Last. Saturday. was. amazing. A highlight of our time in Portland.

To begin from the beginning, Jeff’s long-time buddy Joey was in town to open a Boot Barn in Troutdale (he’s in sales for Wolverine shoes). Last minute, Jeff, Joey, Lindsay, Daniel and I signed up as a team of five for Cartathlon II, a four-hour, city-wide scavenger hunt anchored by food cart challenges. Up for grabs: a year’s worth of free food cart food, free Keen shoes and other awesome prizes.

First, we dubbed our team “Sloppy Jerrys,” inspired by the moniker of the McMenamins Tavern & Pool sloppy joe Jeff ordered at midnight after our recent 80s night excursion. Random, yes. Daniel fashioned a Sloppy Jerrys logo and I ironed it onto matching team shirts. Ready for battle!

After a shotgun start, we and the other costumed teams were off, unaware of the hard work ahead: Our team covered 13+ miles by foot and by public transit. At least half by running. I blew my Nike+ Fuelband daily goal out of the park. It was an insane workout, and I’m guessing the other teams did not run as much as we did or there would’ve been many more beat-down teams at the after-party.

A smartphone app guided us through mandatory challenges and bonus opportunities – six food carts hosted the mandatory challenges, which ranged from chomping a messy Whiffies fried chocolate and peanut butter pie without using our hands, to a blindfolded cheese-tasting contest at the Grilled Cheese Grill (which Joey dominated!), to a gingerly-handled water balloon toss at KOi Fusion. We snapped photos through the app to document our progress while deciphering riddles to rack up bonus points – like finding the bizarre 24-hour Church of Elvis, posing by Smut store’s box of “Instant Relatives” vintage family snapshots, and getting a photo with the smoochy owner of Mississippi Avenue’s light bulb store. Also, my team entrusted me to carry the Willamette Week-stamped egg the organizers handed us at the beginning of the event, which I carefully protected during our wild adventures.

At the final cart, the awesome, waffle-slinging FlavourSpot, we completed the final “everyone take a bite of the waffle while it’s in Daniel’s mouth” challenge and joined the after-party to await the results.

First cart challenge done!

Sloppy Jerrys = fourth place of 72 teams! By the skin of our teeth, we made the cutoff for the final challenge, duking it out with teams “The Dirty Ashleys,” “Who Carted?” and “Carte Asada” on stage for the year of free food cart food. In front of hundreds of lively fellow Cartathlon participants, each of the top four teams divided into three roles: trivia, selecting surprise food boxes, and eating. Lindsay and I took the trivia portion and fielded food cart-related questions. (Thankfully, we had attended last year’s Eat Mobile, which was fodder for a lot of the questions.) For each wrong answer, Joey selected one of approximately 40 takeout boxes holding a surprise food, such as a half-gallon of berries, BBQ beef, cheese curds, pickles or a pile of garlic. Those ingredients built a disgusting waffle sandwich that our volunteer eaters, Jeff and Daniel, had to overcome in a two-minute eating race to victory. We semi-lucked out and got huge bags of icy cold strawberries, marionberries and some yucko pickled pears. (Other teams didn’t have ingredients that meshed as well – like fried onions, crushed waffle cones and big slices of ham. Blegh.)

The air was tense as the teams readied for the final eating challenge. Jeff, Daniel and the other six eaters arranged themselves into the awkward required stances: blindfolded Jeff standing behind a kneeling Daniel and stuffing the monster waffle sandwich into Daniel’s mouth. After the two minutes, the whole team could join in for a one-minute gaggy feeding frenzy. And…

Sloppy Jerrys = second place of 72 teams! While we didn’t score the free food cart food for a year, we did take home VIP tickets to OVO, a touring Cirque du Soleil show coming to town next month. We were high as kites after the win! Sweaty, full of fruit and victorious, we toasted our triumph at Amnesia Brewing, Crow Bar and later at home around the pagoda-covered fire pit.

Best. time. ever. Sloppy Jerrys rule!

Lining up at the Cartathlon starting line

Others were a little more dressed up than us…

Like I said…little more dressed up than us…

Each team got an egg to protect throughout the event

Our team shirt (slightly dirty after a challenge)

Blue Moon McMenamins bar in Northwest

Riding a Trader Joe’s shopping cart

Joey and Daniel with soft hands in the KOi Fusion water balloon toss

Chomping down cheese fries at Big Ass Sandwiches

Big Ass Sandwiches cheese fry challenge done!

Getting our drink on outside Dante’s in downtown

Jeff and I posing at the 24 Hour Church of Elvis

Whiffies pie = done! (Love that place…)

Riding the ponies at Cartopia food cart pod for bonus points

Outside Laurelhurst Theater (and getting pretty tired)

Victory at Oregon Ice Works (and 9,000 bonus points!)

Brain freeze from the Oregon Ice Works one-minute, five-scoop challenge

Finding our “Instant Relatives” at the Smut store

Cheese taste-testing at Grilled Cheese Grill

Surprise smooch from the lady at the Mississippi Ave. light bulb shop

Getting the rundown of the final food cart challenge at FlavourSpot

A waffle spurring an intimate moment between friends 🙂

Finishing off our last food cart challenge

Mugging for our final food cart challenge at FlavourSpot

“Did we make the top four?”

Preparing our mess of a waffle sandwich

Ready to eat!

All that remained after the final eating challenge

Soaking in our win at Crow Bar