I’ve gotten to the point in my pregnancy (three weeks to go!) that I’m doing anything and everything to get my mind off the waiting-for-baby game.  Waiting sucks.  My favorite way to pass the time?  Researching races, of course.  Not that I’ll be racing again anytime soon, but it is fun to build an imaginary race calendar.  Since writing the Obstacle Races: Cool, But Are They Safe? post, I’ve been looking into other ‘unusual’ races with a fun hook.  Here are ten of the wackiest, tackiest, and most insane races that I’ve come across in my Internet browsing.


Streak the Cove 5K – Kissimmee, Florida


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The Streak the Cover 5K is a “clothing optional” 5K held on the Cypress Cove Resort in Kissimmee, Florida.  Runners are encouraged to wear “as little or as much as they want…” although sunscreen is highly recommended.  All I can think is, “No clothes… Does that mean no chafing?!”  And, “Man, my boobies would hurt.”  Anyway, proper nudist etiquette must be followed at all times (put a towel down before sitting and no camera or cell phones allowed on the property).  And yes… runners still get a free T-shirt for entering.


Cross Bay Half Marathon – United Kingdom


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This Half Marathon is a trail race that crosses beautiful scenery, a tidal bay, and two rivers.  The quickest route between the counties of Cumbria to Lancashire, the crossing dates back as far as the 13th century, when monks would guide travelers across the bay on foot.  This is believed to be the only race in the world that crosses a tidal bay – pretty neat!  But expect a few blisters – you are running through several water challenges and wet sand, after all.


The Urban Dare – Cities Throughout America


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The Urban Dare is a race where teams of two solve a set of twelve clues, including trivia, photo hunt games, and mental and physical challenges.  To move onto the next challenge, teams must take photographs or complete dares, which may include climbing a wall, solving or puzzle, or other activities.  Teams can run, walk, or use public transportation – but not cars – to move between checkpoints. The events usually take two to four hours and cover a total of 5 – 7 miles.


The Runyon 5K – Bronx, New York


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I’ve done a race that finished inside a stadium – but the Runyon 5K is unique in that it occurs entirely within the Yankee Stadium.  Runners traverse concourses, ramps, and nearly 268 stairs to travel 3.1 miles through the stadium, finishing up with a victory lap around the warning track (near, but not on, the actual field). To prevent bottlenecking, start times are staggered.


Skirt Chaser 5K – Tempe, Arizona and Denver, Colorado

Denver Skirt Chaser 5k

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The Skirt Chaser 5K mixes “flirting and racing.”  Most participants sign up as a couple, and the women get a 3-minute head start on their partners, who try to ‘catch them’ on the course.  If you’re single and looking for a love who appreciates racing as much as you do, you wear a special sticker – who knows, maybe you’ll meet someone nice on the course!


Crystal City Cave Run – Crystal City, Missouri


This race is definitely in the wackiest location – it’s an underground 5K!  The race goes through the Crystal City sand mine, taking runners past underground lakes, over wet sand, under air shafts, and on top of sand dunes.  It’s a two-loop course and, save for a small portion at the start, takes place entirely underground. 


Night of the Living Dead 5K – Salty Lake City, Utah


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Like the Skirt Chaser, this Halloween-themed race features a slight head start for some participants… but it’s humans v. zombies.  Runners register as ‘humans’ or ‘zombies’ (and zombies are, of course, encouraged to dress up and play the part), and humans get the first whistle.  Two minutes later, the zombies take off.  Race rules specifically state that zombies are not allowed to be aggressive or harass humans.  Eck!  Run for your life!


Napa to Sonoma Wine County Half Marathon – Wine Country, California


I would LOVE to do this race one day.  It’s definitely on my bucket list.  First of all, it’s a scenic half marathon through beautiful wine country, and there’s an awesome wine and music festival following the race.  But more importantly, they serve wine on the course.  Who needs a water stop when you have a wine stop?  Bottoms up!  Oh, and the prizes include over 20 cases of wine in addition to the traditional cash.


The Enduroman Arch to Arc – London to Paris

Whatever. I could totes do that.

