It was Halloween in the two worlds and Gwen was preparing a celebration at her parent's house. She magically creates Halloween decorations and prepares the food, drinks and candy. In their backyard and inside the house. Edgar and Margarine look around and are impressed with the decorations.
"Wow, dear. This looks great." Margarine complimented.
"Yes. Just remember to clear everything up after the party tonight." Edgar reminded her.
"Yes, papa. I will." Gwen answered.
Her fiancé Clarence and her cousin Virgil dressed as the Mad Hatter entered the backyard carrying some Halloween games accessories.
"We got the games honey." Clarence said.
"Where do you want these?" Virgil asked.
"Just place them over on that table. Thanks guys." Gwen said and thanked.
Both men placed the games on the table.
"Thanks for helping me out." Clarence thanked Virgil.
"No problem, Clarence. You will soon be part of the family. And thank you for making me a groomsman with the cups." Virgil thanked.
"Yeah. You deserve it, Virgil. You saved me and Gwen." Clarence said.
Virgil smiled at Clarence, forming a bond between them. Just then, Clarence's half-sister Cordelia dressed as Alice in Wonderland jumped on Virgil's back.
"Hey sweetheart!" Cordelia greeted.
"Hello dear." Virgil said.
"And hey brother!" Cordelia greeted Clarence.
"Hey Cordelia. How are things going now that you two are dating?" Clarence asked.
"It's going great! We really are connecting." Cordelia said as she gives Virgil a kiss on his cheek.
Vigil blushed a little as Cordelia got off his back.
"Hey Cordelia. Did you get the Halloween piñata?" Gwen asked.
"You know it sugar!" Cordelia said as she held up a jack-o-lantern shaped piñata.
"Great! You can hang it on that tree branch. The cups and my younger cousins love hitting the piñata for candy." Gwen said.
Cordelia gets to work tying the piñata on the tree branch and sets up the blindfold and baseball bat.
Just then, Rose and William arrive with their children Emma and Jack. Rose was dressed up as Wendy and William was dressed as Peter Pan.
"Hey sis!" Gwen greeted.
"Hey Gwen!" Rose called back.
Both sisters hug each other. Then Virgil joins them and lifts them up in his big arms.
"Hey Virgil." Rose weakly said.
"Hey Cousin Rose." Virgil greeted.
He places both sisters down.
"Glad you could come. You, William and the kids." Gwen said.
"Yes. It'll be their first Halloween. Check out their costumes." Rose said as she showed her the twins.
Emma and Jack were dressed in a rabbit and fox costume.
"Aww, you two look so cute as Lost Children!" Gwen complimented.
"Thanks, it was my idea." William bragged.
Then, Gwen's younger cousins Hailey and Kailey arrived at the party both dressed like a fairy and a witch.
"Hey Gwen! Hey Rose!" Hailey and Kailey called.
"Hey girls!" Gwen said as she hugged the twins.
"We're ready for the party!" Hailey said.
"Yeah! When does it start?" Kailey asked.
"It'll start in a few minutes; we're just waiting for the rest of our guests to arrive as we get everything ready." Gwen answered.
Just then, they hear three familiar voices calling from the door portal.
"Hey everybody!"
They all turned to see Cuphead, Mugman and Ms. Chalice dressed up as a Devil, Mugbeard and a goddess as they entered with Elder Kettle right behind them.
"Hey fellas!" Gwen said as they all hugged Gwen.
"Let's get this party started!" Cuphead said excitedly.
"Yeah! This'll be fun!" Mugman agreed.
"And we wanna go trick-or-treating in the human world this year!" Ms. Chalice added.
"Patience guys. You guys will get to go with Hailey, Kailey, Emma and Jack this year. William is gonna take you guys." Gwen explained.
"Yay!" All three cups cheered.
"Oh wait! I almost forgot. Clarence, come here!" Gwen called.
"Yes love?" Clarence asked.
Gwen got out her magic pen and magically transformed her outfit into a big pink ballgown with a tiara and Clarence's outfit into an emerald-green tuxedo with a top hat.
"Oh wow. I'm the Wizard of Oz and you're Glinda." Clarence said, figuring it out.
"Yep. I'm like the good witch around here." Gwen bragged.
After finishing up the party decorations, the rest of the party guests Kizzy Thompson along with her boyfriend Isaiah Turner, Akilah Jassim, Elijah Rosenberg, Evelyn Harris and Shirley Miller arrive and socialize with each other.
