Cold Wet Weather Gear

Deanna - I'm from a similar climate, so I hope this helps:

Running:  MANY LAYERS.  My favorite outfit is... dri-fit pants, pretty thin ones from Target, and maybe a layer under (tight cotton pants or shorts) if really cold. On top I wear a dri-fit top (short or long sleeve, depending) and a fleece jacket.  Once or twice I will wear a sleeveless singlet, long-sleeved Armour top together.  I think the fleece jacket is the key.  Fleece earcover or stocking cap and little cotton/poly mini gloves, which usually get really hot and I take them off.  Usually my headlamp too, since if I run after works it's dark.  This gets me happily through 20 degrees and above. 

Biking:  I'm still working on this, but two things that have helped are a waterproof shell that I can layer under and some totally awesome Pearl Izumi fleece lined cycling tights.  These are a MUST.  I wear a Headsweats skull cap and earband under my helmet, thankfully it's adjustable.  I still haven't found good gloves.  I usually tuck a scarf in around my neck, but am looking into a gator. 

So, I guess the key word today is FLEECE.  Good luck!  I wear this stuff often, so while expensive it's been worth it.

Edit:  I glossed over the "wet" part.  But, I've worn exactly that outfit while it's been snowing and it's fine.  That's the nice part about the fleece jacket.  It breathes, but keeps away most of the wetness.  The rain shell for the bike is a must, but you will get soaked.  I avoid that weather on the bike personally, but am trying to gather up my courage for this Fall/early Winter.  I was able to bike until December 9th last year, so don't put your stuff away too quickly!

For running, just tights (maybe polypro or even wool), a sweatshirt, and a thin shell vest. Layers.

For biking, I call it a stationary trainer. Or pretty much the same as a run, and ride the MTB off-road.

Cycling proper gear is key to getting out there when weather is bad/cold/raining. The best pair of tights I have a PI amphi type...water/windproof on the front and breathable normal warm tights on the back. I have the same fabric booties. Get a wicking skull cap for winter, plus nice wind/water proof gloves.

Last year I invested a lot in proper cycling gear for off weather and living in MA I rode every week all winter...it was grand! Favorite jacket is a Gore cycling jacket (bought at performancebike.com) nthat is wind/water proof and sleeves zip off. The wind is really what gets to me when it is 30 outside not the temp. I have other jackets that are windproof but more porus that work well when it is 45+.

A great source for cold weather bike gear for women is Team Estrogen...call and talk to them...I bought 4 jackets after talking with them tried them on and kept the Craft which is great but doesn't work as well in really cold weather..it was $200 but is perfect for 45+...wind proof mostly not water proof.

Running the wind isn't a factor as much and you produce more heat so totally water proof clothing that wicks makes me overheat. I have different vests/jackets I wear and normally wear cycling tights depending on the temp...sometimes my amphib ones when it is like 10, otherwise just plain or fleece lined. I bought a bunch of those $.99 gloves and my nose drips when I train outside in winter so I can wipe or blow snot rockets and just wash the pair.

Best socks I use for both running/cycling when cold are smart wool socks....really make a huge difference as cold feet stink.