The autumn is wearing on, which means shorter days and colder temperatures. However, just because the winter is coming does not mean you need to entirely give up your vintage bicycle riding.
Your Basic Emergency Kit is Essential
A couple of weeks before the cold weather and dark conditions set in (often the changing of the clocks is a sign for those who ride in the evening), you should take a look at your riding kit and see if everything is in order. First, there should be some emergency supplies in there, in case you break down. This means a tire patch kit and levers, a flashlight, spare bulbs for your lights, a warm set of gloves, and maybe an adjustable wrench/screwdriver grouping. I use a large period saddle bag on my Raleigh sports to haul these things. I also have a brooks seat protector for wet or rainy conditions.The silver ring is a cuff clip for long pants, which I suggest you have if you want to keep your cuffs out of the chain. The best advice here is to think of what could go wrong in a ride (in a sane manner) and put in the stuff you'd need to remedy the problem. Also remember to carry your cell phone, in case you need to call a friend for a ride (if things get really bad). It's much harder to just "leg it" home when it's below freezing and dark outside.
Getting A Little Extra Light
Before riding in the dark, it's also time to check your headlight and taillight bulbs. Do a quick test to check light levels. Some systems put out nice light, others are a little anemic. A modern LED or halogen system running on good batteries will provide nice light. If you go period like me, my suggestion is an uprated bulb for a Dynohub or similar system.
The following website has some Dynohub-specific stuff that I found very helpful in selecting an uprated headlight bulb. It really does make a difference compared to the originals:
http://www.mbzponton.org/n2awa/bikes.htm
My bulbs are:
Head lamp bulb: "GH107", halogen, Screw-cap, 5V, 1.5W (0.3A)
Tail lamp bulb: "GV601", incandescent, Screw-cap, 6V, 0.1A, 0.6W
Both available from:
http://www.reflectalite.com/halogenpage.html
Again, check your system before you ride off.
It is also essential to have a rear reflector, which can be most helpful when you have cars behind you. Mine are period correct pieces, but still provide a degree of safety in being seen. A single reflector, alone, is not enough, but it goes a long way in being seen.
Priming the Pump
A frame pump or portable air pump for your tires is also a good idea. You can indeed find period-correct pumps too. If your bicycle has no frame pegs, you can buy nice frame pump clamps from various sources, usually on E-bay. On this Raleigh, I use period chrome clamps and a new pump that is a copy of the original. It is a good idea to refresh the rubber seals every so often with Trident Silicone Grease. Do not use a petroleum-based grease on the seals, always opt for Silicone. You can get it at Diver's or Scuba Shops.
Pumps even come in different sizes. This smaller aluminum Zefal pump is French and offers a compact solution for an even smaller pump. The smaller pumps tend to be a little more work because they put out less air, but it's still a good idea to have one.
Many old 3-speeds have an added advantage of a white strip on their rear fenders. The white combines with the rear reflector and the tail lamp on this bike to add some visibility.
Another period option is a "bottle" generator that rubs on the tire. I have had luck with Union brand Halogen dish lamps from the 70s and 80s, but this particular one is a two-pin dual beam light. They are very heavy and when engaged slow the bike down. However, they can provide a nice amount of light for the individual who is prepared to tinker with the system. I suggest them if you are interested in a low cost, period solution for your bike and are prepared to play around with setting them up properly. If you want an "easy" solution, avoid the vintage bottle types because you have to set them up carefully, and they can be a pain to pedal. Modern or brand new bottle types can cost a lot more, but are much better. However, for a period rider who is willing to maximize the system, a vintage bottle like this one below can offer a solution.
You can also buy a modern lamp with a retro look, if you want better light but a chrome bullet type. The lamp is made by Busch & Muller, and available at places like Peter White Cycles.
http://www.peterwhitecycles.com/b&m-hl.asp
It is worth noting that none of the vintage systems I detail here are
close to modern ones for output. Modern lamps offer impressive strength
and lower weight. You can always strap a modern light onto your vintage
handlebars for the winter and use that for awhile, at least until the
longer days return. However, even if you opt for an all-period system,
it is best to check your kit, your lights, and have warm, fairly visible
clothing for the ride.