Entertainment
Click each date below to see what entertainment is happening on each day! If you're looking for a list of everything that is being held in our Contest Arena, check out that list below.
Don't forget to click on our Daily Entertainment section also, that's where you will find showtimes for our entertainment that repeats throughout the week and isn't included on the day specific lists!
Dean Crawford & The Dunn's River Band: 7:00 pm & 8:30 pm at the Entertainment Stage.
Dean has produced five CD's and has sold over 24,000 copies and has made numerous TV appearances in the market. His songs are a main staple on several large market and internet radio stations throughout the region. Dean leads a mighty six piece band that would be the envy of any national touring country act on the scene today. The band covers both contemporary and traditional country music which enables them to please any audience anywhere! A faithful and growing fan base is what keeps this group on the rise with sold out appearances and souvenir sales that eclipse any other group in the region.
Dean and Dunn's have opened up for notable Nashville greats such as Neal McCoy, Buddy Jewel, Montgomery Gentry, Jamie O'Neil, and Bucky Covington. They were called upon and honored to accept the invitation to open for the greatest country singer of all time, in his last public appearance.....the Possum, Mr. George Jones!!
Square Dance Demonstration: 4:00 pm at the Entertainment Stage.
Square Dance: 7:00 pm at the 4-H Activities Hall.
All sponsored by the Tom Thumb Dance Club.
Michael Christopher: 7:00 pm and 8:30 pm on the Entertainment Stage.
Michael Christopher found perseverance and grit during his childhood growing up in rural Pennsylvania, and the lessons he learned along the way would be right at home in the lyrics of today’s most popular country music.
For the last decade, Michael’s focus and passion has been on music: writing, singing, and performing in clubs, amphitheaters, and festivals across the country. While headlining events across the northeast and beyond, Michael has also opened for some major country stars, including Tyler Farr, Sammy Kershaw, Lonestar, Chris Lane, Jamey Johnson, Phil Vassar, William Michael Morgan and Walker Hayes. His guitar-heavy, rock-edged sound intertwines with invocative lyrical virtuosity and positions him with elite company in the country music scene.
In his self-titled album, Michael worked with an exclusive group of hit songwriters and producers including Dennis D’Amico recording at Ronnie’s Place/Black River Entertainment Studios, and Grammy-Award winning engineer Jamie Tate at The Rukkus Room. The result is a twelve-song anecdote of life and love that not only displays Michael’s flexibility and ingenuity as a songwriter, but also expands the boundaries of the country music genre. “There is something for everyone on this record. We really tried to offer a perspective, a sound and a voice that is relatable for everyone…no matter what you’re feeling, no matter what you’ve been through…this record has something for you,” mentions Michael.
To follow up his debut album, Michael decided to do an EP devoted to his favorite season; summer. “Summer Vibes” is an eclectic modern country summer time soundtrack!
With a ton of new music under his belt and a full tour schedule, Michael Christopher continues to excel on his way to the next chapter of his career.
Outlaws & Peacemakers (Wild West Reenactment): 4:00 pm, 6:00 pm, and 8:00 pm in the Contest Arena.
This local Wild West reenactment group will be demonstrating the art of reenactment, how they stay safe, and the dangers of using blank ammunition.
Daisy Road: 7:00 pm and 8:30 pm on the Entertainment Stage.
Sheep Dog Herding Demonstration: 5:00 pm & 7:00 pm at the Horse Ring.
Since 2017, attendees have enjoyed sheepdog herding demonstrations at the fair. Once again, Nancy Cox Starkey of Mt. Airy, MD, will provide the commentary, and A J Hesketh-Tutton of West Friendship, MD, will put the sheepdogs through their paces herding a flock of sheep. Nothing short of impressive are the skills, talent, and ability of the handlers and their dogs. Watch and learn as they work in partnership to maneuver the sheep around the ring and through various obstacles. Always a crowd favorite!
