Princeton sits high in central Massachusetts, in the hills below Mount Wachusett, and it feels farther from Boston than the forty-odd miles of the map. The town is a scattering of old farms, stone walls, white churches and woods, and at around three hundred metres it is cooler than the lowlands, with an early autumn and snow that comes sooner and stays longer. A well-known ski area and a state reservation share the mountain, and in autumn the hillsides are among the brightest in the region.
Mount Wachusett, at about 611 metres, rises alone from the rolling country, and on a clear day gives views to Boston's towers in the east and the peaks of Monadnock in New Hampshire to the north. The Wachusett Reservoir, a huge lake to the east, supplies water to much of eastern Massachusetts, and its shores are protected, so the area around it is quiet woodland. A summit road, open in season, winds up the mountain, and the hiking trails are well kept. The Midstate Trail runs through the town.
The riding is pleasant rather than dramatic. Roads such as Route 62 and Route 140 run through the hills in smooth, rolling bends, with tree-lined stretches, small villages and farm stands that sell cider doughnuts and apples in fall. Surfaces are mostly decent but frost heaves can be rough in spring, and traffic can be heavy on weekends in October, when leaf-peepers fill the roads. Sunrise from a hilltop pull-off is a good start to a day, and the smell of woodsmoke carries on cool evenings.
Princeton itself is small, with a general store and a few places to eat, so fuel is better found in Sterling, about ten kilometres away, or in Holden and Fitchburg. Rain can come quickly, and mist often hangs on the mountain in the morning. The best months are May and September, when the roads are quieter and the air is clear.