It was the day of the Flying Derby and Maddie was so excited to watch it. But the family was running late due to the fact that Pippa took forever to find her Flying Derby crown. Dressing up is what she liked most about the competition. Maddie just liked the race itself as it was her favorite sport in the whole kingdom. Sarayah explained that Maddie used to use pretend to fly around the house with an old mop she used as a flying horse.

Maddie asked Primus if they could go faster as she didn't want to miss anything. Primus told the Coachman to take the high road instead. The high road was them flying all the way there. They arrived just in time to watch the race. The racers were let out and they took to the skies, avoiding every hurdle and doing anything they could to come in first place. While the race was going on, Starscream revealed to Maddie that their school had a flying derby team and that there was a try-out race next week.

He suggested that she could come and watch him and the others participate. Pippa was only going so she could see Prince Loki. He was the best rider in the whole school. Starscream argued that he was just as good as Loki. Out of the twins, Starscream was the better flier compared to his sister. But he never practiced enough on a flying horse to ever make it on the team. He was never allowed to fly on his own. It had to be on a horse.

But he promised that this year would be different. But back to the race. It was ending just as Starscream finished explaining and they had their winner. Maddie commented that it would be so much fun to ride in the Flying Derby. So, Pippa said that Maddie should watch the Flying Derby practice at school the next day. Maddie intended to.

So, the next day, Maddie, Pippa, and a few other Princesses went to watch the practice. Though Maddie was falling behind. Pippa greeted Prince Loki, wanting to wish him luck as she was his biggest fan. Loki thought that she must be if she came to watch the practice. Soon their coach, Gilliam, called all the Princes over to start. Maddie arrived just in time. Pippa tried leading her to the bleachers but Maddie went towards the Princes instead. 

"Good morning! Who's ready to race some flying horses?" Gilliam asked smiling as all the boys cheered

"Good morning, Sir Gilliam," Maddie said smiling

"Oh. Hello, Princess. The bleachers are right over there," Gilliam said pointing her in that direction

"I didn't come here to watch, Sir Gilliam, I came to try out for the team."

Everyone was taken aback by Maddie's request. 

"What... What's wrong?" Maddie was confused

"Um, only princes can ride in the Flying Derby," Loki told her

"So, princesses can't try out?"

Gilliam just started stumbling over his words trying to think of a response.

"But they don't," Pippa cut into the conversation, "The Flying Derby is just not a princess thing. There are many things princesses do like hosting balls and dancing too or wearing gowns of pink and purple that's what we like to do.'

'There are many things that princes like jousting, polo, and taking hikes,' Loki told Maddie, 'Suits of armor with lots of spikes that's what we really like.'

'We do princess things,' the Princesses told her

'And we do princely things,' The Princes told her

'And no one crosses in between,' both sides said, 'we stick to our routine.'

'But who knows what I could bring flying high upon a wing,' Maddie said smiling, 'I believe that anything can be a princess thing.'

Maddie got on the back of a wooden horse that the Princes used for practice, trying to prove everyone wrong.

'Read a poem,' Pippa told Maddie

'Or pick daffodils,' Princess Hildegard added

'Sing wistfully in window sills.'

Maddie fell off the horse and Gilliam caught her

'Derby calls for princely skills,' Gilliam told her

'It's not a proper princess kind of thrill,' Pippa said

'We do princess things.'

'And we do princely things.'

'And no one crosses in between,' Both sides said, 'we stick to our routine.'

'We climb trees and jump and swing,' Loki said to Maddie

'While we shop for royal bling,' the Princesses said

'So don't make a fuss, just stick with us,' Pippa said

'And do our princess things,' the Princesses said

Maddie left the crowd to be on her own for a moment.

'But who knows what I could bring flying high upon a wing. I believe that anything can be a princess thing.'

Maddie went home after school and told her animal friends about her day. Even bringing up the Flying Derby and how everyone was saying that only boys should be doing it. Lil' Ven hated that. He told Maddie that, if she wanted to do the Derby, then she should go and do it. Besides, there's a first time for everything. That gave Maddie a lot more confidence. So, at dinner, Maddie announced that she would be trying out for the Flying Derby team.

Pippa reminded her that it was a Prince thing, not a Princess thing. Maddie just argued that there was a first time for everything. Sarayah thought it was a wonderful idea and Primus almost hesitantly agreed. Starscream argued that Maddie knew nothing about the Derby or how to ride a horse. So, Primus told him that he could teach her. But even Starscream was against that idea. He was worried about what the other Princes would say about it.

Pippa commented that they would be too busy laughing to say anything. But Sarayah said that they would all say what a great brother he was for helping Maddie. Primus even added that it would also give Starscream more time to practice too. Starscream kept trying to make excuses saying that Maddie didn't even have riding clothes. Bruno spoke up saying that she would by morning. So, it was settled. Maddie would practice for the tryouts with Starscream helping her.

