Well, here's my input. I have ridden to Lowes and Crew Stadium dozens of times day and night all time of the year. Lock to a tree or signpost/lampost.
I would take 4th St north to 17th Ave and east on 17th to Velma Ave and north on Velma to Crew Stadium. This route is the most efficient, but 4th's gradual climb can get annoying, especially with a head wind. Velma Ave is great.
OR
Cleveland Ave north to Essex Ave in Milo and north on Essex. Cross 11th Ave and continue north on Clara Ave. Cross 17th Ave and get on Velma Ave or the driveway for the historical society. This route is less efficient and kind of lonely as there is not much vehicular or pedestrian traffic.
Cleveland Ave is a great way to bike between eastern downtown and points north. The bridge over 670/RR is very nice and at night is car-free. Cleveland in general through Milo is good. I tend to use Cleveland whenever I am heading to CCAD, OTE, or points east. Plus there aren't a lot of lights to slow you down through the Milo Stretch.
The Tunnel under the tracks on Essex Ave is 300 feet long and pretty sweet.
On Clara Ave, there an Italian Bakery that makes fresh bread and donuts and desserts. It also sells some Italian Groceries and pastas. Its called Audinos.? Speaking of Bakeries, you pass the Krogers bakery on Cleveland that either smells like donuts or corn tortillas.
High St north to E. 2nd Ave over to Cleveland is a great connector, plus you get to see some cool ruins in Milo.
Biking to the Crew games sounds fun. Plus you can ripped everytime and not need to bother with those costly cars.