A couple quick thoughts here:
Sounds like a great trip, as a 57 year old whose odometer is half way towards its next click, you haven't reached old fartdom until you start trying to make offshore passages just to show that your not an old fart.
On a more serious note, the weather can be pretty nasty and unpredictably changeable that time of year, and a Catalina 30 isn't exactly my idea of an ideal boat for wrestling with a mid-fall Atlantic gale.
If I were going to try that trip in a Catalina 30, I would make sure that I had a really high quality 100% or so jib, a less than 90% jib in addition to the more standard 135% genoas that these boats seem to sail with more often. In heavy conditions you cannot furl in more than 10-15% and expect to have a decent heavy air sail shape. You might also add safety ties to your headsails so you can safely make a headsail change in heavy going. Netting forward helps as well.
I would also make sure that I had mainsail and boom set up for two reefs with a good reliable two line reefing system for each. I would replace or at least check the plastic slugs on the mainsail as these seem to wear out without warning and let the sail peel away from the mast at inopportune moments.
Check your standing and running rigging carefully and consider replacing your standing rigging and any questionable running rigging. Your boat is probably at the age where the standing rigging has passed it's safe useable lifespan (normally quoted at 10 to 15 years) and I would bet your boat still has its original standing rigging.
I would clean the fuel tank bottom and make sure that you had clean fuel filters and knew how to use them.
If you make the jump offshore and had a favorable wind, its maybe a 6 day trip offshore but quite a few weeks if you chose to run down the ICW.