My daughter and her stroller did not have a happy start. She was born in November and I had a difficult labor. I couldn't take her out for walks for the first month after delivery, and then we had a frigid winter this past year. Whenever I would take her out, she would scream nonstop from the moment I put her in her bundling. She now just cries when the sun gets into her eyes and below is the series of steps for how we finally got to this point:
1) Assess your stroller. We have the Cameleon and also a Snap N Go to use with our Graco Snugride carseat. We also bought the Bugaboo carseat adapter which I recommend because the Snap N Go, while it folds quite easily is tough for long walks because the wheels just stink. Anyway, I digress. For the first few months, it's recommended to use the Bassinet feature on the stroller so your baby lays flat on her/his back. That's fine for most babies who are content to lie there and stare off into space but as soon as your little bundle starts to crave visual stimulation you are in a dilemma. My daughter hated being flat on her back and preferred the car seat as her stroller. She would still cry but would at least be manageable in a more seated position than flat on her back.
2) Use a portable mobile by Tiny Love (blogged about here) which saved many a walk for us. This can be clipped on to the canopy and is a wonderful distractor for many a baby.
3) Bring lots of pacifiers. If you believe in binkies, by all means use them here.
4) Distract baby while putting on layers of clothes. No baby likes to be restricted and bundled. I dress mine on my lap while bouncing her and that seems to do the trick.
5) Go for a mini run with baby and the stroller. My daughter started laughing hysterically as I ran her up a short hill. She momentarily forgot she was being taken outside for a walk and was calm the rest of the time.
If you are in a situation as I was where baby hates bunting, take heart. The weather gets warmer and it's one less hurdle to overcome.
For me, I also switched to the toddler seat on the Bugaboo as soon as I could - it has a recline position which works for infants (take care to still buckle them up) and baby could still gaze out much more than in the bassinet.