While the Bear Creek Greenway doesn't cross Ashland (except in proposals), the city offers a plethora of bike routes that will get you from here to there.
At the city's wastewater treatment plant, cyclists can choose to abandon the trail and follow the plant access road to Oak Street, which offers an easy route into town that avoids hills but might be a bit busy for youngsters or others who like to avoid traffic.
Stay on the greenway and at the Ashland dog park, ride or stride right on to Helman Street, which provides a family-friendly route past Helman Elementary School. At Hersey Street or Van Ness Avenue, head one block east to Water Street, which will deliver you right to the Plaza and the heart of downtown. (It shouldn't be hard to find a parking place for your bike in the rack on the Plaza, if you fancy a meal or a bit of shopping.)
Greenway users who want to travel all the way across Ashland will find a great city trail that runs along the railroad tracks. From Helman Street, Van Ness usually provides a fine link to A Street, but construction has that area looking a little rough, so B Street is a better choice to head eastward.
Then, duck down Fourth Street to a quiet access street to private parking lots behind A Street buildings. There's little traffic here so it's good for walking or biking with kids and leads directly to Railroad Park, which has a playground, basketball court and picnic shelter.
This trail crosses city streets, so people cruising along the trail must stop and check for traffic. At North Mountain Avenue, it's a short jaunt, and all downhill, to North Mountain Park, with its ball fields, nature center and more.
The trail also swings right by Garfield Park, home to the zero-depth water park for splashy summer fun, a playground and enough open space for touch football, volleyball and even the occasional kite-flying outing.
The trail crosses the outer reaches of the Southern Oregon University campus and passes between Walker Elementary and Ashland Middle schools. It also skirts the edge of Hunter Park, which has eight tennis courts, ball fields, a playground, picnic areas, restrooms and the Daniel Meyer Swimming Pool and the Senior Center. The city's outdoor pool is open Memorial Day weekend through Labor Day weekend.
A quiet stretch of trail runs through Mountain View Cemetery. At the cemetery's edge, Shamrock Lane provides a quick link to a large gravel parking lot. The trail continues under Ashland Street and on to Tolman Creek Road.
Serious cyclists follow Ashland Street east until it becomes Highway 66 and ultimately delivers them to Emigrant Lake and beyond.