Billed as the “world’s ultimate triathlon,” the Enduroman requires participants to run 87 miles from London to Dover, swim the entire English channel, and then cycle 181 miles from Calais to Paris.  Yes.  Seriously.  Alternatively, you can run from London to Dover, kayak the English Channel, and then bike from Calais to Paris.  Your decision.  Only nine people have ever completed the entire race by themselves.  Four relay teams have completed the event.  To qualify to participate in the 300-mile race, you must have completed a six-hour sea swim in 16 degrees or colder water within the last year.  Oh, and the race costs around $8,000 for a single entry.


The Krispy Kreme Challenge – Raleigh, North Carolina and Tallahassee, Florida


Does running 2.5 miles or so, wolfing down a dozen donuts, and running back to the start line sound like your idea of a good time?   Yeah.  Me neither.  But loads of people love to participate in the annual Krispy Kreme Challenge, which raises money for charity.  Part of the challenge is that the running and donut-eating (which, by the way, clocks in around 2,400 calories and 144 grams of fat) must be completed in under an hour.  And yes, there are actually ‘designated puke areas,’ including a puke tent.  Gross!


Would you run nude?  Would you rather be a zombie or a human?  Would you barf if you had to eat 12 donuts in the middle of a 5-mile race?  Would you feel compelled to drink wine at the Napa Half Marathon just to say you did?  I would not run nude ever, I would be a zombie, I would definitely barf after eating a dozen donuts under any circumstances, and I would partake in the booze!



  • Laura May 15, 2012, 2:08 pm

    I’ve actually done one of these races! I’ve completed the Raleigh Krispy Kreme Challenge three years in a row now and love it!!

    • CaitlinHTP May 15, 2012, 2:15 pm

      Have you ever puked? I would definitely puke.

    • Johnna May 15, 2012, 11:14 pm

      When does registration usually open for this race? Does it sell out fast? I would love to do it with my mom next year.

      • Melissa June 1, 2012, 9:44 pm

        I’ve done this one three times too. Love it! I can’t remember when the registration usually opens. It doesn’t sell out too awfully fast. It does sell out but just keep an eye on it and you can get in. They have a FB page and if you like it, you’ll get all the updates. I ate all 12 of the doughnuts last year and kept them all down. Didn’t feel sick in the slightest. I saw a shirt that I just have to have for next year: “I have an iron gut. Puking is for sissies!”

  • Jaclyn May 15, 2012, 2:09 pm

    That cave 5K sounds kind of awesome. I’d love to do that! I did the Virginia Wine Country Half (run by the same people as do the Napa to Sonoma half) and it was an awesome race. In addition to t-shirts and medals, we got engraved wine glasses! And there was wine-tasting at the finish line so your race day supporters could booze it up while they waited for you to come in. Fun times!

    • CaitlinHTP May 15, 2012, 2:10 pm

      That is pretty epic. A wine country race is definitely on my bucket list. Maybe next year??

      • Laura May 16, 2012, 10:54 am

        They also run the Healdsburg half marathon, which I did last year and am doing again this year. Similar course (vineyards, beautiful rollings hills, etc) and wine tasting at the end. That race is still open i believe and is in October.

  • Aundra Weissert @ Fit for Life May 15, 2012, 2:20 pm

    Whoa. This is the best race compilation post I’ve seen!!

    I would definitely love the Urban Dare — there’s one near me this summer. And I would do the Cave one in Missouri.

  • Mary May 15, 2012, 2:23 pm

    The cave race sounds awesome! As do many of the others. And while I’m very unlikely to do the streaking race, if I had to choose between that and the donut race, I’d definitely streak. All that donut eating sounds disgusting! And PS – look at that huge pile of waste from all the empty donut boxes! It’s great that it’s raising money for charity…..but there has to be a better way. Right?

    What a fun post, thanks for sharing!

  • Jonathan | WorldOfDiets May 15, 2012, 2:24 pm

    Night of the Living Dead seems cool. I would definitely do that, but not for the fitness. Just to meet some crazy people.

