What cool places can I go to to eat my lunch in Toronto?

Toronto Island isn't quite free (you need to pay for the ferry), but it's a great place to hang out. On my days off I really like eating in Queens Park, there's plenty of office people doing the same on a sunny day. Toronto's a city of parks - there are tons of little neighbourhood parks that are severely underused on a weekday. One of my favorites is a park in Rosedale that is apparently called http://www.torontofunplaces.com/component/k2/item/219-craigleigh-gardens. On weekdays it's largely empty except for the occasional dog walker and the local nannies pushing carriages around and is a great place to read. It's also got a path down into the http://www.toronto.ca/trees/ravines.htm, where it's easy to spend a couple of hours exploring. It's a short walk to the http://ebw.evergreen.ca/ along the well-maintained ravine paths in the area.

Cherry Beach! Lots of places to chill, walk around, even swim (not everyone swims in Lake Ontario but I love it).

Any park will work, but I think Queen's Park and http://www.trinitybellwoods.ca/ are especially great for people-watching. (Grab an iced coffee or lemonade at http://www.facebook.com/tamperedpress and then walk across to the park for your picnic!) You could hit up the Beach also, spread out a blanket, etc. http://dufferinpark.ca/home/wiki/wiki.php has a Thursday farmer's market, and a cheap community dinner night (pizza oven, I think?). http://www.wychwoodbarnscommunity.ca/pagedisplay.aspx?i=251 is neat to roam around, and has some seats. Their farmer's market is too $$ for me, but it's a nice place for sure, and I think they also have some cheap/free community meal events. If you have a car/bike or don't mind a long walk, http://ebw.evergreen.ca/ is a really interesting place. They have guided tours and also free self-tours, and I imagine you could find a nice spot to have a bite. And of course there are the http://www.toronto.ca/parks/island/ if you don't mind paying the ferry fare. If you're looking for a nice long walk, take the ferry to Ward island, then walk along it to Center Island and find someplace to enjoy lunch on the way -- you see a whole different aspect of the Toronto Islands, the more residential, peaceful side. The U of T courtyards are beautiful -- benches, greenspace. I know Hart House at the U of T has a little area in the basement where students can sit and eat their own food (though it's not particularly pretty). You could probably snag a table on Sammy's patio during a quiet time, they're not too strict about having to buy food first (though please be courteous to those that did pay for their food, especially during peak hours). You could also head down to the Distillery District - certainly atmospheric, and I seem to recall that there are benches sprinkled throughout where you can have a sit and a sandwich. Afterwards, you can grab an ice cream cone, window shop the galleries, check out the chocolate making at Soma, maybe even get cheap rush tickets for a play at the Yonge Centre for the Performing Arts http://www.stageplay.ca/.

-Harbourfront has lots of benches n' stuff by the water. -Sugar beach! -That random square behind the eaton center with the maze! -The park in Kensington Market! -As already mentioned, the roof on 401 Richmond is awesome, and as a bonus, you can wander the building and peer into the designer workshops and wander the art galleries and visit the design-y shops. -On hot days, it would probably be great to hang out at public pools -The UofT campus

Seconding Dufferin Grove and Wychwood. Also Sugar Beach at the foot of Jarvis, and Sherbourne Common one block east of Sugar Beach. A nice secluded spot not too many people know about is https://maps.google.ca/maps?q=Serena+Gundy+Park,+Toronto,+ON&hl=en&sll=49.891235,-97.15369&sspn=29.481488,60.117187&oq=Serena+Gundy&t=h&hq=Serena+Gundy+Park,+Toronto,+ON&z=14 in the Don River system. Take the 34 Eglinton Bus to Brentcliffe, walk north to Broadway, turn right. At the end of Broadway, follow the path downhill and it will take you to a secluded open space. One of Toronto's hidden gems. Also, the Evergreen Brickworks.

I enjoyed people watching and an iced coffee in the park behind AGO - google maps looks like it is Grange park? If I recall, that is also by Chinatown which is a fun outing in itself. And Kensington Market is close too.

I did exactly this at Trinity Bellwoods Park a few weeks ago. There's a kind of ridge overlooking a dog park where people had gathered, so there was even a bit of a show as well. I also did a picnic at the Allan Gardens. The homeless population in parts is pretty sizeable, but you can find a quiet corner, and it's worth it for the conservatory, which is free. Also have you considered taking some of the free tours? Google around, the city runs a number of them. I even saw a few Mefi links about them, which I failed to favorite.

The Beach aka The Beaches. Lovely boardwalk to stroll, great people-watching, lots of trees to lounge under and read. There are also shops nearby to get an ice cream or a coffee (your favorite chain is surely represented). I've passed many a pleasant afternoon doing just this.

There are lots of common rooms and cafeteria's on all the University campuses, and they're usually pretty quiet in the summer. I would imagine the College campuses are similar. And they're generally pretty accessible by transit and spread around the city, so visiting a bunch of them might give you an interesting view of Toronto that you wouldn't get by focusing on the downtown places.