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New England road trip--long way to get there

We are thinking of doing this road trip end of May/beginning of June. I really want to visit NE, but don't want to leave our dog home for that long so we'd bring her with us instead of flying. We've done long road trips before but this would be about 20 hours longer than anything we've done. Just looking for any general tips/recommendations in these areas since we've never traveled further east than Illinois (not looking for any tips or stops prior to reaching Indiana). I can take up to two weeks off work so we would have 15 days to work with.

Highlights I'm trying to hit if possible:

Indiana Dunes NP

Cleveland Guardians baseball game

Lake Champlaign

Ben & Jerry's

White Mountains

Appalachian Trail day hike

Acadia NP

Freedom Trail

Boston Red Sox game

Mystic, CT

We're interested in outdoors, hiking, national parks, baseball, dog-friendly activities, camping/glamping (not bringing camping gear but we're okay with rustic accommodations), good food--all while trying not to spend a fortune :)

https://preview.redd.it/c0vnvqhqnivd1.jpg?width=1222&format=pjpg&auto=webp&s=58172d6a6ab27dd4325580c89d4b7b05b37c4f44
#travel #activities
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