Longfellows Wayside in Sudbury, MA has been operating since 1716.
Much of the Inn remains original and feels like it is 300 years old.
They have a small bar, and several small rustic dining rooms as well as updated rooms.
The food wasn't great, but it was a nice atmosphere - and I bought my "Original Boston Beat Pot" there.
The Inn also operates a Grist Mill. It's not even 100 years old (it was rebuilt to resemble the original)... but it's kinda cool looking.

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