Madison Road Biking

If you're looking for a weekly informal ride (and have Wednesday nights free) - http://www.wnbr.org/

You can also ride your road bike through the University of Wisconsin Arboretum.

Bike Paths: 

Capital City State Trail

The Capital City State Trail in Madison is both a commuter path and a recreational biking path. The trail cuts through the south side of Madison, from just south of Lake Monona west towards Verona and the Military Ridge Trail through the Capital Springs State Recreational Area. If you are using the trail through the state recreational area, you will need to purchase a state trail pass.

17.00miles

Lake Monona Bike Path

What's the premiere place in Madison to go for a bike ride? You'll get some disagreement, but most people, serious cyclists or not, will say the bike path around Lake Monona.

The bike path is 13 miles long, and is paved, but is not offset from traffic the entire way around the lake. Quite a bit of the way is on bike lanes of relatively busy city streets. Do not ride on the sidewalks in the city of Monona, as periodically the police issue tickets in the areas where bicycles aren't allowed on the sidewalk.

13.00miles

Glacial Drumlin Trail

The Glacial Drumlin Trail is a 52-mile trail that connects Cottage Grove, just east of Madison, with Waukesha, west of Milwaukee. The western 39 miles of the trail are wide, crushed limestone - the eastern 13 miles are paved and suitable for road bikes or inline skating.

Like many Wisconsin rail trails, you will need to purchase a state trail day use or annual pass if you plan to bike, cross country ski, or inline skate. Hiking the trail does not require a trail pass.

52.00miles
Bike Rental: 
You can rent hybrids, mountain bikes, or bike trailers from Machinery Row Bicycles - http://www.machineryrowbicycles.com/