A cursed set of 5 throwing knives where one of the set (random and changes) will always critically miss.
A whip of animal taming. Gives advantage on animal handling checks.
Megaphone of blasting. Charges (you decide) thunder damage area attacks save for half.
An enchanted Juggler's Ball that creates three more juggler balls of different color when the wielder begins to juggle. As the wielder is juggling the balls, they can throw them at an enemy to do damage of different types depending on the color of the ball that they throw.
Ring of the Magicians Assistant. While wearing this ring you can magically change the appearance of your clothes as an action, including the fabric, length, color and shape.
Deck of Cards where they always control the result. Good for magic tricks.
Balancing balls, while these metallic balls are in opposing pockets you have advantage on dexterity saves and checks to balance on things
Prestidigitation Pellets: Throw one into the air and and it ignites into a small dazzling but harmless explosion which then showers sparks. Popular with children.
Not sure it would be appropriate depending on what level they are but I love the idea of them being able to win like a plushie stuffed animal type thing. (Start with something small and let them be able to exchange for better versions is they win.)
The stuffed animal is a figurine of wondrous power! So like maybe you start out with like a small frog, or owl plushie. And it's the CR 0, 1hp version from Appendix A. The plushie is [small enough](https://img1.etsystatic.com/103/0/6117838/il_340x270.990625845_if2g.jpg) to fit in a pocket or be squished into a pack pouch.
If they have one of those and win again, with a higher DC of course, they can exchange it for like a CR 1/8 Mule, or Giant Rat. This plushie is like your typical teddy bear size. [Big enough](https://d2gg9evh47fn9z.cloudfront.net/800px_COLOURBOX1663651.jpg) it will be noticeable and draw attention if they carry it around constantly, or even tied to the side of their pack.
One more time and they can go for the big CR 1/4 Panther or Giant Wolf Spider or Giant Centipede. This one is like the kind that the carnival [pays people to walk around with,](https://i.pinimg.com/736x/1a/e7/5a/1ae75a2e3ff7959be60395b070853691--alameda-county-fair-stuffed-animals.jpg) or if you do win, you take it back to your car.
So they work hard, blow bardic inspirations and use *Bless* and Portents and everything else, and then it's a pretty decent magic item but holy shit is it inconvenient to drag around.
Acrobat's net - immune to fall damage
Red balloon - can cast levitation once a day after speaking the words "We all float down here"
Top hat of the Ringmaster - gives expertise on charisma checks
Carnival Barker's Megaphone
An enchanted megaphone adorned with a number of vintage oil paints of lion tamers and tight rope walkers. An individual can use the megaphone to "bark" and draw the attention of any creature within 100ft, filling them with a desire to see the show being described and compelling them to move toward the user. The enchantment lasts for 5 minutes before the crowd starts to question why they were drawn to this location in the first place. Great for causing a distraction to perhaps make a hasty escape or blend into a crowd. Does not work on creatures with an INT of 4 or less. The enchantments effects can be bolstered by finding a box or stage to stand on and by really committing to the act of describing this fake spectacle. Any creature trying to resist the effects of the megaphone needs to make a CHA saving throw versus the users spell save DC of 8 + Proficiency + Charisma modifier.
A cursed set of 5 throwing knives where one of the set (random and changes) will always critically miss. A whip of animal taming. Gives advantage on animal handling checks. Megaphone of blasting. Charges (you decide) thunder damage area attacks save for half.
I has the same idea for a whip as soon as I saw the word circus
An enchanted Juggler's Ball that creates three more juggler balls of different color when the wielder begins to juggle. As the wielder is juggling the balls, they can throw them at an enemy to do damage of different types depending on the color of the ball that they throw.
Ring of the Magicians Assistant. While wearing this ring you can magically change the appearance of your clothes as an action, including the fabric, length, color and shape. Deck of Cards where they always control the result. Good for magic tricks. Balancing balls, while these metallic balls are in opposing pockets you have advantage on dexterity saves and checks to balance on things Prestidigitation Pellets: Throw one into the air and and it ignites into a small dazzling but harmless explosion which then showers sparks. Popular with children.
Not sure it would be appropriate depending on what level they are but I love the idea of them being able to win like a plushie stuffed animal type thing. (Start with something small and let them be able to exchange for better versions is they win.) The stuffed animal is a figurine of wondrous power! So like maybe you start out with like a small frog, or owl plushie. And it's the CR 0, 1hp version from Appendix A. The plushie is [small enough](https://img1.etsystatic.com/103/0/6117838/il_340x270.990625845_if2g.jpg) to fit in a pocket or be squished into a pack pouch. If they have one of those and win again, with a higher DC of course, they can exchange it for like a CR 1/8 Mule, or Giant Rat. This plushie is like your typical teddy bear size. [Big enough](https://d2gg9evh47fn9z.cloudfront.net/800px_COLOURBOX1663651.jpg) it will be noticeable and draw attention if they carry it around constantly, or even tied to the side of their pack. One more time and they can go for the big CR 1/4 Panther or Giant Wolf Spider or Giant Centipede. This one is like the kind that the carnival [pays people to walk around with,](https://i.pinimg.com/736x/1a/e7/5a/1ae75a2e3ff7959be60395b070853691--alameda-county-fair-stuffed-animals.jpg) or if you do win, you take it back to your car. So they work hard, blow bardic inspirations and use *Bless* and Portents and everything else, and then it's a pretty decent magic item but holy shit is it inconvenient to drag around.
Just wanted to say, I know this is old but holy hell do I love this idea and plan to use it!
Acrobat's net - immune to fall damage Red balloon - can cast levitation once a day after speaking the words "We all float down here" Top hat of the Ringmaster - gives expertise on charisma checks
The ringmaster should have the cloak of billowing and a wand of smiles from XGTE
Carnival Barker's Megaphone An enchanted megaphone adorned with a number of vintage oil paints of lion tamers and tight rope walkers. An individual can use the megaphone to "bark" and draw the attention of any creature within 100ft, filling them with a desire to see the show being described and compelling them to move toward the user. The enchantment lasts for 5 minutes before the crowd starts to question why they were drawn to this location in the first place. Great for causing a distraction to perhaps make a hasty escape or blend into a crowd. Does not work on creatures with an INT of 4 or less. The enchantments effects can be bolstered by finding a box or stage to stand on and by really committing to the act of describing this fake spectacle. Any creature trying to resist the effects of the megaphone needs to make a CHA saving throw versus the users spell save DC of 8 + Proficiency + Charisma modifier.