Not my neighborhood, but the Vermont 200 on 100 goes right through Waterbury. Therefore, she could just head North towards the Canadian border on Hwy 100 and turnaround at 40 miles (or hit the border for a good photo op at 54). Here’s the route / org - http://100-200.org/
Check out the road race stage of the Green Mountain Stage Race. Has a bit of everything… excellent gradual descent through Granville Gulf with waterfalls along the way, two gap climbs and then a descent right back into Waitsfield which is very close to Waterbury. Feel free to message me for more ideas. I’m pretty familiar with the area.
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