Senior Day Activities: 10:00 am - 3:00 pm in the 4-H Activities Hall.
- Maryland Accordion Club Concert: 10:00 am - 11:30 am
- Bingo: 11:30 am - 12:30 pm
- Will Williams: 12:30 pm - 1:15 pm
- Bingo: 1:15 pm - 2:15 pm
- Will Williams: 2:15 pm - 3:00 pm
Farm-to-Fork Face-Off 2026: Howard County's Best Steak Showdown! 6:00 pm - 8:00 pm at the 4-H Activities Hall/Patio.
Chefs selected by the Howard County Office of Agriculture will compete at the Fair in an epic steak showdown for the title of Howard County’s Best Steak. In this sizzling competition, the chefs will use locally raised beef, and fresh-picked produce, along with their choice of special ingredients to showcase their own recipes and signature styles.
The Farm-to-Fork Face-Off is all about lifting up Howard County’s farm and food communities by spotlighting fresh, seasonal ingredients and the chefs who transform them. This event connects farmers, chefs, and residents in a fun, flavor-packed evening that promotes sustainable, local food and shines a light on the incredible talent in our region.
Jay Henley & the Stonebroke Band: 7:00 pm and 8:30 pm on the Entertainment Stage.
Jay D. Henley likes playing in his old stomping grounds. The summer carnival season gives him plenty of opportunities to play for the hometown crowd.
Henley grew up on a Mount Airy farm where he spent a lot of time milking cows and developed a work ethic that continues to serve him well.
Streamline Rocks: 7:00 pm & 8:30 pm on the Entertainment Stage.
Sheep Dog Herding Demonstration: 5:00 pm & 7:00 pm in the Horse Ring.
Since 2017, attendees have enjoyed sheepdog herding demonstrations at the fair. Once again, Nancy Cox Starkey of Mt. Airy, MD, will provide the commentary, and A J Hesketh-Tutton of West Friendship, MD, will put the sheepdogs through their paces herding a flock of sheep. Nothing short of impressive are the skills, talent, and ability of the handlers and their dogs. Watch and learn as they work in partnership to maneuver the sheep around the ring and through various obstacles. Always a crowd favorite!
Browningsville Cornet Band: 7:00 pm on the 4-H Activities Hall Patio.
Talent & Variety Show: 7:00 pm at the Entertainment Stage.
My Lady's Manor Driving Club, founded in 1979, is a group of local, carriage driving enthusiasts. Their purpose is to promote the owning, training, driving, and exhibiting of all breeds of equines; and to hold activities that will best contribute to those objectives. Members of the club are encouraged to participate with all types of horses, ponies, donkeys, and vehicles.
Stone Ridge Boys: 7:00 pm & 8:30 pm on the Entertainment Stage.
Returning to the Howard County Fair this year, The Stone Ridge boys are certainly no strangers to the area. This talented, Maryland based County Music duo is comprised of James Naill and Brandon Reeves. They stay busy performing at local establishments, festivals, and private parties where their musical offerings are enjoyed by all.
Red, White, & Blue Parade of Horse Breeds: 4:00 pm at the Horse Show Ring.
Watch as a variety of horse breeds take the spotlight in the Parade of Horse Breeds! An announcer will highlight the unique characteristics and talents of each breed. After the event, there will be an opportunity for you to talk to the exhibitors and to get up close with these incredible animal
Cody Clayton Eagle: 7:00 pm & 8:30 pm on the Entertainment Stage.
Cody Clayton Eagle is an accomplished country singer/songwriter hailing from the hills of West Virginia. Cody’s musical ability is only matched by his humble demeanor and dedication to his craft which are two traits that are very difficult to maintain. While Cody’s career in music is still fresh, his accomplishments match that of a veteran in the industry. Cody has shared the stage with a number of talented individuals. But of all of his accomplishments, his most well-known came in the form of a gold ticket to Hollywood given to him by the judges of ABC’s American Idol in 2019.