So, Maddie arrived with Starscream in her new riding clothes, ready to practice. She said hello to Gilliam, saying that she was ready for practice but she still needed a horse. Gilliam explained that there was only one horse left but no one wanted him. Maddie said that she did. So, they went into the stables to meet him. There was another rider with a horse that Maddie thought was hers until it moved out of the way, revealing a smaller horse.

Barely even pony. His name was Dusk. Maddie walked over to Dusk and introduced herself. Dusk shyly said hello back. Maddie asked if he would be her horse for the Flying Derby. Dusk started to go on about how Maddie didn't want him as her horse for the Derby. But he didn't expect her to understand as she couldn't speak horse. But Maddie revealed that she could understand him thanks to her Amulet.

Now that he knew she could understand, Dusk went on more about how she should pick another horse because he had short legs, small wings, he wasn't a fast flier, and he worries about everything. Maddie thought he was perfect. The trumpets went off, telling everyone that it was time for practice. Everyone met at the track, ready to practice. Gilliam reminded them that the tryout race is at the end of the week and explained the rules; Only the first two riders to pass the finish line would make the team.

So, they had to practice hard, fly fast, and always be royal. Maddie struggled to get on Dusk's back. Starscream noticed and helped her on. Seeing this, Loki teased him, telling him to help his sister get on her pony when he was done. Annoyed, Starscream lead his and Maddie's horse to somewhere else for practice.

Now that they were away from the other Princes, Starscream started to teach Maddie how to ride a horse. Starscream made it sound so easy but, when Maddie tried, she kept falling off Dusk's back. Thankfully there was padding that broke her fall every time she fell. But Maddie never gave up. She continued to get on Dusk's back and try again. And every time she would fall off. 

"What am I doing wrong?" Maddie asked Starscream after falling again

"I don't know. We can stop if you want," Starscream offered

"I am not giving up. I don't care how many times I fall. I am going to try out for the team."

"You gotta stay on your horse first," Loki said landing in front of them, "I know you were an amazing flier, Starscream, but you're a horrible racer on a flying horse, and a worse teacher. I guess Flying Derby isn't a princess thing after all."

Starscream spread his wings and flew up to Loki's height on his horse, "You can make fun of me all you want, Loki, but not my sister."

Loki just laughed and left the two alone. Starscream returned to the ground.

"If you're not going to give up, I won't either," Starscream told Maddie.

They shared a fist bump before Starscream decided to try a new teaching method. After getting up onto his horse, he left Maddie up and decided to show her what to do. Starscream got his horse into the air and continued to show Maddie what to do. From down on the ground, Hildegard noticed Maddie in the air with Starscream. She asked Pippa if that was really Maddie up there and she confirmed that it was.

But she couldn't believe that Maddie was really doing this. And neither could Maddie but she was happy about it. Afterward, Starscream started to teach Maddie how to race. Maddie was doing great for the most part. Until they reached the last hurdle. Under a gate and through the steeple. The gate was easy, but Dusk couldn't make it to the top of the steeple and flew back down. The only good part about it all was Starscream got his fastest run ever.

But he was more concerned about Maddie. He went over to her and Dusk, saying that she would get it next time. Maddie could only hope. When they all got home for the day, Pippa checked up on Maddie about what had happened. She saw that Dusk couldn't make it. Maddie just said she needed more practice. Pippa reminded her that she only had one day left until the race and that maybe Princes were just better at this. She advised Maddie to stop as she didn't want her sister to get hurt. Pippa left and Maddie walked into her room

"So, uh, how'd it go?" Lil' Vent asked

"Lousy," Maddie said, "I can't even make it to the finish line, and I only have one more day before the race. Pippa said I should quit. I don't know what to do."

"My mother had a saying. 'The early bird gets the worm.'," Robin told Maddie

"What does Maddie need a worm for?" Mia, a bluebird, asked

"She doesn't, Mia," Lil' Vent said, "Hey, what Robin is trying to say is, get an early start tomorrow. You've got one more day, Maddie. Make it count!"

"Good idea. Thanks, guys," Maddie said smiling.

So, Maddie got to school early the next morning to practice before the race the next day. For the whole day, Maddie and Dusk would run the course until they got it right. The only thing they still struggled on was the Steeple. Dusk just couldn't make it to the top without falling back down. Yes, he caught them both before he crashed but he just couldn't make it. Dusk kept blaming himself for messing it up and telling Maddie that she needed a bigger horse. Maddie would assure him that he was big enough.

So Dusk corrected himself to a faster horse. Maddie reassured him again that he was fast enough too. Loki noticed Maddie comforting Dusk and decided to comment. He told her that she could talk to dusk all she wanted, but it wouldn't help her get through the steeple. And if she couldn't even finish the race, why bother starting it? He left while commenting that Maddie should go back to the other Princesses, where she belonged. Maddie was considering it at this point. Loki was right and Maddie knew it. She returned home, feeling down about the whole thing. Sarayah was there to greet her when she came back. 

