Founded in 2007, Jane's Walk, the annual celebration of urban theorist and advocate Jane Jacobs, has grown into an international event that takes place in 68 cities across the world and involves over 400 guided walking tours. As the city where it all started, Toronto thankfully leads the way with over a 100 walks scheduled for the weekend of May 7 and 8th. Needless to say, there's a lot to choose from. With that in mind, I've put together some of my top picks for the weekend. As much as they reflect my interests, these picks also highlight some of the better tour guides out there and attempt to offer a diverse selection of what the event has to offer those interested in learning more about Toronto.

Historic Yonge Street: A Work in Progress / Saturday, May 7, 2011 / 11:30am
Lead by Ken Greenberg and Marianne McKenna of KPMB Architects along with Denisa Gavan-Koop of Councillor Kristyn Wong-Tam's office, this walk will explore the area of Yonge currently being studied as part of the Yonge Street Planning Framework, which aims to find strategies to preserve the area's unique historical character.

The 5th Annual Retracing Stop Spadina Jane's Walk / Saturday, May 7, 2011 / 11:45am
To some degree, this is the quintessential Jane's Walk in that it relives one of Jacobs great battles (and subsequent victories) and encapsulates much of what she stood for. HiMY SYeD leads a three hour tour that traces the path of what would have been the Spadina Expressway, had community activists not manged to successfully halt its development. Even though the expressway was never fully realized, one can still spot plenty of evidence of the former preparations for its arrival.

Graffiti in Toronto / Sunday, May 8, 2011 / 1pm
Guided by Jason Kucherawy, this tour serves as a good basic primer on Toronto graffiti, a subject that's become quite controversial since Rob Ford was elected mayor of Toronto. A good way to see what all the fuss is about, there's will also be plenty of discussion along the way. A must attend for those blogTO commenters who can't get enough of the vandalism vs. art discussion.

A Hipster's Guide to Ossington / Sunday, May 8, 2011 / 2pm
Time to dial up the irony by studying "the hipster in its natural habitat: at independent cafes, vintage clothing stores, art galleries and "Pho-dives." Find out how it is that this creature effects such change in urban areas across North America.

Dirt: The good, the bad and the sexy in Riverside / Sunday, May 8, 2011 / 10am
Co-led by the Executive Director of Jane's Walk, Jane Farrow, this tour of Riverside will discuss "how neighbourhoods can be considered grimy and undesirable at one moment and a chic and slick place to live and work the next." Local Councillor Paula Fletcher will also be on hand "to offer insights into the development and planning of the neighbourhood."

Parkdale, Scummy Parkdale / Sunday, May 8, 2011 / 2pm
Lead by author and Toronto-expert Amy Lavender Harris, this tour takes participants through one of Toronto diverse neighbourhoods and will explore "how historians, city planners and writers have imagined Parkdale's darkest corners, the effects of gentrification and the prospect of finding asylum in one of Toronto's most multifaceted districts."

Nathan Phillips Square: Our concrete manifestation of Peace, Order and Good Government / Saturday, May 7, 2011 / 3pm
Take a walk with the city's best known psychogeographer, Shawn Micallef. Always an insightful guide, the concrete-loving author of Stroll will explore what is arguably Toronto's most important public space. Bonus: this tour will intersect with John Lorinc's "Arthur Goss, Charles Hastings and the Fate of Elizabeth Street. Two for one!

Iconic Gay Sites / Sunday, May 8, 2011 / 3:30pm
Most everyone knows that Church and Wellesley is the heart of Toronto's gay community, but the fascinating history of the surrounding neighbourhood doesn't get as much attention as it should. Visit the site of the former Charles Tavern, where proto-Pride parades started as part of Halloween celebrations and find out how the concrete high rises in the area gave birth to the Village. Led by Tim McCaskell.

Discover the Toronto Islands / Sunday, May 8, 2011 / 12:30pm
When was the last time you got out to the Island? It's been a while for me...so this is the perfect excuse to hop on the ferry and check out Toronto's old cottage country. No word yet on whether or not a trip to the nude beach at Hanlan's Point is on the docket. Led by Steve Fry, President of Friends of Toronto Islands.

Cabbagetown Arts Walk / Sunday, May 8, 2011 / 10:45am
Join Mayor Rob Ford's Special Advisor on Arts & Culture, Jeff Melanson, as he tours Cabbagetown, one of Toronto's most historically rich neighbourhoods. On the way you can badger hime about arts funding and ask him what he thinks of Toronto's graffiti scene.

Other Jane's Walks on our Radar:

• Brunswick Ave. - It's Literary and Built Form (Guided by Mark Jull)
• Annex: Jane Jacobs Audio Tour
• Art & the City Tour (Guided by Walk T.O.)
• Pedestrian Infrastructure: U of T Edition (Guided by Dylan Reid)
• Regent Park Revitalized (multiple tours)

There s also a Jane's Walk app (iPhone only) that can help you choose which tours sound like they're up your alley.

Lead photo by Portraits of Toronto in the blogTO Flickr pool.