After a while, Gwen gathered everyone and started the party games. First, they started with a spoon relay race with fake eyeballs with the cups winning. Next, they have an apple bobbing game in separate buckets, which Virgil wins with the most apples bobbed. Next, they set up bowling pins and play pumpkin bowling. Kizzy wins the game with her incredible skills along with Isaiah. Next, they play a sack race game with the sacks resembling ghosts. Hailey and Kailey win the race. Next, they play musical chairs with Elder Kettle's radio to help with the music. Elijah wins the game with his quick moves.
It was time for the piñata game and the cups and the twins line up. Mugman goes first and takes the first swing, but only hit it barely. Ms. Chalice goes next and make a better hit. Hailey and Kailey take their turns and the piñata started to break. Cuphead goes up last and delivered a final blow, making the candy drop everywhere.
"Yep, I still got it." Cuphead bragged as he collected some candy.
"Still don't overthink it, do you?" Mugman asked.
"Nope." Cuphead answered.
After a while of games and fun, William decided it was time to take the kids trick-or-treating.
"Alright kids, you ready to go get some candy?" William asked.
"Yeah! Yeah! Yeah!" All three cups said.
"Yeah!" Hailey and Kailey agreed.
The five kids each grab a pumpkin bag to hold candy and prepare to leave with William and the infant twins.
"You guys be careful and don't stay out too late." Rose reminded them.
"We will!" All the kids called.
Rose takes Ms. Chalice aside.
"Chalice, remember what we discussed?" Rose asked.
"No turning into a ghost. No charming and scamming people for free stuff. And no stealing wallets." Ms. Chalice answered.
"Correct. Now go have fun." Rose said, feeling relieved.
Ms. Chalice joins the group tap-dancing, making Rose shake her head.
William takes the children and start going around the neighborhood to houses. They start with the first house and Cuphead knocks as the five kids waited. A lady answers the door with a bowl of candy.
"Trick-or-treat!" All five kids called.
"Aw, what cute costumes! Here's some candy!" The lady said as the five kids took some candy and filled their bags.
Ms. Chalice tempted to swipe some more candy.
"Ahem!" William cleared his throat.
Ms. Chalice turned around and smiled nervously.
"Don't even think about it." William warned her.
"Aw, ya got me Will. Heh heh." Ms. Chalice said nervously.
"Come on kids, let's go." William said as he pushed the stroller with Emma and Jack.
The kids go with William around the neighborhood and collect more candy.
Meanwhile, the Devil along with Henchman appear in the human world and notice a lot of children in costumes going trick-or-treating.
"Ah, look at all these human children dressed as something they're not and getting free candy from random stranger's houses." The Devil said.
"Duh, yeah boss. It's Halloween. The one day of the year kids dress up and go get candy." Henchman answered.
"And a wonderful time to make these brats very scared." The Devil said evilly, having an evil plan.
Henchman smiled as the Devil got to work using his pitchfork to scare kids. One trick-or-treater in a ghost costume passes Henchman and says,
"Nice costume."
"Oh, heh heh. Why thank you." Henchman said, pretending to go along with it.
"Where's your candy bag?" The kid asked.
"Oh um…" Henchman nervously answered.
"Here, I have an extra one. Do you want it?" The kid asked handing an empty candy bag.
"D'aaww, thank you. That's very kind of you." Henchman thanked as he took the bag.
"Bye!" The kid said and left.
Henchman decided to go to several houses to get some candy, posing as a trick-or-treater. While he does that, the Devil continues scaring kids with his monstrous transformations and scary roaring. After scaring a large group of kids, he laughs happily as he meets up with Henchman who returns with a large bag full of candy.
"Duh, how was it boss?" Henchman asked as he ate a chocolate bar.
"Oh, it was great! The screams, the looks on those brats faces and them running away. I've never felt so wicked in my life!" The Devil said happily.
"Duh, that's great boss! I had some fun too! Humans believe we're in costumes like all these kids and I got free candy!" Henchman said as he licked a lollipop.
"Give me a candy!" The Devil said and snagged a chocolate candy and ate it.
"So, boss, what do ya wanna do now?" Henchman asked.
"I heard through the grapevine that my beautiful flower's hosting a Halloween party at her parents' house and all her human friends are gonna be there." The Devil answered.
Henchman gasped.
"B-b-b-but boss! We're not invited!" Henchman protested.
"Oh, I know we're not. Which is why we're going to… crash it." The Devil said evilly.
"Aw jeez." Henchman said worryingly.
Back at the Emmons residence, everybody is having a good time at the Halloween party with all the guests socializing. Elder Kettle got a little tired and fell asleep in one of the recliners in the house while Margarine passed out candy to trick-or-treaters.