  • Kendra @ My Full-Thyme Life May 15, 2012, 2:27 pm

    Ummm… my wobbly bits will stay under wraps at all times, thank you very much! 😉 Those are some wacky races! I’m not a runner but I have to say, your blog is intriguing me to take a stab at it. My friend and I have been walking buddies since college and recently she informed me that she has started running. I told her we should sign up for a 5k and she was in! Then… I got pregnant. Maybe next year. 🙂

  • Sunny May 15, 2012, 2:28 pm

    I totally want to do the Napa/Sonoma half. Then again my husband and I honeymooned out there so I look for any excuse to go back. 🙂

    I do not think I could do the Krispy Kreme one, I’d definitely throw up! The cave one sounds very cool and its the closest to me!

  • jen May 15, 2012, 2:29 pm

    i so wanted to do the zombie one, but i chickened out, since ive never done one before. i did though sign up for the color run this summer, where they throw a different color paint on you at each k you run… im so excited they say its the happiest race to run! (and i am training for it, which seems so silly when its only a 5k)

    • CaitlinHTP May 15, 2012, 2:35 pm

      that’s not silly! i’ll be training to run a 5K this summer 🙂

    • Anna S. May 20, 2012, 2:12 pm

      I’m also training for the color run! I feel silly since it seems like more of a fun race, but I figure I still want to complete it!

  • Hillary May 15, 2012, 2:44 pm

    My boyfriend lives in Raleigh, and I always joke with him that he needs to run the Krispy Kreme 5K. Never gonna happen!

  • Samantha May 15, 2012, 2:45 pm

    I would never run nude, I would be a human running away from zombies, I would totally barf eating those donuts, and I think I would pass on the wine! Wine goes straight to my head, I get tipsy too easily.

  • Angela @ Eat Spin Run Repeat May 15, 2012, 2:46 pm

    The Urban Dare sounds like a fun one, as does the wine one!! I’d definitely do a little wine tasting along the course!

  • Laura May 15, 2012, 2:48 pm

    Have you ever heard of the gorilla run in London? Everyone runs in a head to toe gorilla costume! haha http://www.greatgorillarun.org/london

    • Caitlin May 16, 2012, 10:17 am

      That is epic.

  • Lindsey May 15, 2012, 2:49 pm

    My husband was just telling me about the Zombie race the other day! I would love to run through wine country, but I think I would be sick if I drank along the way… I prefer my wine tasting and my running separately 😉
    Maybe I need to do a few more “boring” races before I try these crazy ones!

  • Beth May 15, 2012, 2:54 pm

    There’s a race that runs through the Fort McHenry Tunnel here in Baltimore. The tunnel is long (like 2 miles) so I hear it’s a fun one!

    • Katie May 15, 2012, 3:02 pm

      Oh my gosh, I drive that tunnel often, I could not imagine running through it! All I can ever picture is the scene from the movie “Independance Day”. Sorry, I hope that didn’t just freak you out! 🙂

  • Amber @ Busy, Bold, Blessed May 15, 2012, 3:06 pm

    I heard about a nudist race around here and all I could think was ouch, my boobs!!!! The zombie race would be fun. Whenever my friends ask me why the heck I would ever train for a half marathon, I tell them I’m much more prepared for a zombie apocalypse! Haha.

    I would attempt the KK challenge, those donuts are SO good… not sure how I’d fair with the wine during a race though!

  • Abby May 15, 2012, 3:08 pm

    We have a Krispy Kreme Challenge here in Nashville too!! I’d never heard of such a thing (crazy!!), but my boss and his son do them every year. Last year, the winner ate something like THREE DOZEN Donuts. Yuck. But you get 2 minutes knocked off your time for every donut you eat. So maybe it’s worth it? Still, yuck.

  • Katie @ Peace Love & Oats May 15, 2012, 3:24 pm

    The Crystal Cave one sounds awesome, especially since I live in Missouri!!! I’ll have to check that out!

