Wacky Runs

Santa suits, pizza stops, doughnuts, midnight fireworks — the themed fun runs of New Jersey, New York, Pennsylvania & Florida, in one place. Every listing links out to the official race site to register.

Cupid's Undie Run

Cupid's Undie Run has 4 upcoming themed fun runs. Next up: Cupid's Undie Run — Greater Philadelphia on Sat, Feb 27, 2027, Cupid's Undie Run — Pittsburgh on Sat, Feb 27, 2027, Cupid's Undie Run – Orlando on Feb 2027 — date TBA. Cupid's Undie Run is a charity run in your underwear — brave the cold for a good cause. Editions below run from Philadelphia to Orlando, each with its own venue and registration. Across Florida, New York and Pennsylvania. Themes on this page: Undie. Venues: Cupid's Undie Run — Greater Philadelphia at Stateside Live!, 1100 Pattison Ave; Cupid's Undie Run — Pittsburgh at McFadden's, 211 North Shore Drive. Every listing links out to the official race site to register.

Feb 2027 — date TBA
Orlando (Downtown Orlando; 2027 venue TBA), FL
~1 mile
The wacky bitDrinking and dancing, then a mile(ish) jog in your underwear, then an epic dance party — raising money for the Children's Tumor Foundation.
Price
See official site (2027 registration not open yet)
Medal
Not listed
Shirt / swag
Not listed
Race details →Register on official site →

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Frequently asked questions

How many cupid's undie run are listed?

4 upcoming cupid's undie run are listed on this page.

What is the next one?

Cupid's Undie Run — Greater Philadelphia on Sat, Feb 27, 2027 in Philadelphia, PA.

Where are they?

Florida, New York and Pennsylvania — in Manhattan, Orlando, Philadelphia, Pittsburgh.