Gwen along with her friends and sister sit around a firepit sipping apple cider.
"So, how's life going for you Kizzy?" Rose asked.
"Oh, it is great! Isaiah and I still workin' at the middle school, we're exercising together and he's helping me train for the next Olympic games." Kizzy said.
"Yeah. I've been getting' a lil' stronger with her." Isaiah admitted.
"Good for you." Clarence complimented.
"Thanks." Isaiah thanked.
"How about you Evelyn? How's the fabric shop?" Gwen asked Evelyn.
"Oh, it's incredible. Mrs. White has me teaching knitting classes for people twice a week and business has been great." Evelyn answered.
"Wonderful. And you Shirley?" Gwen asked Shirley.
"It's great. Mama says she's been so proud of me since I got that job at Mr. Harris's oil business as the receptionist. Maybe one day, I'll pursue singing like her." Shirley said.
"Yeah, I'm glad daddy hired you to work for him." Evelyn said.
"That's wonderful you two." Akilah complimented.
"Thanks, so what do you do?" Evelyn asked Akilah.
"I work for Gwen as her assistant at her art studio. And she lets me make and sell my fashion too." Akilah answered.
"Aw that's great." Shirley complimented.
"How about you… uh, Elijah was it?" Isaiah asked.
"Yes. I run my own music shop and sell instruments and music supplies." Elijah answered.
"Aw that nice." Cordelia complimented.
"Yes, your parents would've been very proud of you." Virgil said.
"Thank you." Elijah thanked Virgil.
Just then, William along with his kids, the cups, Hailey and Kailey return from trick-or-treating. Hailey and Kailey's parents Mildred and George come by the house and pick up their daughters. They say goodbye to everyone and leave with their parents and return home.
William settles his children down for bedtime in their stroller and joins his wife at the firepit. Elder Kettle wakes up from his nap and takes the three cups back to the cottage through the door portal.
"Well, this has been fun, but I think I'm ready to call it a night." Rose said, feeling tired.
"Yeah, me too. We gotta get ready for work in the morning." Kizzy said as she and Isaiah get up.
Everyone gets up, ready to leave as Gwen prepares to clean up the party. But before anyone could leave, the lights suddenly go out.
"What the? The power's out?" Gwen asked.
"Weird, I'll check the fuse box. Fuse must be out." William said.
Suddenly they hear a familiar evil laugh echo through the backyard.
"Gwen? I think we got a party crasher." Clarence said worryingly.
"Oh no… he's here!" Gwen exclaimed.
The group of humans gasped as they notice the Devil making a grand entrance from the sky with a spotlight shone on him. The Devil casually approaches the humans as they looked at him in horror.
"Happy Halloween my good humans. I heard there was a party going on. So, I thought I'd crash it." The Devil taunted.
Meanwhile, Henchman was gathering a plate of food and desserts.
"Look Big D, party's over! Get out!" Kizzy bravely said.
"Ah, Kiz-kat. I see you haven't changed since we last met. I see you have a boyfriend now." The Devil said as he noticed Isaiah shaking with fear.
Kizzy attempted to punch the Devil in his nose, but he quickly stopped her.
"Woah there. I don't need you breaking my nose again." The Devil sternly said.
He releases Kizzy's hand and moves on to Rose and William.
"Well, well, well. I see you two are still together despite your problems. And your little ones are growing up. How cute." The Devil taunted as he noticed Emma and Jack.
William steps in front of his children, ready to protect them.
"Don't you dare come near them ever again!" Rose angrily warned.
"Fine. Whatever Rosy Cheeks." The Devil impatiently said.
Next, he moved onto Akilah and Elijah.
"Well, Akilah. I see you're dating your childhood sweetheart now. A poor orphan boy whose home has been destroyed recently?" The Devil asked tauntingly.
Akilah slapped the Devil's hand.
"Leave him alone Iblis!" Akilah angrily yelled.
"I didn't bring him into this. You did my dear." The Devil pointed out.
Next, he moves on to Evelyn and Shirley who looked at him in horror.
"Ah, you two again. You two are friends with Gwen now I see? Turned against that annoying, self-absorbed, crazy ninny?" The Devil asked.
"Gwen saved us, so we owe her big time!" Evelyn said.
"Yeah, we wouldn't be standing here if it weren't for her!" Shirley added.
"Ugh. Of course." The Devil grumbled, remembering he lost to her in a game of hide-and-seek.
Next, he moved on to Cordelia and Virgil.
"Ah, my old dance partner. I see your dating that big oaf who nearly broke all my bones." The Devil said, noticing they are together now.
