Guess I'm not seeing the problem. You're going to a show - I assume perhaps a concert at TCAN, which will be over around 11. And the commuter rail leaves at 12. Actually seems to work out pretty well. What am I missing?

Alan

Actually, I see that your train would not pass through Natick until after 1:00 a.m. That could be a lot of time sitting in a deserted place at night. If I were in your shoes, I'd rent a car. Google Maps (http://maps.google.com) will give you a map and verbal directions from your starting point to your destination (and back). Try renting a car from Enterprise, which has a desk in the Westin Hotel. You pick your car up and return it to the Westin driveway, which is just one block from the entrance to the Massachusetts Turnpike, which will take you to Natick. So you would not have to deal with Boston traffic that much. Also, I think that driving in Boston is really no worse than driving in most other big cities.

I agree I would rent a car as well. If you have good directions from google maps getting in and out of the city is fairly easy. Once you on the pike I-90 it is clear sailing to Natick.

Wouldn't renting a car and paying to park it overnight cost more than taking a cab one way from Natick to Boston?

I'd google the Natick chamber of commerce or use on-line yellow pages to find Cabs in Natick. You could save on cab fare by getting a ride to the Riverside green line stop, and taking the T the rest of the way back into town.