A Yankee In Wrigleyville

Sarah Spain: When the 2011 MLB schedule came out months ago, baseball fans everywhere circled the third weekend of June: Cubs vs. Yankees at Wrigley Field. Two of baseball's oldest franchises facing off at the one of the most storied venues in all of sports.

When fellow espnW writer and diehard Yankees fan Amanda Rykoff booked her ticket from LGA to ORD in March, I offered to treat her to the ultimate Wrigleyville experience. As a Chicago native and a lifelong Cubs fan, for me, Wrigley Field, win or lose, is the happiest place on Earth.

We met up a few hours before Saturday's game and I couldn't wait to see her first reaction to the one-of-a-kind neighborhood that is Wrigleyville. And the best part about introducing someone to a place you love getting to see it for the first time all over again, through their eyes.


Amanda Rykoff: To say I was looking forward to the Yankees and Cubs at Wrigley is a bit of an understatement. When two teams that predate the sinking of the Titanic get together for a rare interleague match-up at a legendary ballpark, it's a must-see series. Beyond baseball, I was also looking forward to enjoying the sights and sounds of the area surrounding the ballpark with my tour guide, Cubs fan and Chicago denizen, Sarah.

I knew that the area surrounding the ballpark was called "Wrigleyville," but I honestly didn't realize the extent to which the world revolves around the Cubs on the North Side of Chicago. I've traveled to many ballparks and while Wrigley Field stands apart for many obvious reasons, including its history, what really sets it apart is its residential setting in a neighborhood so devoted to its beloved team, win or lose.

On Saturday, the Goose Island brewpub located across the street from the ballpark had a giant "W" flag up behind the bar to commemorate the Cubs' 3-1 win over the Yankees on Friday afternoon. Walking through the neighborhood, I realized that nearly every bar, restaurant and business had raised similar "W" flags. A Cubs win isn't just a reason for Cubs fans to celebrate; the local businesses join in. This is a neighborhood that bleeds Cubbie blue.


Our first stop was one of the spots proudly flying its "W" flag, The Cubby Bear. The massive three-level bar has been the go-to spot for Cubs fans since it opened in 1953. It may not be the most unique space, or boast the most impressive beer list, but a trip to a Cubs game at home isn't complete without a trip to The Cubby Bear.


The Cubby Bear stood out because of its proximity to Wrigley Field, directly across Clark Street from the mecca of baseball. The famous Wrigley Field marquee can be easily seen through the bar's front doors. Not surprisingly, fans of both teams packed the place. Cubs fans proudly sported Cubbie blue, and Yankee fans rocked the pinstripes and interlocking "NY" logo, making the scene look like a baseball-themed frat party for pledges of Cubbie Phi Beta or Nu Upsilon Upsilon.

The warm and welcoming environment struck me immediately. When I travel in my Yankee gear, I expect to get dirty looks, a few "boos" and even a "Yankees suck" or two. I assumed that Cubs fans, having gone without a title for so long, would resent us Yankee fans coming to town and reminding them of our 27 rings. Instead, everybody was so friendly, welcoming and just plain nice. Instead of "Yankee go home!" I heard "Hey, welcome to Chicago!" Instead of "Yankees suck!" it was "We're so glad to have the Yankees here this weekend." What kind of bizarro baseball world had I entered?


One where a grown man wearing a baseball uniform and one silver Michael Jackson glove can become a local celebrity. I'm talking, of course, about the one, the only, Ronnie Woo Woo. As we walked away from The Cubby Bear down West Addison Street, Amanda and I ran into the Cubs' unofficial mascot, a man who wanders the city of Chicago yelling "Woo!"

For Cubs fans who have run into Woo Woo too many times -- at Spring Training in Mesa, Ariz., at Harry Caray's Tavern at Navy Pier and even on the subway -- the schtick has gotten a little old. "Cubs, Woo! Dusty, Woo! Quade, Woo!" For an out-of-towner who had heard the legend of Woo Woo, but hadn't met the man in all his pinstriped glory, the chance meeting was a perfect addition to our quintessential day in Wrigleyville.

