Avoid driving out of Boston up to Maine on a Friday, traffic is god awful (same is true coming out of NYC to Connecticut though).
If you're a beer guy, driving up would allow you to hit Treehouse -> Trillium -> Maine Beer Co.
climb Cadillac Mountain, view is amazing.
View attachment 125029
Yes. Be very careful of Friday after 4pm. You can literally sit in traffic for 3 hours to get from the Mass border to the 1st Maine tolls. Normally about a 30 minute ride. Parking lot from Maine Tolls, to NH tolls, that can extend into Mass.
Should you bypass that section, using rte 1, expect backup as well.(about an hour and half, and 100 lights). Rte 1A is a nice ride, along the ocean, but that takes forever, too.
Used to do this ride, all the time. NEVER on a Friday night, unless you budget up to 3 hours extra. And that's not even considering the NORMAL rush hour traffic outta Boston, that often turns 1 hour, into 2 or more.
If you fancy Amtrack, there is another option. There is the Nor'Easter outta Boston, to Portland Maine. It's not a Subway style train, it's nice. Also, you need to buy tickets for it, well in advance. It's the preffered method of travel for many that work in Boston. Sold out on the weekends, as well, because traffic can really suck. Not to mention the $30 plus Boston parking, pays for the ticket, and the train has a beer car.;-)