  • April May 15, 2012, 3:38 pm

    There’s a pretty awesome run that was done for the first time a few weeks ago- the Quarry Crusher Run in Columbia, SC (http://quarrycrusherrun.com). It goes down into an active granite quarry!

    I would do a nude race EXCEPT like you I have big knockers and it would hurt so bad for them to be flopping around while running even 5 FEET much less a 5k!

  • Laura @ She Eats Well May 15, 2012, 3:44 pm

    The zombie one is pretty funny. I love races simply because they make you feel like you’re part of a community of other crazy runners! The Napa to Sonoma is on my list too! And I’ve recently read about the Krispy Kreme race…I would seriously puke.

  • Maggie @ runningonfroyo May 15, 2012, 4:29 pm

    I’ve done the Krispy Kreme Challenge because it’s a pretty big deal at my school (NC State)- except I just signed up as a casual runner (AKA you don’t have to eat all the donuts) but you still get a box of donuts to run back with, and I definitely ate one after I finished. 😀 The Napa Valley half is DEFINITELY on my bucket list now. That sounds awesome!

  • Caitlin @ This Bride's Joyride May 15, 2012, 4:32 pm

    I’ve always wanted to do the krispy kreme run! The underground crystal cave run sounds so neat – I wonder what the air is like down there!

  • Liza May 15, 2012, 4:54 pm

    I could ONLY run nude if I was tipsy from drinking wine while running! 😉 Otherwise I would be soooo self-conscious. Hahaha! No wine = inhibitions = no nude run! I would never do the donut run, I hate barfing too much. Would definitely do the underground one, it’s probably nice and cool down there. And I would be a zombie too, although I would likely sweat all the makeup off in the first mile.

    Fun post Caitlin!

    • Liza May 15, 2012, 4:59 pm

      Oh and I have done the Great Urban Race here in Atlanta (similar to the Urban Dare) and it was a blast!

  • Ashley May 15, 2012, 5:00 pm

    I need to do the Yankee Stadium run when I move back to NYC. Such a cool race!

    The Medoc Marathon in France is similar to the Napa race you wrote about above where you taste different wines throughout the marathon. I’m sure that’s such a fun race to do with friends.

  • Angela May 15, 2012, 5:00 pm

    If you are into Formula 1 they do races at the Silverstone circuit in the UK. Would be a nice easy course as I don’t think there are many hills in motor racing!

  • Kate May 15, 2012, 5:01 pm

    No nude running (the “girls” would hate me), I would be a human (I would probably PR out of fear), I think I could probably manage the doughnuts (I have a steel stomach, and I would definitely enjoy some vino out on the run! I think the cave run would be awesome event to participate in!

  • Rachel May 15, 2012, 5:08 pm

    have you seen or heard about “the color run” or “color me rad” races? you wear all white & race volunteers & onlookers throw colored corn starch at you along the course. i just found out about these & i will most definitely be doing one next year! sounds like so much fun 🙂

  • Megan E May 15, 2012, 5:21 pm

    I want to do Urban Dare NYC *so bad* !!! I am going to have to email them to see if it’s okay if only one partner does eating challenges — I doubt they will be vegan! 😉

  • Heather May 15, 2012, 5:50 pm

    That arch to arc sounds intense! Interesting tidbit, my second cousins are I think the 7th or 8th relay team ever to swim across the english channel. They did it a couple of years ago to raise money for pancreatic cancer, which their uncle died of, and we tracked them via video online. There were three of them (brothers) and they each swam one hour legs until they got to the other side, while the other two sat and shivered in a boat alongside the swimmer. It was intense but cool!

    • Caitlin May 16, 2012, 10:17 am

      Wow that is really fascinating! What a cool legacy.

  • Kate @ life's precious moments May 15, 2012, 6:12 pm

    HA! What a fun set of races! I think the craziest race I have will ever run in the Color Run (this July). Other than that I am all about the traditional run 🙂

  • Justy2003 May 15, 2012, 6:27 pm

    I did the Napa to Sonoma Half Marathon last year and loved it! The weather was great, the course was gorgeous, and all the wine at the end was fab! They served a bit of white wine at mile 11 and I definitely partook in that! I highly recommend it…though it sells out FAST!