Many artists would use validation of three yes votes in one of the country’s biggest talent shows to slack off and take a back seat, but not Cody. This opportunity lit a fire in Cody to dedicate much of his time to perfecting his craft and begin his journey as a professional singer/songwriter. Shortly after his trip to Hollywood, Cody began working with a group of highly talented musicians and producers to help produce his first single “I Will Sing” which first debuted on May 24th, 2019. Cody utilized his time with these individuals and honed in on his songwriting abilities which then led him to his next big achievement; reaching the semifinal round of Nashville Rising Song.
Cody’s passion for country music is heightened by the artists that he looks up to such as the immensely talented Chris Stapleton, Cody Jinks, and the wildly popular Luke Combs. However, Cody isn’t just a one trick pony, as he loves performing just about any genre of music and does so expertly. You can find Cody playing all over the great state of West Virginia and beyond by following all of his social media outlets and keeping up to date with his performance calendar.
As a West Virginia native, Cody works diligently to make his home state proud and succeeds in his efforts with every performance, every song, and every note.
2026 Howard County Fair
Contest Arena Events
(Included with Price of Admission)
Saturday – August 8th
3:00 pm 15th Annual Mule Jump
6:00 pm 48th Annual Horse Pull
Sunday – August 9th
11:00 am Antique Tractor Pull
Monday – August 10th
4:00, 6:00, & 8:00 pm “Outlaws & Peacemakers” (Wild West Re-enactment)
Tuesday – August 11th
6:00 pm 21st Annual Mule Pulling Contest
Wednesday – August 12th
6:30 pm Lawn Mower Contest
Thursday – August 13th
6:00 pm Skid Loader Contest
Saturday – August 15th
11:00 am Garden Tractor Pull
Peter Wood: Collector of the Impossible! (Magic Shows) (On the Entertainment Stage)
Shows on -
Sat.(8/2),Mon.,Wed.,Fri.: 11am, 12:30pm & 2pm
Sat.(8/9): 1, 2, & 3pm
Pony Rides (Lower Fair) -
Daily, Times TBD
Kids & Critters Barn (Barn 6) -
Daily, 9:30 am - 2 pm and 5 pm – 8:30 pm
Little Farmer's Barn -
Daily, 9 am – 6 pm
Agriculture Education Display (in Annex) -
Saturday (8/8) TBD – Opens after Judging
Sunday thru Saturday (8/15) 10 am - 9 pm
Butterfly Exhibit (Main Exhibition) -
Both Saturdays, Sun., Thurs., & Fri.: 10 am - 10 pm
Mon., Tues., & Wed. Noon - 10 pm
Antique Farm Machinery Display (beside Contest Arena) - Daily
Equine Exhibit (Horse Education Tent) - Daily, 2 pm-7 pm
Amusement Rides & Games
Both Saturdays and Sunday - 12 Noon - 11 pm
Monday thru Friday - 2 pm - 11 pm
Poultry & Rabbit Exhibit Buildings
Daily 8am – 9pm
Saturday (8/8) Rabbit Building closed until Noon
Children’s Entertainers – “Silly Willy” and “Hugs” - Daily
Beer, Wine, & Spirits Garden (in Main Exhibition Hall) -
Both Saturdays & Sunday: Noon – 10 pm
Monday thru Friday: 4 pm – 10 pm
Home Arts Exhibit Building
Saturday (8/8): Open 1 pm – 9 pm
Sunday thru Saturday (8/15): Open 10 am – 9 pm
Annex – (4-H, FFA, Farm & Garden Departments, & Ag. Education Exhibits)
Saturday (8/8): TBD (Opens after judging is completed) – 9 pm
Sunday thru Saturday (8/15): Open 10 am – 9 pm
Main Exhibition Hall – Vendors & Displays
Both Saturdays, Sunday, Thursday, & Friday: Open 10 am – 10 pm
Monday thru Wednesday: Open Noon to 10 pm
