Boston Urban Dare: 2008

Date: April 25, 2008
Racers: Matt "Squashy" Haldeman and Jesse "Fatman" Morrow
Event: "One Day Amazing Race"
Distance: about 6.2 miles running plus 7 stops on the Greenline



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Map of our route.

Matt and I wondered around the Common up by Joy Street. We looked at the large relief that depicted the founding of Boston and Puritans giving Indians things in trade. Yet, nowhere could we the plaque commemorating the Oneida Football Club that had founded American Football. What was more stressful was that the tour guide who dressed like Ben Franklin had sent us here to find it.

“I don’t think Ben knows what he’s talking about.”

“Maybe he wasn’t early to bed and early to rise. Wisdom just went out the window!”

Frustrated by our inability to find the first clue in the race, the team of Squash and the Fatman returned to the Information Center on Tremont. There a team of two women in the pale blue Urban Dare shirts was asking about the plaque. The guy behind the counter was being very helpful, showing the women on the map of the Common exactly where the plaque was. The two women then ran to the door.

Matt quickly grabbed the guy’s attention: “Yeah, we’re looking for the same thing.”

The guy merely responded, “Follow those girls!”

Urban Dare Tanka:
Out the door adieu
Squashy and the Fatman flew
After other two
Dressed the same in pale blue
To a place which no one knew

We followed the two women into the brightness of the April sun. They zigged and zagged about the Common in what appeared to be an attempt to lose us (it was a race after all). I pointed to the ball fields, “I think it would be over there.”

Matt did no such guessing “But they’re going that way!” So we followed the women toward Beacon Street.

Near the end of Spruce at the Common, stood a tall five and a half foot plaque. It didn’t seem like anything that one would find in the fresh creative destructive America. Instead it appeared as some Victorian gothic monument. I pictured us walking from Thrushcross Grange to see Heathcliff in all his morose splendor.

After some careful negotiations, one of the women on the other team took our picture in front of the monument; then Matt took theirs. We exchanged digital cameras and Matt and I were off to the next clue.

The Urban Dare is described as a “one day Amazing Race.” It’s one part photo scavenger hunt, one part city orienteering. Each team of two is given a set of 12 clues and each clue is a place in the city where the team is to go. The clues can either be a photo spot – like the Oneida Football Club plaque – or the spot of a “dare” (some sort of mental or physical activity).

At 11:00 AM the starting line was filled with over 150 people, over seventy teams, in the pale blue Urban Dare shirts milling about. There is a wide range of teams. Some, such as Squashy and the Fatman, were seeking to win the great race. There was some seeking an enjoyable day traveling the city. One team was preparing themselves by sharing a Camelback filled with Cape Codder.

One of the less competitive teams asked us, "So you're going to try to win?"

"Well, it is a race isn't it?" – This was Matt’s and my second Urban Dare together and this year we were planning to improve upon our 11^th place finish from aught-7.

Before moving to the actual race, the teams have to answer a trivia question involving the city of Boston. Per example: "On January 15, 1919, there was a flood of what substance in Boston's North End?" We were given multiple choice answers and I immediately made my way, taking Matt with me, to the spot on the field for molasses.

For those that don't know, in 1919, the Purity Distilling Company was located on Commercial Street overlooking Charlestown. A large tank containing Purity's molasses, 50 feet tall and 90 feet in diameter, collapsed. It released 2.3 million gallons of molasses into the streets. The flood of hot sugar rushed down the streets at an estimated speed of 35 mph. The waves flattened the local firehouse as the molasses destroyed the first floor causing the upper floors to collapse. The molasses killed 21 people and injured over 150 other. For decades afterwards people claimed that part of the North End still smelled of molasses.

My knowledge of the dismal history of capitalism without safety regulations and its byproduct – the Great Boston Molasses Flood – allowed Squashy and the Fatman to get off to a quick start. Once the teams leave the trivia area, you are handed your twelve clues. It is here where knowledge of the game comes into play. You are allowed to use your cell phones and call a friend who would be able to look up the clues and tell you where to find their answers. The best way to do so is to call a friend, who you've notified in advance to be ready, have them go through all the clues and give you locations to the answers. Once all of that's done you get together and plan your route.

We did not actually plan our route as a team. Instead Matt completely deferred to my near encyclopedic knowledge of the Boston streets. As the starting point was the Common and it is centrally located in the city, I planned a route that would take us in a westward path through the Back Bay and the Fenway; then we would hop on the Green Line and go into the city proper for the clues that were on the Shawmut Peninsula.