"We are not dance partners! You tricked me!" Cordelia snapped.
Virgil stepped in front of Cordelia, ready to protect her.
"If you don't want a round two, you will leave this place at once." Virgil warned.
"Well, I would but I'm not finished yet." The Devil said.
Finally, he turned his attention to Gwen and Clarence.
"Ah, my beautiful flower. You look lovely in that beautiful good witch costume." The Devil complimented.
Gwen said nothing as Clarence held Gwen, protecting her.
"And then there's you. The no-account street urchin who dares steal my fiancée from me." The Devil said angrily.
Clarence glared at the Devil for his insult.
"Anyway, I'll just take you away my dear. Now, come along." The Devil said as he prepared to take her hand.
But before he could, the Devil felt something hit him very hard on his back.
"OOOOWWWW!" The Devil cried in pain.
It is revealed that Isaiah took the baseball bat from the piñata game and whacked the Devil in the back with it. The Devil weakly got up and glared at Isaiah.
"You're going to wish you haven't done that!" The Devil angrily said as he prepared to attack.
"Uh oh." Isaiah said worryingly.
But suddenly, the Devil finds himself trapped in a bubble. He turned around and saw Gwen used her ink pen to stop the Devil.
"Gwen! Why you…!" The Devil angrily said.
"Sounds like someone needs to go home." Gwen said.
Gwen magically made a door portal to Inkwell Hell appear as the bubble electrocuted the Devil severely.
"Now, click your heels three times and say, 'There's no place like home.'" Gwen said tauntingly.
Then, she cast the Devil through the door portal with Henchman running after his boss with a plateful of food and his candy bag. Gwen closed the door portal and magically made it disappear. Everybody cheered for Gwen as Clarence gave her a kiss.
"That was amazing boss!" Akilah complimented.
"Yeah girl! You taught that no-good vermin a lesson!" Kizzy added.
"You did very well Gwen. We are proud of you." Virgil said.
"Aw thanks everyone." Gwen said as she magically cleared all the Halloween decorations as the power came back on.
After saying goodbye to everyone. Gwen, Clarence, Cordelia, Akilah and Elijah all return back to their homes in the Inkwell Isles and went straight to bed.
The next day, Gwen and Clarence meet up after breakfast at the Emmons house to continue the wedding planning.
"That was a fun party last night love. Even when the Devil showed up again." Clarence complimented.
"Aw, thanks. I had fun too. And I thought our costumes were very clever, don't you think? I could've done better than Glinda and told Dorothy she could've gone home with those ruby slippers instead of endangering her with them." Gwen said.
"Oh yeah. And that so-called wizard was so fake. I could've done better too. Ahem, 'I am Oz, the great and powerful! The great Oz has spoken! Pay no attention to the man behind the curtain!'" Clarence imitated the wizard.
Gwen laughed at Clarence.
"Good one honey." Gwen complimented.
"Why, thank you. Maybe I should get into the acting business." Clarence said.
"Oh yeah? 'Are you a good witch or a bad witch? Only bad witches are ugly. Oh, rubbish! You have no power here. Begone, before somebody drops a house on you too!'" Gwen imitated Glinda.
Clarence laughed at Gwen.
"Nice!" Clarence complimented.
"Thank you. I learned a lot from Sally Stageplay." Gwen bragged.
"That's great." Clarence said.
"All Dorothy had to do was follow the yellow brick road with those munchkins singing." Gwen said.
"Follow the yellow brick road to the Emerald City." Clarence said in a cartoony-like voice.
Gwen snickered and continued looking at the wedding papers.
"Follow the yellow brick road." Clarence said in a lower voice.
Gwen gave Clarence an unamused stare.
"Follow the yellow brick road." Clarence said in a girl-like high pitch voice.
"Okay, now you're just being annoying." Gwen said.
"Follow the yellow brick…" Clarence said in another funny voice until Gwen got out her ink pen and magically made Clarence stop talking.
"One more 'follow the yellow brick road' and I'll drop a house on you!" Gwen warned.
Clarence nodded fearfully in agreement.
"Good!" Gwen said and released his mouth.
Both Gwen and Clarence resume their planning for the wedding.
Back at the cottage, Cuphead eats most of his Halloween candy while Mugman secretly hid his bag of candy in a new hiding spot since he knew he couldn't trust Cuphead with his secrets. Ms. Chalice appeared in the cups' room, inviting them to play outside, which they accept and join her.
After a while of making wedding arrangements, Gwen and Clarence head back to the cottage and join the cups outside. They all have fun together until they all lay on the grass and look up at the sky.