you’re not going to get into any good restaurants on v-day, good luck with that one. you MIGHT be able to score a table at like 3 or 4 for something smaller/less known, but you’ll have a long drive ahead of you.
edit: i went to colden mill in boston last year without reservations, if you go early you might grab a table there they had a few open at around 6 pm coldenmill.com