Ali and I took the 50-mile drive to Chimney Bluffs State Park (7700 Garner Rd., Wolcott) for the afternoon with our dog, Lucy. The park is really nice and interesting: a moderately challenging [and, at this time, incredibly muddy], 1-mile trail that climbs to the top of alien-looking "earthen spires". It's a peculiar treasure around here: I have yet to mention it to someone who already knew about it.
On the way back, we stopped for dinner at Orbaker's Drive-In (4793 State Route 104, Williamson) which is this great burger joint that's been there forever. Ali knew of it — being an aficionado of sauce-laden burgers — and rates it very highly. While not quite worth a trip from anywhere, it's not that far if you're already out 104 on the east side.
Try Fat Boy's Drive In in Brunswick, ME on the way to Acadia–authentic place from the 50's