2022 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....
Dog Costume Contest
Dress Up your Pup, see the Exhibits & Truck Pull tab then Contests for more info including prizes - Sunday at 2:00
Karaoke hosted by Rob Valli
Do you have what it takes to get up on the big stage in the Entertainment Tent (I know I don't, I can't even whistle) - Saturday at 4:00
Trick or Treat for Kids
Kids 12 and under at participating vendors, you provide the costume we will provide the bag - Saturday 4 - 7
Cornhole Tournament
Cash Prizes - Sunday at 1:00
Bwana Jim's Wildlife Show
Crazy and Wild Show featuring Exotic Animals - all 3 days
Pirate Man Dan Show
Comedy, Magic, Variety and Danger Show - all 3 days
Sunday Sports
3 Big Screen TVs with Football, Post Season Baseball and NASCAR - Sunday 1:00
Coleman's Midway
Featuring Rides and Games - all 3 days (not included in the price of admission)
Hat City Axes
Axe throwing - all 3 days (not included with the price of admission)
Wine Tasting and Seminar
Think you know wine? Think again... - Sat & Sun
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)
PHS Class of 1967
The Portland Fair welcomes the class of 1967
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
Antique Tractor Pull
Big Pull Ring
5:00 PM
Small Town Roots
Entertainment Tent
5:45 PM
Opening Cermonies
Entertainment Tent
6:15 PM
Bwana Jim Wildlife Show
Grounds
7:15 PM
Pirate Man Dan Comedy, Magic Show
Grounds
8:00 PM
Hazzard County
Entertainment Tent
8:15 PM
Bwana Jim Wildlife Show
Grounds
Saturday
10:30 AM
Helicopter Rides
All Day
10:30 AM
Middlesex Country Garden Tractor Pullers
Big Pull Ring
10:30 AM
Dairy Cattle Show
Cattle Barn
10:30 AM
Goat Show & Youth Sheep Show
Livestock Tent
12:00 PM
Trivia - Disney
Entertainment Tent
12:00 PM
Bwana Jim's Wildlife Show
Grounds
12:45 PM
Wine Tasting & Seminar
Entertainment Tent
1:00 PM
Pirate Man Dan Show
Grounds
1:30 PM
That 70's Project
Entertainment Tent
2:00 PM
Draft Horse Drawing Contest
Small Pull Ring
2:00 PM
Beef Cattle Show
Cattle Barn
2:30 PM
Bwana Jim's Wildlife Show
Grounds
3:30 PM
Pirate Man Dan Show
Grounds
4:00 PM
Trick or Treat for Kids
Grounds
4:00 PM
Karaoke hosted by Rob Valli
Entertainment Tent
4:00 PM
Truck Pull
Big Pull Ring
5:00 PM
Bwana Jim's Wildlife Show
Grounds
6:00 PM
Pirate Man Dan Show
Grounds
6:00 PM
Wine Tasting and Seminar
Entertainment Tent
7:00 PM
Jimmy Kenny and the Pirate Beach Band
Entertainment Tent
7:30 PM
Bwana Jim's Wildlife Show
Grounds
Sunday
10:30 AM
Dog Star Rescue
Grounds
10:30 AM
Helicopter Rides
All Day
10:30 AM
Open and Youth Sheep Show
Livestock Tent
10:30 AM
Carting and Pack Goat & Sheep Show
Livestock Tent
11:00 AM
Bwana Jim's Wildlife Show
Grounds
11:00 AM
Square Dancing
Entertainment Tent
11:00 AM
Oxen Drawing Contest
Small Pull Ring
12:00 AM
Sargent Jim Kelley K9 Demonstration
Grounds
12:30 PM
Pirate Man Dan Show
Grounds
12:30 PM
Livestock Obstacle Course
Cattle Barn
1:00 PM
Truck Pull
Big Pull Ring
1:00 PM
The Savvy Swap Fashion Show
Entertainment Tent
1:00 PM
Rabbit Showmanship & Spinning Exhibit
Livestock Tent
1:00 PM
Sports Ticket - NFL Football & Nascar
Entertainment Tent
1:00 PM
Cornhole Tournament
Entertainment Tent
1:30 PM
Bwana Jim's Wildlife Show
Grounds
2:00 PM
Wine Tasting and Seminar
Entertainment Tent
2:00 PM
Dog Costume Contest
Grounds
2:00 PM
Poultry Showmanship
Livestock Tent
2:30 PM
Pirate Man Dan Show
Grounds
3:00 PM
Wine Tasting and Seminar
Entertainment Tent
3:30 PM
Bwana Jim's Wildlife Show
Grounds
4:30 PM
Pirate Man Dan Show
Grounds
4:30 PM
Wine Tasting and Seminar
Entertainment Tent