The Load

Clothing
2 pairs of padded bike shorts. They're a bit large, hopefully that doesn't lead to horrible chafing that I've read about
2 pearl izumi bike jerseys
2 pairs of loose athletic shorts (covers awkward bike shorts so that I may walk around town comfortably)
2 pairs breathable wool socks
2 pairs underwear for sleeping, walking around. I will likely replace these during trip
2 t-shirts for walking around, also form a nice little pillow for sleeping. Also may replace these.
1 windbreaker/raincoat/poncho
1 pair of biking gloves
1 breathable cap

Shelter
Eureka Solitaire bivy tent w/rainfly
Compactable sleeping bag.
*Note: most nights I will try to stay with a host. This will probably be easier while in the east coast and midwest.

Toiletries
Toothbrush, toothpaste
Small shaving kit
Comb (this was the hardest decision while packing)
Soap, deodorant

Miscellaneous 
Utility knife
Bike multi-tool w/allen keys
2 spare bike tubes
Patch kit w/double patches and extra glue
Helmet (obvi)
Sunglasses
Small presta valve bike pump
Tire pressure gauge
SUNSCREEN
phonecharging cables
solar charger
a few books of my choosing *2016 edit: WHY would you bring heavy books???
portable camp stove
mess kit

*Note: I will likely buy food every few days at supermarkets. I'm finding there is little room left in the panniers for bulk food.