Did a 5 day Vermont/New Hampshire loop last October (flew into Boston, drove up) and wanted to share since I spent weeks planning this. Spoiler: some things were even better than the photos and some were overhyped.
The good: Stowe, Vermont was absolutely stunning. Peak foliage, cute town, incredible cider donuts at Cold Hollow. Worth every minute. The Kancamagus Highway in NH was also jaw-dropping, we timed it perfectly with the colors.
The meh: Woodstock VT was pretty but felt like a movie set. Very manicured and full of day trippers. We couldn’t find parking at noon. The covered bridges were cool for a photo but not worth driving 30 minutes out of the way for each one.
Biggest tip: go on a weekday if you can. We did Saturday through Wednesday and the difference in crowds between the weekend and Tuesday was night and day. Also book accommodation months ahead, everything decent was sold out by August.
Total cost for 2 people, 5 nights: about $2,800 including rental car, gas, hotels (mix of B&Bs and one nicer inn), and eating out every meal.