"Mom, what are you doing out here?" Maddie asked sitting with her mother

"Waiting for you," Sarayah said smiling, "Wow, you've been practicing all this time?"

"Uh-huh."

"Well, I have some good news. Your father and I are coming to the try-out race tomorrow."

"Oh! You don't have to do that!"

"Oh, we wouldn't miss it for the world."

"It's just that, I'm thinking about not going."

"Why?"

"I still can't make it through the last steeple. Maybe Loki and Pippa are right, and only princes should race."

"And maybe a princess can do anything a prince does if she keeps trying and never gives up."

"Do you think I can make the team?"

"I know you can, Maddie. But what's important is what you think."

The next day, Maddie did join the race. She wanted to at least try to make the team. But there were a lot of people here to watch, making Maddie nervous. Pippa just acted like it was normal while being happy that she wore her Flying Derby Tiara. Loki walked past and Pippa went to wish him luck. Starscream approached Maddie, asking if she was ready for this. Maddie was more concerned as to why there were so many people there.

Starscream explained that everyone wanted to know if a Princess could make the team. And Starscream was more than confident to help Maddie show everyone that she could. So, Maddie and Starscream mounted their horses and made their way to the starting line. Maddie was in between Starscream and Loki. Loki was annoyed that Maddie didn't take his advice and scoffed. The Fairies flew above the competitors, ready to begin the race

"Welcome to the Flying Derby try-out race," Flora said to the crowd, "As everyone knows, the first two riders to cross the finish line earn their place on royal preps Flying Derby team! So without further ado, horses on your wigs."

"Get set," Fauna said

"Go!"

And they were off! All of the horses ran ahead of Dusk and took the lead while Dusk struggled to get off the ground. But he soon managed and started to catch up to the other racers. Loki took an early lead with Starscream just behind him. Pippa cheered Loki on as they went through their first hurdle. But soon Maddie started making her way through the pack, catching up with Starscream. As they passed their third hurdle, Loki purposely halted his horse, startling Dusk enough to throw Maddie off his back.

Pippa saw this happen and was more than upset with Loki for doing this. Loki just bid her goodbye and continued the race. Pippa booed Loki for what he did while Dusk checked on Maddie. Starscream flew over, telling Maddie to get back on Dusk. Maddie asked what the point was since she already blew it. But she told him to keep going as he could still win. Starscream told her that she could too and that he wasn't crossing the finish line without her.

Starscream helped Maddie back on Dusk's back and they left to catch up. Maddie and Starscream caught up to the pack and passed them. But Loki still had the lead. Maddie and Starscream were just behind Loki. But in front of them was the steeple. Dusk was still unsure about that part of the race but Maddie had hopes that he could do it. So, they passed under the gate and started to climb the steeple.

And, surprisingly enough, Dusk actually made it up, allowing Maddie to ring the steeple bell. Loki looked back, watching Maddie and Dusk finally make it over the top. He was so surprised that he almost didn't see that he was going off-course into some trees. He got back on track and started racing towards the finish line. As they turned down the stretch, it was Loki, Starscream, and Maddie neck and neck.

It was a close call, but Maddie and Starscream passed Loki, crossing the finish line together, and leaving Loki in the dust. Everyone cheered for the two. They were joining the Flying Derby team. Realising this, Dusk started to freak out at the fact that they would have to race more and had to lie down. Maddie only laughed at his silliness. Starscream walked up to Maddie and she hugged him, thanking him for helping as she couldn't have done it without her.

Starscream hanked her too. If it weren't for him teaching her, he would've never had enough practice to win this race. Gilliam approached them, handing them both their official team jerseys. The two accepted them and put them on. Sarayah and Primus approached the two, congratulating them on their win. Pipp walked over to a disappointed Loki. But, knowing that he still had a fan, he acted all nice to her. But Pippa ignored him and walked over to her siblings instead. Pippa was no longer his fan.

"You were great, Maddie," Pippa said smiling and hugging her, "I was wrong. Flying Derby is a princess thing."

"Anything can be if we try hard enough," Maddie told her smiling

They pulled away from the hug and Pippa looked at the new jersey.

"That's what they gave you for winning?" Pippa asked, "Oh, no. You need a real prize," Pippa thought to herself, "I know."

Pippa took her tiara off.

"But that's your Derby tiara," Maddie said

"I want you to have it," Pippa said putting it on Maddie's head, taking her riding helmet from her, "Because I'm your biggest fan."

"You know, I won, too," Starscream spoke up

Pippa put Maddie's helmet on, "I know."

The tree smiled at each other while Maddie petted Dusk. Maybe Prince things can be Princess things too.