  • Sarah May 15, 2012, 7:11 pm

    I participated in the Zombie run this year and it was a lot of fun. Oh, I could never participate in a nude run.

  • Army Amy* May 15, 2012, 7:26 pm

    I saw advertisements for a nudist 5k in my area. For a split second, I considered it. (You only live once, right?)*

  • Ebernst May 15, 2012, 8:04 pm

    I ran the Krispy Kreme challenge with my sister this past year! It was so much! We both were casual runners so I ate one doughnut at the halfway point as my “fuel”, better than gu i say! 🙂 And there was lots of puke at the finish line! But so much fun!

    And the Urban Race is coming to Raleigh in Nov! My friend and I are doing it! 🙂

  • Courtney May 15, 2012, 8:18 pm

    I love looking up wacky races! There is a 5k in New Orleans that runs through a cemetery. And there was a 5k around Valentine’s Day where the couples get a white shirt and the single people get a red shirt — so awkward.

  • Allyson May 15, 2012, 8:34 pm

    I completed the Krispy Kreme Challenge in Raleigh. I ate all 12 donuts in about 6 minutes and did not barf (although I felt like I was going to). It took me 51 minutes total. I don’t know whether to be proud or ashamed, but it was awesome 🙂

  • Alli C May 15, 2012, 8:36 pm

    This was such a fun post!! Loved it! 🙂

  • Chazza May 15, 2012, 8:41 pm

    Never even occurred to me that races can be more than just the bog-standard! That Cross Bay race takes place just a few hours from where I live, so it’s definitely added to my list of races to do once I get my fitness back, thanks Caitlin!

  • Mandy R May 15, 2012, 8:46 pm

    I’ve done the Crystal City Cave Run. It was one of the hardest races I’ve done. When you are inside the cave you are running in ankle deep sand. It was wet in some areas so the sand was packed down. Sometimes you are running up a “sand dune” and you are getting no where fast! It was fun though!

  • Britt @ The Busy Bee Writes May 15, 2012, 9:06 pm

    Loved this post!! My husband and I are actually thinking of doing the Zombie run in Missouri this year!

    Our first 5K as a couple, and now annual 10K is the Groundhog Run in KC. It is the largest underground race in the country. and so much fun! I love the wacky races, because it is what got me and keeps me excited about running! http://www.childrenstlc.org/Events_GroundhogRun.html

  • Erin May 15, 2012, 9:13 pm

    I ran the Napa to Sonoma half marathon in 2009 but I don’t recall wine at the aid stations. Maybe I was too distracted by the scenery 🙂

  • Anne Kendall May 15, 2012, 9:46 pm

    What a great post! It’s so exciting to learn that there are races out there other than just the standard pavement races around a few city blocks. I’m on the lookout for fun, funky races in Virginia! I don’t think I’m ballsy enough to run naked, but I think I would *attempt* the Krispy Kreme and the wine-tasting challenges. Hey, why not? Fun post — thanks, Caitlin!

  • Katie May 15, 2012, 9:58 pm

    The Wine Half sounds amazing!!! I have a 30 by 30 list and this might have to be one of the 30 races I do!

  • Earthy Nicole May 15, 2012, 10:25 pm

    “I would not run nude ever, I would be a zombie, I would definitely barf after eating a dozen donuts under any circumstances, and I would partake in the booze!” –DITTO! The puke tents remind me of Catching Fire… where they drink that stuff to make them vomit so they can eat more! Sick.

  • Amanda K. May 15, 2012, 10:42 pm

    here’s another wacky race worth checking out: http://www.colormerad.com/

    and i agree. i would NEVER run nude. never ever never.

    • Anne P May 16, 2012, 8:03 am

      I just heard about Color Me Rad, too – sounds so fun!