Once our route was planned, Matt and I set out to try to win. While we were quickly thwarted in the stop (see Oneida above), we were able to make it to the statue of Tadeusz Kościuszko in the Public Garden. Kościuszko was a general and hero in both the American Revolution and the Polish Kościuszko Uprising of 1784 (guess who was the general in charge). This was the site of our first "dare", twenty push-ups each. While my drill sergeant would have been ashamed at the quality of push-ups, they were completed.

We then ran through the Back Bay and the Fens getting pictures taken in front of various places. At the J.P. Licks on Newbury Street we had our second dare. We had to eat a medium cup of ice cream as quickly as possible. We were given a choice of three flavors, of which each team member was required to eat one medium bowl. The choices were black raspberry, chocolate or cow tracks. I quickly rejected Cow Tracks; I figured the chocolate chunks and the bits of peanut butter cup would have made eating it quickly a challenge at best. I chose chocolate in the end, while Matt went with black raspberry, which was slightly easier to eat fast.

The next photo stop was a stumbling block - The sculpture to Tent City. I had never even heard of such a thing. All we knew was that it was on Westland Ave. Several teams were wondering about the Fens where the Fenway meets Westland. This is one of the great things about the race. Most teams do not take it too seriously. Like at the Oneida statue teams teamed up into larger teams in a Nash Equilibrium – working in the interests of all for one own interest – at least in small bursts. Squashy and the Fatman eventually found the Tent City monument with two other teams and we all took each others’ pictures.

The next dare was in front of the John Endicott Statue by the MFA. Here we discovered Matt is not that great of a Connect Four player. The woman who was running the dare was quickly able to defeat him as Matt didn't block her with three blacks in a row on the bottom level. I, thus, had to play a member of the team who arrived while Matt was playing. I was able to defeat him using those skills finely honed in fifth grade Challenge Class. Off we went to catch the trolley to get back downtown.

We met another team on the train. They had done pretty much the same stuff we had done, missing the Oneida stella, however. Later one of them told me that for sure it seemed we would lose as I was about to puke after having to sprint for the trolley that was pulling into Northeastern. We disembarked the train at Government Center and dashed over City Hall Plaza toward the next dare. One again my encyclopedic knowledge of Boston came in handy. I directed Squashy and the Fatman threw the back alleys around the Green Dragon and Bell-In-Hand, while the two we met on the trolley had to fight through the vegetable and fish bazzar – Haymarket. One of the other two was later to tell me he thought about picking up a whole cod and using as a machete to beat back the jungle of people picking out squash and brocolli.

The next dare was the "spellbound" dare. In the Rose Kennedy Rose Garden in Columbus Park, each team was given a word. They then had to search through the garden to find the tags with each of the letters. These tags each had a number from 1 to 26. You were to write down the numbers for each letter and add them up. When you found the correct sum, your passport was stamped and off you went to find the harbor seals in front of the Aquarium.

In an email later received from the organizers we were informed the best story of the day happened at the spellbound dare. Shawn Madden and Alicia Mutrie were given their word, "proposal." Shawn and Alicia diligently found each of the letters and added up the numbers. When they turned in the answer, the organizers asked if they had a bonus questions. Where upon, Shawn got down on one knee and popped the question. As the email says: "That ended their race for the day, but I bet they will remember it for years to come."

Two quick picture stops, at the Aquarium and the Old State House were all we had to do before the final stop. The last stop was the Sweetwater Café in "The Alley" off Boylston. The last challenge was to put together a 100-piece puzzle; ours was a kid's picture of Noah's Ark. While a 100-piece jigsaw puzzle may not sound hard, you try to do one immediately after running for two hours.

Upon completion we asked what place we came in.

"First, do you see any other teams here?"

During a post-game press conference with the Boston Neighborhood Network, Matt was informed of what we won for first prize – $300 and a plaque. We had never even considered that first prize would be that cool. Matt then yelled into the bar to me that we’d won such cash. On the BNN video, from the shadows of the bar, my voice can be heard in surprised celebration.

Next year Squashy and the Fatman will be back as defending champs! Yet, the women with the Cape Codder and others of similar ilk had just as much fun. While none of us can top Shawn and Alicia, the Urban Dare is a great event. If it comes to your town, it's a great way to spend an afternoon with a friend. Who knows maybe you'll get one of these cool plaques too.