Greenfield sits where the Green River slides into the Deerfield, a short way above the wide Connecticut, in a part of western Massachusetts where valley farmland gives way to steep, wooded hills. It is a practical, brick-fronted town of about twenty thousand, a county seat that has weathered the decline of its old cutlery and tool factories and found a second wind with farmers' markets, small breweries and a lively main street. Few outsiders think of it as a destination, which suits the people who live here.
What makes it interesting to a rider is that it is the eastern gate of the Mohawk Trail. This stretch of Route 2 was a footpath used by Native peoples for centuries, and when the state opened it as a motor road in 1914 it was marketed as one of the first scenic highways in the country. It climbs steadily west out of the Connecticut valley, with long bends, a narrow ledge above the river at Shelburne Falls, then the tighter, steeper section over the mountains beyond. Cross it in autumn and the maples set the whole hillside burning, but the road is jammed with leaf-watchers, and you may spend more time looking at brake lights than at foliage. Early on a weekday in September is better.
Close by, there is plenty worth stopping for. Shelburne Falls has the Bridge of Flowers, an old trolley bridge planted with gardens, and downstream the river has scoured glacial potholes into the rock, great round bowls ground out by stones swirling in meltwater at the end of the ice age. Turners Falls, to the east, has a big dam and a quiet canal, and nearby Old Deerfield preserves a village street of eighteenth-century houses where, in 1704, a French and Native force attacked the English settlement and marched captives north to Canada.
Greenfield has fuel at several stations along the main road and a good range of diners and cafés, and the local farm stands sell apples, cider and maple syrup. After the heat of the valley, the hills feel several degrees cooler, and in winter the high sections of Route 2 can ice up quickly, so check the forecast before you climb.