That sounds like a pretty awesome trip! Make it a circle stopping in other places on your way there and back and just stay there for a couple of days.
this post was submitted on 27 Feb 2025
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South Maine is pretty nice. We stayed at a bed and breakfast in Kennebunkport. Great food and hard to beat the scenery.
Vermont looks pretty nice too, but no personal experience there yet.
What do you like to do in your free time? That will help give us an idea of where to recommend based on what is available to do & is still in reasonable driving distance for you.
Like history? Consider Gettysburg, Manassas, Fredericksburg, Yorktown, or Williamsburg.
Like wine? There are dog-friendly vineyards, breweries, and distilleries all up and down Virginia's wine country. Look into Leesburg or Charlottesville as a central base.
Annapolis, MD and Alexandria, VA are both very dog friendly and have adorable "old town" sections with delicious food and shops. These towns are also great if you like photography.
But if you have a portable hobby like painting or reading or even gaming on a console, a little island all to yourselves for a week where the dog runs free and you entertain yourself with your hobby sounds like heaven.
I pretty much just game and work, but history is interesting. Gettysburg does seem interesting but I understand that the battlegrounds aren't dog-friendly so that could be tricky.
New York city is just down the way. Virginia Beach isn't that far of a drive. We are going to Cedar Point once it opens.