Chicago’s Hyde Park is perfectly situated and laid out for a day-long “book crawl.” For the avid bibliophile, this college community that surrounds the University of Chicago as well as several smaller institutions such as the McCormick Seminary, is always humming with the latest in intellectual culture. Just walking around down there always makes me feel smarter!

Starting at the Seminary Co-Op is always the best as it’s massive selection thousands unique titles crammed into the tiny basement of an academic building on South University Avenue will wear even the brightest mind out after a couple of hours of browsing. Bring your watch though, the small twisting stacks of books have very few duplicate copies and it’s easy to loose yourself for hours upon end in the space of 3 feet of shelving. The Seminary Co-Op is truly a cooperative, and is owned by it’s customers. For a nominal fee you too can join in and get your very own share of the profits and discounts on books.

From the Co-Op wander up the street to 57th street and then down a couple of blocks until you get to 57th St. Books which is part of the same cooperative as the Seminary Co-Op. Where the Co-Op is mostly academic and no-fiction books however, 57th street is a wonder of 5 rooms (again in a basement) of popular culture books, including a large and extensive children’s area. Your Co-Op membership gets you privileges here as well.

After an exhausting beginning at the cooperative stores, stop in to Edwardo’s All-natural pizza for a great piece of organic, all natural pizza – Chicago Style. This place has the traditional deep-dish and stuffed Chicago Style pizza, but with a ‘healthy twist.’ If any pizza weighing over 5 lbs and consisting mostly of cheese could be considered healthy. It’s worth every calorie, however, so go ahead and get the stuffed.

Renewed and rejuvenated by Edwards, finish your day off with stops at the two great used bookstores on 57th St, O’Gerra & Wilson, LTD. and Powell’s Chicago. O’Gerra & Wilson is one of the oldest booksellers in Chicago and a great place to find rare or first editions of books if you’re an avid collector. Powell’s Chicago, which inspired the famous Powell’s Bookstore in Seattle, deals mostly in remainder books and therefore is a great place to find unique and hard-to-find editions of books you though only existed in libraries.

After a full day of intellectual activity on your Book Crawl, you might just be ready to follow it up with a bar crawl. Or perhaps a cupcake crawl?

Chicago is famous for the Sears Tower and the 20+ miles of paths on Lakeshore Drive. When the sun is shining, you’ll find hundreds of people running, biking, skating and generally exercising on Lakeshore Path. In inclement weather, you’ll find the hearty and brave climbing to the top of the Sears Tower to raise money for charity. With all this exercise going around, it’s good to know where in the city you can get the perfect cupcake.

Cupcakes in Chicago, and a growing number of other cities around the country, are no longer the purview of children’s parties and Mickey mouse icing. In Chicago, cupcakes are serious business. Like going out for drinks or coffee, going out for cupcakes has become the thing to do among the socialites of Chicago society. Hands down, the leader of this revolution, and perhaps the cause of i,) is a cupcake bakery on North side of the city by the name of Cupcakes. Here you can get just about any flavor and icing combination, depending on which week you stop by (their menu changes). If you’re set on a favorite, however, don’t be late because they frequently run out before closing time.

Cupcake bakeries abound in Chicago, and if you’re very hearty you might consider taking on a Cupcake Crawl. Yes, you heard me right. Large groups of people often get together to ‘crawl’ around the city on public transit sampling cupcakes from around town. This practice, while it’s been happening for a while, was made famous by Chicago Bites a foodie blog based in the windy city. Their crawl sold out and took the city by storm, making local and international press. Don’t worry if you missed it though, you can print out their itinerary and directions and take yourself on your own personal tour with your closest sugar-loving friends.

After a day of eating every cupcake in site, you might just need that run down Lakershore drive. Or perhaps the full Chicago Marathon!