  • Angela May 15, 2012, 10:55 pm

    my mom did the sonoma half and i still give her a hard time for not having wine on the course! she did partake at the finish line though 🙂

  • Brianna May 15, 2012, 11:02 pm

    They do the Skirt Chaser here in Portland, OR too. 🙂

  • Lea May 16, 2012, 12:22 am

    As a Raleigh native I really want to do the Krispy Kreme Challenge one day, except I don’t want to eat all those donuts. Random, but I think the guy in that picture lived in my dorm building my sophomore year.
    I did a similar race in Boone except it involved 4 sticky buns instead of donuts. That race was puke free! Or at least when I finished it was.
    A nude 5k sounds like the most painful thing ever. I also feel like watching hundreds of naked people run is something you can never un-see.

  • Dental Accountant May 16, 2012, 1:04 am

    Man, just thinking about that Krispy Kreme challenge is making me sick! Is that an annual event? I’d suggest the nudist run to my friend who’s fond of running naked, with just a pair of boxers on!

  • Sarah May 16, 2012, 7:57 am

    We wanted to do Napa to Sonoma this year..but it sold out in less than a week! …so plan ahead.

    • Caitlin May 16, 2012, 10:15 am

      good to know!

  • Linda @ Lemons May 16, 2012, 8:00 am

    Those are crazy! I definitely could not handle the Krispy Kreme race, but I would be into the Yankee Stadium race, that sounds really fun. I’ll have to find out about the race that goes through the Ft. McHenry tunnel in Baltimore, I’d like that one.

  • Anne P May 16, 2012, 8:02 am

    What a cool post! I almost did the Krispy Kreme challenge last year since I was in Chapel Hill but decided against it. 😉 I love the sound of the Cross Bay Half Marathon, Urban Dare, and of course the wine country half! The Enduroman Arch to Arc sounds INSANE.

  • Anna May 16, 2012, 9:16 am

    Those look like such fun races! It would take a lot of guts for me to race in the hude, I would rather be a zombie, and I would NOT want to eat donuts while running.

    The triathlon club did a “donut dash” as a fundraiser and it was one 5k I was so happy to just be a volunteer for. Thankfully no one got sick but one guy finished like 20 donuts!

    The funnest race I’ve ever done is a Colorblast 5k!

  • Carlee May 16, 2012, 9:17 am

    Some of these look like so much fun! Thanks for sharing.

    I would never do the nude one either, but it reminds me of at my college, UVM, every year on the last day of classes (both semesters) they had a naked bikeride. Yes, this means they were riding naked in Vermont, in December!

    Can’t say I ever did that either :O)

  • Sarah May 16, 2012, 10:21 am

    The wine race reminds me of RAGBRAI – the Register’s Annual Great Bike Ride Across Iowa. It’s a week long bike ride from the west “coast” (Missouri River) to the east “coast” (Mississippi River) in Iowa. There’s tons of beer and parties EVERYWHERE. The party is integral to the ride. I don’t know about wine, but on the one day I did a few years ago I came up this epic climb out of a river valley and at the top I crumpled on the side of the road and then someone handed me a beer. My heat/exhaustion headache was gone immediately!!! Haha, just don’t overdo it or you’ll have a different sort of headache later on.

  • Cecily May 16, 2012, 3:27 pm

    Speaking of donuts, here’s a bike race for ya.. The Tour de Donut is a race in my hometown- for each donut you eat on the 32-mile bike ride over rolling terrian, you get a 5 minute deduction off your final time! Although I’ve never done it, I’ve heard it’s a pretty “sweet” race. 😉

  • Lauren May 17, 2012, 4:56 pm

    I’m doing Napa to Sonoma this year (as a fundraiser for the Crohn’s and Colitis Foundation)! Couldn’t be more excited!

  • Jessica May 17, 2012, 9:10 pm

    Woo, the Krispy Kreme Challenge started at my college (NC State) while I was in school there. I tried it once…I couldn’t choke down the last 1/2 doughnut, puked a lot, and finished 15 minutes over time. Oh well. I didn’t know they did one in Florida now!

  • Claude December 16, 2012, 4:30 pm

    I did this race last year where it was an all guy race {sorry ladies} running bare-chested. It was gross but funny and exhilarating.

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