestock Barn

11:00 AM

Oxen Drawing Contest

Small Pull Ring

11:30 AM

Nature Nick's Animal Adventure

Grounds

12:00 PM

Karen & Norm Duo

Entertainment Tent

12:00 PM

Remote Control Racing

Grounds

12:30 PM

Makerspace - Robot Building

Grounds

12:30 PM

Livestock Obstacle Course

Cattle Barn

12:45 PM

Pirate Man Dan Comedy & Magic Show

Grounds

1:00 PM

Labs 4 Rescue

Grounds

1:00 PM

Mud Bog

Big Pull Ring

2:00 PM

Robert J.

Entertainment Tent

2:00 PM

Dog Costume Contest

Grounds

1:15 PM

Sargent Jim Kelley K9 Demonstration

Grounds

2:00 PM

Remote Control Racing

Grounds

2:00 PM

Poultry Showmanship

Livestock Barn

2:45 PM

Pirate Man Dan Show

Grounds

3:00 PM

Cornhole Tournament

Grounds

3:30 PM

Nature Nick's Animal Adventure

Grounds

3:30 PM

Paul Christopher Sienkiewicz

Entertainment Tent

4:15 PM

Remote Control Racing - FINAL

Grounds

4:45 PM

Nature Nick's Animal Adventure

Grounds

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