Travel
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What to do? We'll be heading up next weekend for our anniversary. We've got lodging and food all figured out, just looking for stuff to do during the day. When we went last year, we did go to the Normal Rockwell Museum, and while it was really cool, we don't feel the need to go back again.
Re: The Berkshires
Clearly I'm too late, but a hike (or bike ride) up Mt. Greylock would be a great challenge for you (I know you are on H&F a lot), if any of the mountains will have their alpine sleds up (might be too early) might be fun.
What did you end up doing? A walk through Lennox is also nice and relaxing as well.