Courtesy of Sarah Spain

Amanda poses for a photo with local Wrigleyville celebrity Ronnie Woo Woo.

After a quick photo op with Woo Woo, I tried to take Amanda to my favorite pre-game spot, Murphy's Bleachers, but one look at the long line out front (another Wrigleyville tradition) and we decided to save that stop for another day. Instead, we headed straight to the Skybox On Sheffield rooftop, arriving just in time to grab some food and beers before the first pitch.

Watching a game from one of the rooftops that rise above the outfield at Wrigley Field is truly an experience unique to Chicago. The buildings that line Sheffield and Waveland Avenues used to be private property whose owners reaped the benefits of their prime location next to the ballpark. In 2002, the Cubs sued the operators of their rooftop bars for copyright infringement; the two sides eventualy reached a profit-sharing agreement.

While nothing can compare to being in the old ballpark itself, there's something to be said for not melting in a little stadium seat on a hot summer day. Rooftops allow fans to move around, pick their own seat and even watch from the air-conditioned interior if the dreaded "swamp butt" strikes. Add an open bar and incredible food -- I had a feeling that a Wrigleyville rookie like Amanda would be blown away by her first rooftop experience.


I had been looking forward to watching a Cubs game from a Wrigley rooftop on Sheffield Avenue almost as much as I had been looking forward to sitting in Wrigley's famed bleachers.

Watching the game from Skybox on Sheffield definitely ranks as one of the highlights of my "Ultimate Wrigleyville" experience. Let's start with the fantastic food (beer-fed pulled pork sandwich anybody?) and even more impressive beer selection (five different Goose Island beers on tap, including Skybox White and Cubby Blueberry, beers exclusive to the Wrigley rooftop and the Wrigleyville brewpub). From the minute we walked in, I was like a little kid in a candy store. Well, a baseball and beer-themed candy store at least.

Of course we were there to watch a game, and the viewing experience did not disappoint. We walked up to the third floor (Skybox on Sheffield has three floors which offer different viewing perspectives and food options), and emerged to see Wrigley Field across the street in all its glory. Sarah and I found two stadium-style seats on the roof located directly behind right field inside the foul pole and settled in for the game.

The views of the field impressed me. Because Wrigley Field is so small, being on the rooftop doesn't feel that much farther than being in the outfield nosebleed seats at bigger ballparks like Yankee Stadium. We had clear sightlines of the entire ballpark and a perfect view of Robinson Cano's RBI double just inside the first base line. Compared with my obstructed view at Wrigley for Friday's game, this was a significant upgrade. I'm a traditionalist who enjoys watching baseball in the ballpark, but the rooftop viewing experience is one that cannot be missed.


We waddled out of Skybox on Sheffield, stuffed to the brim after downing cheddar burgers, pulled pork sandwiches, veggie paninis, root beer floats and plenty of Goose Island beer. The good news was, we didn't have to go far for our next stop. A photographer friend of mine lives in the rooftop building just next door and his front stoop is a great place to people-watch after the game.

Amanda met a few more uber-friendly Cubs fans, we rehashed the plays that cost the Cubs a win, and then it was off to Clark Street for a slice of Ian's pizza. While Chicago is known for its deep dish, one of the best places for a late-night slice or a post-game bite is Ian's Pizza, where the ingredients are far from traditional. They were out of their famed mac and cheese pizza, so we grabbed a slice with BBQ steak and fries on top, and another with chicken, bacon, cheese and ranch sauce (a diet delight!) and headed to our final destination, Sheffield's.

After a long day of sunshine, baseball and brews, it was nice to grab a seat on the big back patio at Sheffield's and reflect on our Ultimate Wrigleyville experience.


Even after three days in Wrigleyville, there's still so much more to see, drink and eat at the ballpark and beyond. You hear that, Ian's Pizza? I am coming back for that mythical mac and cheese pizza. This might need to be an annual trip.


Maybe for the World Series?


There's always next year.

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