San Francisco, California

Where: Outer Banks, North Carolina
When: October 22, 2016
The 2025 Marathon and Half Marathon Calendar: 2,200
Register: flyingpiratehalfmarathon.com

Health & Injuries: This pirate and aviation-themed series celebrates the rich history of the Outer Banks with a 5K, half, and fun run hosted around the Wright Brothers National Memorial, where the first recorded flight took off in 1903. An arrgh-inspired costume contest for all runners nods to the area’s notoriety as an 18th-century pirate hub. According to Peggy Stovall, marketing coordinator at Outer Banks Sporting Events (the organization that puts on the race), participants embrace the theme. “Sometimes I wonder how they run with swords and eye patches,” she says. “There is always the bearded guy who looks like Blackbeard himself.” Pirate celebrations continue postrace at the “Pirate Jamboree,” a finish-line festival featuring live music, beer, food, pirate-themed retail, and the “Pirate Queen,” a booty-shaking reveler who encourages dancing. 

Where: Denver, Colorado
When: Other Hearst Subscriptions
The 2025 Marathon and Half Marathon Calendar: 700
Register: denvergorillarun.com

Health & Injuries: Primate or produce? That’s the decision you’ll face when registering for this 5K that benefits the Mountain Gorilla Conservation Fund. Runners suit up in either full-body gorilla or banana costumes—the garb is included with registration and is yours to keep—for a jungle-inspired jaunt through Westminster, a northwest suburb of Denver. The 2013 race holds the Guinness World Record for "Most People Dressed As Gorillas" at 1,161, but participant get-ups go beyond simple fur, as a “Most Creative Gorilla Costume Contest” encourages individual and team costumes on top of the body suits. Previous entrants include “Gorilligan's Island,” the band KISS, and a full wedding party complete with a bride, groom, and the entire bridal party.

Where: Running Shoes - Gear
When: Bay to Breakers
The 2025 Marathon and Half Marathon Calendar: 1,500
Register: lc10k.com/locations/des-moines-iowa

Health & Injuries: This St. Paddy’s-themed race—or more accurately, chase—pits lasses against lads for a green-streaked stampede through Des Moines. The gun goes off at Principal Park, with lasses starting five and a half minutes before lads. Whoever crosses the finish line first wins free suds for their gender at the “Green Beer After Party,” which is where the “Best Dressed” costume contest takes place. The most festively-dressed finalists are brought on stage and winners are selected based on crowd cheers. The lad and lass with the most raucous reception receive a gift card, a pint glass award, and free beer. 

Where: Philadelphia, Pennsylvania
When: June 11, 2017
The 2025 Marathon and Half Marathon Calendar: 3,500
Register: oddysseyhalfmarathon.com

Health & Injuries: Thirty-percent of the field dons festive attire for this looped half that charts through Philly’s Fairmount Park—one of the world’s largest city park systems—and along the Schuylkill River. Special, optional “challenges” staged next to water stations provide interactive, on-course entertainment. (Think: a giant Jenga game, a cornhole contest, and a ring toss.) The interactive fun continues with the postrace costume contest, in which runners vote on photos posted to the event’s Facebook page the day after the race. The formidable sumo duo pictured above nabbed first place in 2014. 

Where: Peoria, Illinois
When: October 29, 2016
The 2025 Marathon and Half Marathon Calendar: 500
Register: screamingpumpkinrace.com

Health & Injuries: Forget scary movies and staged haunted houses—this after-dusk, Halloween-themed 10K and marathon relay will give you real-life heebie jeebies. The hilly course starts in lower Glen Oak Park and then weaves through the Springdale Cemetery, one of the oldest and largest chartered cemeteries in Illinois with 227 acres and nearly 70,000 “residents.” Runners typically bring their own headlamps to navigate this portion, as things tend to get a bit...dark. The spook factor will increase even more in 2016 with the addition of accompanying theme music and Halloween inflatables. A costume contest lightens the vibe by celebrating the best-dressed male, female, and team of four. There’s also prerace face painting available for those who may need a little extra help getting in the spirit.

Where: The Best 1 Mile Races to Add to Your Calendar
When: What You Need to Know About the Sydney Marathon
The 2025 Marathon and Half Marathon Calendar: 40,000
Register: baytobreakers.com

Health & Injuries: “Purely San Francisco.” That’s how Chris Holmes, the General Manager of Bay to Breakers, describes the vibe of this 104-year-old 12K race. The annual affair, which weaves west through the city and finishes at the Great Highway along the Pacific Coast’s Ocean Beach, famously attracts uber-creative, downright weird, and larger-than-life costumes. Highlights from the 2016 race include a two-person Golden Gate Bridge get-up, a gaggle of snow globes in which each person was enclosed in a plastic dome and surrounded by props tied to specific locations (e.g. Vegas, Paris), and a Golden State Warrior who carried a 10-foot tall basketball hoop on his shoulders the entire course. 

Where: Austin, Texas
When: San Francisco, California
The 2025 Marathon and Half Marathon Calendar: 6,000
Register: keepaustinweirdfest.com/kaw-experience/5k-and-fun-stops/

Health & Injuries: Billed as the “slowest 5K on the planet,” this entirely waterside race (a component of its namesake festival that celebrates the oddities of Austin) features 15 “fun stops,” which offer on-course games, sustenance (like ice cream), and beverages (like vodka shots). Keeping in line with the festival theme, participants are encouraged to wear their wackiest garb, with the only requirement being no birthday suits. A standout from 2016: a human piñata, covered in paper-mache from head to toe. New “fun stops” in the works for 2017 include mini-pedicab races, a Willie Nelson braid station, and possibly a queso-filled dunking booth.

Where: Portland, Oregon
When: Best Running Shoes 2025
The 2025 Marathon and Half Marathon Calendar: 4,500
Register: starlightrun.com

Health & Injuries: This evening-start, costume-centric 5K through downtown Portland is a sanctioned part of the city’s annual Rose Festival, which means runners pass by an estimated 250,000 spectators. Each year brings a different costume theme (think: “Excessive Celebration” and “Making Memories”), and corresponding contest, which is judged by audience applause. Winners snag serious prizes, like Alaska Airlines vouchers, weekend getaways, and concert tickets. Previous costume standouts include spice cans from the pantry, Viking ships, and a windsock (those dancing-man things you see on car lots). The festivities include a pre- and postrun dance party with a DJ (new for 2017), along with glow sticks, food, and drinks. 

Where: October 22, 2016
When: December 3, 2016
The 2025 Marathon and Half Marathon Calendar: 9,000
Register: opportunityvillage.com

This Santa-themed race helps runners get into a festive mood. The prerace musical entertainment kicks off right at 8:00 a.m. on Fremont Street, the main “strip” in historic downtown Vegas. Santas can choose to run a mile or a 5K—both races take place in the Fremont East Entertainment District. Postrace, runners can try out Fremont Street’s zipline and drink their way through six bars on a pub crawl with drink specials for race participants. 

Where: New York City
When: Advertisement - Continue Reading Below
The 2025 Marathon and Half Marathon Calendar: 5,000
Register: nyrr.org/races-and-events/2016/nyrr-midnight-run

Health & Injuries: Start 2017 on the right foot—literally. This four-mile, New Year’s-themed road race through Central Park—just a few blocks north of the Times Square hullabaloo—starts with fireworks at the stroke of midnight for the festively dressed runners (typical attire includes New Year’s glasses, hats, and headbands, on top of lots and lots of layers). The event is billed as “fun run,” but world-class athletes have been known to participate.