Region: Southern Vermont — Windham & Bennington Counties Distance: ~105 miles Time: 2.5 - 3.5 hours riding Surface: Paved (numbered state routes throughout)

Start in Londonderry and head south on Route 100. The road follows the West River through South Londonderry and Rawsonville, the valley narrowing as you move toward Jamaica. From Jamaica, Route 100 continues south — the terrain opens briefly before the road works through Wilmington along the Deerfield River valley.

At Wilmington, pick up Route 9 west. The road climbs through Woodford and over the Green Mountains before descending into Bennington. The crossing is the high point of the ride — the summit cuts through dense forest before the mountain drops away and the Bennington valley spreads out below.

In Bennington, Route 9 meets Route 7 north. The road runs up the western edge of the state through Manchester — long straightaways, the Taconic Range to the west and the Green Mountains to the east. More open and faster-moving than the southern segments.

From Manchester, pick up Route 30 north and then Route 11 east back through Peru and Bromley toward Londonderry.

Surface notes describe road type, not day-of-ride conditions. This route follows numbered state and US routes throughout and is likely fully paved. Road conditions and surface transitions can change with weather, maintenance, and season — these notes reflect road type, not day-of conditions.

Use this information to decide what fits the ride you have in mind.

If you know roads or routes worth building a ride around, hit reply and tell me about it.