Originally Posted by backontheroad

No one else seems to have replied with the winter road conditions along your route so I will do my best to provide what I know about your route. My winter commute is in Cottage Grove. My only rides into Woodbury and Newport would be after the roads are plowed for weekend rides or errands that can wait until the roads have been cleared and mostly on the county roads that have wide shoulders. Also I don't ride often in South St. Paul so I don't know what the plowing is like there.
The Bridge sidewalk along I494 I think would be plowed to comply with ADA.
The trails in Newport are plowed but I don't know when they plow them after it snow and if the Bailey hill trail is one that is plowed. I know Woodbury does not plow all its trails and it takes 3-4 days before the trails are plowed after a big snow. The plows used to clear the snow on the trails do not clear down to the pavement and leave about a 1/2 inch of snow. After a few snow falls the trails are quite rudded. Also the road plows throw snow chunks onto the trails. Remember this is Minnesota, the snow does not melt on the trails until spring. If you are planning on riding the trails in the winter a MTB might be the the choice.
Washington County clears its roads shoulder to shoulder. In the past they would have the county roads cleared by 6am but last year it wasn't until about 9am that all the roads would cleared. Woodbury takes longer to clear its streets then Newport and it could be a couple of days before all the streets are plowed. Also consider that you rarely will be riding in fresh snow unless your commute is a 3am. Once cars start driving on the road the snow on the side of the road will become dirty and "greasy" and while it is still snowing the plows will only be plowing the roadway and not the shoulders and you will be riding though deeper and dirtier snow on the shoulder.
For tire choice I would now choose at tire like the Nokian Hakkapeliitta.
On time it would take I agree with the 1/3 more time to ride in winter over summer is a good gauge but it only applies if the roads are cleared of snow. If you are riding through snow your speed could be as slow as a walking pace.
One last thing never ever ride up or down on the road on Bailey hill if it is snowing or there is snow on the road. There are many car crashes on this part of Bailey Rd. every winter.