We've got a week and a car heading up from NYC, with limited funds and a desire to spend some dollars in states that have approved Marriage Equality. The ideal trifecta for us is good food, beautiful countryside (with hiking), but also towns/cities including theater.
I'm vegetarian (lacto-ovo) and he eats absolutely everything. We both love adventurous eating, especially family-run places and foods of regions, countries, communities, ethnicities, cultures, etc. We've got only a little more than a week to plan, but the freedom to go anywhere that is in New England. The unglamourous, less expensive places almost always win over our hearts first. Oh - we also love bakeries, and basically all sweets.
I think there's probably 5 million itineraries that could be planned for this trip - if anyone cares to throw out ideas, know that they'll be greatly appreciated!