Tara says:
I would move just outside of Connecticut and try Keene, New Hampshire... I lived there and not only does it have a long Main Street lined by oak trees, it also has a gazebo in the town center with a huge white steeple church behind it. Main street has a local diner called Timoleon’s, candy store, record store, pizza shop, etc. During autumn they have a huge pumpkin festival and lined the entire Main Street with pumpkins covering every inch and leave them for days and decorate the lamp posts with garlands of autumn leaves. The town smells of pumpkin spice and apples during autumn. During winter all the lamp posts and trees are lined with white twinkling lights and its pretty magical when it snows. Winter festival includes carolers in the gazebo followed by Santa and rides up and down Main Street in horse pulled sleighs. It's as close to Stars Hollow (on Gilmore Girls) as you can get IMO. I recommened googling “Keene, NH christmas” and Keene NH autumn or pumpkin festival.
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