Continued commuting by bike during the winter pulling a trailer with a child in it can be seen as an impossible proposition for some riders, but we are here to help you climb the mountain, summit, and hike home.
Clothing:
Everyone involved must me dressed for success. Acquiring proper outdoor winter gear is what the fine folks at the Moose's Tooth do and for our purpose we will leave those questions to a visit with them at the store.
Bicycle and Trailer:
Preparing the bicycle for winter use usually involves having proper tread or ice tires put on the bike for extreme conditions. Maintaining the bike and having the shifting systems and braking systems in fully functioning form is very important. Like any other commute we start our ride with the ABC QUICK CHECK. The A is for Air. Do my tires have the proper inflation and are they holding air and is the tread in proper form? B is for Brakes! Are the brakes properly adjusted and can and will they stop the bike? C is for Chain or drive chain. Is the chain lubed and does the drive train appear to be clean and functional? Quick Check is ensuring that everything on the bike is in place and working. No loose bolts, racks, skewers, nuts etc. By going through the ABC Quick Check before riding you can ensure that you will have a fully operational bicycle each and every time you go out into the cold to commute.
If you are pulling a trailer, then it is important to check all of the quick releases and attachment points. The arm of the trailer to the axle should be checked at least weekly. Clean it out too while you are at it so that mice etc don't get to those cookies that junior dropped under the seat.
Warm, Warm, Warmer!
Keeping children warm and protected is the most important part! If you have a mechanical failure there has to be enough warmth regardless of how long it takes you to fix the bike or walk it somewhere. If you are going through the ABC QUICK CHECK then you shouldn't be as prone to these problems, but preparation is always key. An extra blanket or jacket in the trailer is a plus. Lining the bottom of the trailer with a thermal barrier is a good idea too. Damon and I usually use a therm-a-rest camping pad because it has a relatively high insulation value for the weight....and it is something that we already own...so use your resources as needed. Food and drinks are best to have with too. Cold winter mornings and windchill increase your need for caloric intake. Hot coffee, tea, and yummy high calorie cookies and baked goods are great to have on board. When our child was 8 months old, i would warm a dromedary bag and put it in the trailer as a kind of heater. I also built in an internal temperature monitor so that I would know exactly how warm it was inside the trailer.
Butch
To help illustrate what Butch wrote I shot some photos of Weston and I on our commute. This mornings ride was 34 and drizzly, but Weston was warm and comfortable enough to nap for most of the ride to his preschool.
Clothing:
Everyone involved must me dressed for success. Acquiring proper outdoor winter gear is what the fine folks at the Moose's Tooth do and for our purpose we will leave those questions to a visit with them at the store.
Bicycle and Trailer:
Preparing the bicycle for winter use usually involves having proper tread or ice tires put on the bike for extreme conditions. Maintaining the bike and having the shifting systems and braking systems in fully functioning form is very important. Like any other commute we start our ride with the ABC QUICK CHECK. The A is for Air. Do my tires have the proper inflation and are they holding air and is the tread in proper form? B is for Brakes! Are the brakes properly adjusted and can and will they stop the bike? C is for Chain or drive chain. Is the chain lubed and does the drive train appear to be clean and functional? Quick Check is ensuring that everything on the bike is in place and working. No loose bolts, racks, skewers, nuts etc. By going through the ABC Quick Check before riding you can ensure that you will have a fully operational bicycle each and every time you go out into the cold to commute.
If you are pulling a trailer, then it is important to check all of the quick releases and attachment points. The arm of the trailer to the axle should be checked at least weekly. Clean it out too while you are at it so that mice etc don't get to those cookies that junior dropped under the seat.
Warm, Warm, Warmer!
Keeping children warm and protected is the most important part! If you have a mechanical failure there has to be enough warmth regardless of how long it takes you to fix the bike or walk it somewhere. If you are going through the ABC QUICK CHECK then you shouldn't be as prone to these problems, but preparation is always key. An extra blanket or jacket in the trailer is a plus. Lining the bottom of the trailer with a thermal barrier is a good idea too. Damon and I usually use a therm-a-rest camping pad because it has a relatively high insulation value for the weight....and it is something that we already own...so use your resources as needed. Food and drinks are best to have with too. Cold winter mornings and windchill increase your need for caloric intake. Hot coffee, tea, and yummy high calorie cookies and baked goods are great to have on board. When our child was 8 months old, i would warm a dromedary bag and put it in the trailer as a kind of heater. I also built in an internal temperature monitor so that I would know exactly how warm it was inside the trailer.
Butch
To help illustrate what Butch wrote I shot some photos of Weston and I on our commute. This mornings ride was 34 and drizzly, but Weston was warm and comfortable enough to nap for most of the ride to his preschool.
Damon
Getting trailer ready, above is the sleeping pad wrapped in a blanket
A winter cover for a car seat. I like this b/c it zips around the legs like a sleeping bag
Rear flashing light with reflector and two small flashing lights on both sides of the trailer 
Getting Weston ready 
Filling a bottle with very hot tap water
All layered up and ready to go!
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