A recurring question about cycling through Waukesha is "How do I get from the Glacial Drumlin to the New Berlin Trail?" While there are numerous ways through town, it really depends on your tolerance of traffic, hills, potholes and sense of direction(which is easily skewed when entering Waukesha). The easiest, safest and most efficient way I've found is College Ave. east to Hartwell then north to Lincoln Ave. which connects to the New Berlin Trail.
If you wanted to stop to eat, shop or stroll around the river downtown, heading north on just about any of the streets intersecting College- West Ave., Maple, Grand Ave., will take you to the heart of downtown. Taking Broadway Ave. in is easiest if your coming from the East.
The Downtown Rail Corridor
There is an abandoned rail bed made up of coarse gravel, unmaintained, that parallels Lincoln Avenue from Barstow to Perkins. It would be nice to see this trail improved as its a nice amenity to the neighborhoods it passes through. While I don't see it as the most likely route for cyclists passing through town, it is a safer alternative for those not comfortable riding on the streets or those who prefer a quieter ride through the east end of town. Definitely something to be considered.