Originally Posted by
Analise
When you leave Freeport and get back on 295, ignore Exit 10 that tells you to get back to the Maine Turnpike. That's totally out of the way and they want you to go back to paying tolls. Stay on 295 and take it to the end (exit 1 is the Maine Turnpike). Kittery is then about 35-45 minutes south of Portland.
Small correction. If you were take Exit 11 (Exit 10 is for Bucknam Road, Falmouth), you could get on the Maine Turnpike southbound and it would not cost any different than taking 295 to the end ($1 for a passenger car either option). And in fact, there is a TON of construction happening on 295 through the Portland area right now, so I would suggest you take Exit 11 rather than drive through downtown Portland unless you have a stop to make in Portland or South Portland.
Now for one of the best kept secrets in Maine... On the way back North, you will want to get back onto 295, but DO NOT take exit 44 (they charge a toll at exit 44)... take exit 45 instead which puts you on another little divided highway. Don't take the first exit there (for the Mall area), but take the second exit, and voila, you've gotten back on 295 without paying a toll. Only takes about an additional minute, but you've saved a buck!