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.

Pittsburgh

Pittsburgh has 5 upcoming themed fun runs. Next up: 2026 Jingle Bell Run — Pittsburgh on Sat, Dec 5, 2026, Ugly Sweater Beer Run x Cinderlands on Sat, Dec 12, 2026, The Christmas Eve 5K on Thu, Dec 24, 2026. Pittsburgh's wacky calendar runs from a Jingle Bell run on the North Shore to an ugly sweater beer run in the Strip District and a Christmas Eve 5K. Everything here is in Pittsburgh. The calendar runs from Dec 5, 2026 to Feb 27, 2027. All in Pennsylvania. Themes on this page: Costumes, Food, Santa & Christmas, Undie, Valentine's. Venues: 2026 Jingle Bell Run — Pittsburgh at 211 North Shore Drive; Ugly Sweater Beer Run x Cinderlands at Cinderlands Warehouse, Strip District. Every listing links out to the official race site to register.

2026 Jingle Bell Run — Pittsburgh

Santa & Christmas

Sat, Dec 5, 2026 · 8:30 AM

Pittsburgh (211 North Shore Drive), PA

5K / 1 Mile / Kids Run

The wacky bitStrap on the jingle bells and run the North Shore in full Santa gear for the Arthritis Foundation.

Price: 5K $45.00 + $3.70 SignUp fee · 1 Mile $40.00 + $3.40 · Kids Run $25.00 + $2.50
Medal: Yes
Shirt / swag: Yes

Race details →Register on official site →

Ugly Sweater Beer Run x Cinderlands

Sat, Dec 12, 2026 · 11:00 AM

Pittsburgh (Cinderlands Warehouse, Strip District), PA

~5K

The wacky bitRun about 3.1 miles in your ugliest Christmas sweater, finish at the brewery, and trade the effort for a craft beer and a pint glass.

Price: From $41.83
Medal: Not listed
Shirt / swag: Not listed

Race details →Register on official site →

The Christmas Eve 5K

Santa & Christmas

Thu, Dec 24, 2026 · 10:00 AM

Pittsburgh (W. General Robinson St, North Shore), PA

Price rises Nov 18

5K

The wacky bitYes, an actual Christmas Eve morning 5K on the North Shore — earn the eggnog before the day even starts.

Price: $35.00 + $4.60 SignUp fee · Ages 4 & under free
Medal: Yes
Shirt / swag: Yes

Race details →Register on official site →

Cupid's Chase 5K — Pittsburgh

Sat, Feb 13, 2027 · 10:00 AM (check-in 8:00 AM)

Pittsburgh (PNC Park, 115 Federal St), PA

Price rises Nov 30

5K

The wacky bitStart your Valentine's weekend at PNC Park — white shirt if you're single, red if you're taken.

Price: $40 early bird (price increases after Nov 30, 2026)
Medal: Yes
Shirt / swag: Yes

Race details →Register on official site →

Cupid's Undie Run — Pittsburgh

Sat, Feb 27, 2027 · 2:00 PM (party 12:00–4:00 PM)

Pittsburgh (McFadden's, 211 North Shore Drive), PA

~1 mile ("mile-ish")

The wacky bitPittsburgh strips down for charity — a short undie run from McFadden's on the North Shore, party before and after.

Price: $40.00
Medal: Not listed
Shirt / swag: Not listed

Race details →Register on official site →

No races match that search — try a city, a race name, or 'santa'.

Frequently asked questions

How many pittsburgh are listed?

5 upcoming pittsburgh are listed on this page.

What is the next one?

2026 Jingle Bell Run — Pittsburgh on Sat, Dec 5, 2026 in Pittsburgh, PA.

Where are they?

Pennsylvania — in Pittsburgh.