Going East on Bloor Street by subway, bus or car, you cross the Prince Edward Viaduct made famous by the Michael Ondaatje book In the Skin of a Lion. This bridge was, until recently, also infamous for having a high suicide rate. The city installed barriers to prevent people from jumping off the bridge into the Don Valley below. After you cross the Don Valley the street name changes to Danforth and there are lots of Greek restaurants. The main section of restaurants and cool shops is between Ellerbeck and Pape with Carrot Common at Chester subway being ground zero.
The best way to get there from downtown is to take the Bloor Danforth subway - get on the very front of the subway and look out the front window for a cool view of crossing the bridge. Kids love it.
Alternatively, there is the bike path along Bloor which ends at Broadview/Danforth. This route allows you to stop in the middle of the Prince Edward Viaduct for a spectacular view of the Don Valley south to the lake including all the skyscrapers of downtown. Or another bike route is to travel along the Don bike path from north or south and exit the path at Pottery Road long uphill warning with the reward of Dairy Queen at the top of the hill. This DQ has one of the best views of the city. From the DQ head south on Broadview to the Danforth and then to the east.
By car - assuming you are coming from another city - take the 401 to the DVP, head south on the DVP to the Bloor exit. Exit and follow the road up the hill and you will come to a light - turn left. You are at CastleFrank subway and about to cross the bridge which will become the Danforth once you pass Broadview.