Washington Depot is essentially the model for the town in GG. They have signs and Tshirts about it and the cookbook is available in the bookstore. It's cute and all, but not much to actually do, as far as I can tell.

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Litchfield has a pretty cool downtown area that is worth checking out with gift shops, antiquing, art stores, coffee shops and plenty of low-pressure browsing. A favorite of mine is the kitchen supply place (I love cooking and kitchen gadgets).

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The museum associated with Yale is still free, as far as I know, so even a 15 minute scan is worth it. https://artgallery.yale.edu/.