I don't know if I can help too much. We spent 10 nights or so in Vermont, one of our very few spring holidays (2016?), splitting time between Woodstock and Burlington. These two lovely rentals, which are still going strong (though I don't remember them being so pricey, even taking inflation into account):
https://www.vrbo.com/en-ca/cottage-rental/p616376vb?adultsCount=2&noDates=true&uni_id=1163885
https://www.vrbo.com/en-ca/cottage-rental/p3608509?adultsCount=2&noDates=true&uni_id=3622941
Woodstock is a smallish, quaint place, if the description quaint can still be used without soliciting derision. Billings Farm and walking trails are close by. A lot of hiking, and more driving than usual along country lanes, stopping off for long lunches.
Burlington, which has a pleasant waterfront and a large pedestrain area, has more going on. If you are there in August there will be opportunities for theatre there and just down the road in Middlebury. During certain periods, street perfomers. Boat rides on Lake Champlain. Try to grab a meal at Vermont Pub and Brewery, which brews excellent beer. I used to be a keen homebrewer. The man who opened the pub, Greg Noonan (deceased), is a bit of a legend in homebrewing circles, and was one of the brewers who paved the way for the microbrewery revolution in the USA.
Close by, Montpelier is really worth a visit: a historic town with lots of eateries. Stowe has a few famous resorts, including one belonging to the Von Trapps. Splendid scenery everywhere. Try this: https://vermontvacation.com/
For small city North America, you can't do any better than Old Quebec. I think the main music festival takes place in July but there is usually something going off with street perfomers during the whole summer. Many years ago we stayed here and were very happy with it: https://www.manoiresplanade.ca/en
Just around the corner, Cafe de Paris had great food and quiet entertainment (singer/harp player).
Lunch and dinner cruises from the harbour. It has its own Notre Dame cathedral. Make a day trip to Sanctuaire Sainte-Anne-de-Beaupré, Montmorency Falls and Ile d'Orlea.
I once took a youth soccer team to Montreal but don't remember too much about it, mainly a case of grabbing a bite to eat in the evening, though the old core has a certain flair to it.