Keene has the widest Main Street you are likely to see in New England, and the town is justifiably proud of it. The street is broad enough that it is often described as the widest paved main street in America, and with a white-steepled church at one end and the old brick storefronts down both sides, it creates a feeling of space and leisure unusual in a New Hampshire town. The Ashuelot River winds through the area, and Keene State College keeps the downtown lively.
For many people the town is best known for its pumpkins. For years Keene held a Pumpkin Festival that broke world records for the number of jack-o'-lanterns lit in one place, with tens of thousands of carved pumpkins stacked on scaffolds along the main street. The festival has since moved on, but the town's fondness for the autumn season remains. Keene is also called the Elm City, a nod to the trees that once lined its streets before the elm disease took most of them.
As a starting point for a loop around Mount Monadnock, Keene is hard to beat. The mountain, about 3,165 feet high, rises abruptly from the surrounding hills to the southeast and is often cited as one of the most climbed in the world, and the surrounding villages of Marlborough, Dublin and Jaffrey are charming. Route 101 runs east through the hills, with moderate curves and a few climbs, while the back lanes offer slower, narrower stretches among stone walls and open fields.
Keene is a proper small city, so you will find all the usual services: fuel at several stations, supermarkets, restaurants and hotels. It makes a handy place to start, finish or just refuel. The best seasons are autumn, when the whole region is gold and red, and late spring, when the trees come into leaf and lilacs bloom. Summer is warm but pleasant, with the odd thunderstorm, and winter brings snow and ice. Traffic is light outside the town itself, though weekends in leaf season can bring crowds on Route 101 and around the mountain, so patience and an early start are valuable.