Re: Maine to Chesapeake Fall Passage
Days are getting shorter/ nights longer and colder. You should leave soon if you're going. As others have mentioned, make sure you have a reliable engine. If you haven't checked things like the impeller, alternator belt, changed fuel/oil filters etc. Check trans fluid. in awhile, I'd do so before leaving and carry some spares ( impeller, thermostat, antifreeze etc..) . I don't know what your fuel tankage is but you might want to carry an extra 5 gallons. And keep the tank full.
Cape Cod canal. By the time you get in the neighborhood of Block I, Cuttyhunk etc..you'll know how things are going, and can make a decision to go offshore to cape may or continue through the Race into Long Island sound. Weather, crew fitness etc will help dictate your decision. I'd stay flexible, and have multiple plans at your disposal. Know where all your bailout points are and what services are available to you along the way.
Entering a strange ( new) harbor at night can be stressful at a time when you are most exhausted... so if you're stopping I'd make sure to arrive with some daylight. As Chef mentioned, If you plan on 40 miles a day average, you can begin to plan around that.
Keep in mind that many marina services ( fuel docks, launches, showers, etc ) are likely on shortened, off season schedules now.
Make sure you have plenty of ready to eat foods to keep strength up. If you get in to any snot, you won't be doing much cooking.
If you sail through the night, have a thermos or two of soup, coffee, etc and some sandwiches ready before nightfall, and all the other safety systems..ie jacklines, tethers.
Eldridge will likely be your most used resource.. you need to be able to hit currents at the right time. Forcing a schedule is where people get in to jams, so I would remain flexible and adjust and adapt the schedule to the conditions, the ship and the crew..
Have a safe trip..