This is the shortest route around Candlewood Lake in Connecticut. Candlewood lake is the largest lake in the state in Connecticut and New-England's largest man-made lake (https://en.wikipedia.org/wiki/Candlewood_Lake) and travels through 5 towns/Cities (Danbury, New Fairfield, Sherman, New Milford, and Brookfield). This is a popular biking route but to my knowledge, no one I know has attempted to run around it. In a community rich with ultra runners, this needs to be a more popular challenge. It is entirely on roads and the elevation change is not for the faint of heart. On this route, you run are treated to beautiful aerial lake views, and you run through quaint CT towns, past vineyards, and along the water for long stretches. The route may be done in either direction.
This link (http://berkshirehiking.com/drives/candlewood_loop.html) describes much of the route except it skips over a stunning portion of the south end of the lake through Danbury as you hug the coastline for 6 miles. This section connects between Candlewood Lake rd in Brookfield and Rt 37 (mention of the federal correctional facility).
This is easily the most navigable and enjoyable 55km ultra distance on roads in the area.