NY9N from Lake Placid to NY185
NY185 over the Crown Point Bridge to VT125. Omelettes at the diner—bring your own sa-om.
VT125 through Middlebury to US7 south
US7 to VT125 again
VT125 to Hancock
VT100 south to US4 near Killington
US4 to pickup VT100 south near West Bridgewater
Rt 100 to VT103 near Ludlow
VT103 to US5 south
US5 to Rockingham St then over the bridge to North Walpole and NH12
NH12/123 to Keene
An alternative route would be to cross over the Crown Point Bridge then take VT17 straight to Waitsfied to catch VT100 south from there. You'll ride over Appalachian Gap to get to Waitsfield—a few curves in that mountain road to wake you. VT17 also will take you through Granville Gulf—a short but sweet ride.
Most of this travels through mountains, farmland and small towns. The largest town you’ll visit is Middlebury but it’s compact and beautiful. Ludlow is a fair-sized ski town but smaller than Middlebury.
I'm usually unconstrained by a schedule when I travel, so this itinerary meanders, but I can assure you this could be a colorful journey with enough twists to keep you awake. I've ridden it many times when heading to Amherst and Northhampton.
Keep in mind, Vermont road infrastructure as been severely damaged in many areas, starting with the July 17, 2023 flood. Recovery has been hampered by another severe flood that occurred July 17 this year, and several other torrential events besides. There has been heavy rain off and on all day here near Waterbury, VT. Half the upper town road to our place has slumped downward toward the gorge for about 100'. It's picturesque. It's the first gravel cravasse I've needed to navigate up here. Although road and property damage is widespread throughout Vermont, it is often localized by the microclimates developed among the mountains. The evening forecast tonight is for torrential downpours measured in inches per hour in some areas from north to south.
When traveling here,
511 can be helpful to determine if your route is possible, but it only shows State road construction not town road damage. If you go cross-lots using Class 3 gravel town roads as connectors, you might get in a mess. The route I’ve laid out is paved state and a couple of federal roads, not that they're immune to undermining and collapse by flooding but more money is available sooner to fix them.
Perhaps by leaf-peeping time when you hit the road, most of the damage will be mitigated but there’s no telling when if these heavy rain events continue into fall.
It's an adventure.