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Ideas for New England Road Trip in September with Toddler

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My husband and I are thinking about taking a 10-14 day trip to New England with our son the first two weeks of September. He will be almost 2 at that time. We would fly into Boston but from there I am not sure whether to go north or south (or both!), it sounds like there are so many great places to explore. Ideally we'd like to avoid changing hotels every day and maybe have 3 or so bases that we can stay in for 3-4 nights and explore and do side trips from. Any recommendations? We love great scenery, going on walks, cute towns, historic architecture, and we would also like to spend at least a few days in a beach town. Places with child-friendly activities (children's museum, playgrounds, etc.) would be nice too. I appreciate any suggestions! Thanks!

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