If you're thinking of upgrading some of your core gear, consider starting with a new sleeping bag. In recent years the ultralight wave in camping equipment has created a space-race mentality among manufacturers to engineer ever-lighter, tiny-packing bags. A small-packing bag can save a surprising amount of space in a pannier or on a rack. Down bags compress the smallest, but you need to be hyper-vigilant about protecting it from moisture. If you carry down, stuff it into a plastic garbage bag after you crunch it into its stuff sack. New synthetic bags, particularly those that use new insulations such as PrimaLoft® Sport or Polarguard® Delta, compress surprisingly well and provide a respectable level of warmth for a modest weight. The key advantage for using a synthetic bag: It dries out much, much faster than down. In a pinch, you can even sleep in a damp synthetic bag (it will still insulate) and dry it out with body heat. Consider bringing a bag liner, too. It can boost a bag's comfort rating by 10 to 15 degrees, help keep a bag clean, and, on balmy nights at low elevations, can be used alone.
You've heard it before, but you can never hear it enoughplan to pack according to weather. A three-day tour through arid terrain will differ greatly, climate-wise, from a pedal through rainforest-lined asphalt. Also, while you do have those panniers to carry your load, still aim for the less-is-more approach; it'll increase your balancing ability, reduce weight drag, and give you spare room for that must-have purchase (perishable or otherwise) that you encounter mid-route, especially if you're weaving into small towns while touring. For the heavily-laden, also consider one of the new towing trailers that you can attach to your bikethey even have some out there now that can handle most singletrack routes (albeit slow-going).
All-Season Clothing
Helmet
Jersey
Wicking tees
Wicking long-sleeve top
Arm and leg warmers
Fleece vest/jacket
Cycling shorts
Wicking underwear
Soft-shell pants
Cycling shoes
Off-bike footwear
Wicking socks
Padded cycling gloves
Non-cycling convertible pants
Wet- or Cold-Weather Add-Ons
Waterproof/breathable jacket and pants (hard or soft shell)
Waterproof/breathable gaiters
Weather-resistant gloves or overgloves
Goggles
Helmet liner, skullcap, or stocking cap
Mid- or expedition-weight base layers
Travel Gear
Handlebar bag (with clear map slot)
Front and rear panniers with rain covers
Seat bag
Hydration pack
Water bottles
Headlamp
Batteries
Headlight/taillight
Rearview mirror
Bungee cords/compression straps
Accessory cord (25+ feet)
Lock
Maps/guidebooks
Cyclometer
GPS
Cell phone/PDA
Watch with altimeter and alarms
Tools/Spare Parts
Spare tubes (2+)
Spare tire
Spare spokes (6+)
Bike-specific multi-tool (with spoke wrench, allen wrenches, screwdrivers, etc)