City Escape: Boston, Massachusetts

City Escape: Boston, Massachusetts

The White Mountains of New Hampshire and roads like the Kancamagus Hwy get all the attention. But there are some fine roads and thinly-settled areas to explore when heading from Boston, MA, to southern New Hampshire.

The region is filled with quiet roads to nowhere and crossroads with little more than a post office, church, and country store. The land rolls gently and the roads are rarely straight. And at nearly 3,000 feet, Mount Kearsarge is a monadnock—a rocky hill or mountain rising from an otherwise flat landscape. It’s a good destination for a weekend ride.


Approximately 208 miles

Lunch Stop

Lindy’s Diner in Keene is a classic New Jersey-style diner where breakfast is served all day. Other options in Keene include Mexican (Margaritas) to Thai (Thai Garden) to vegan (Farm Cafe). Find Lindy’s at 19 Gilbo Ave, Keene, NH, (603) 352-4273.

Points of Interest

Contoocook Railroad Covered Bridge

One of many covered bridges in the area, the Contoocook Railroad Bridge was built in the 19th century. It carried rail cars over the eponymous river until 1960. The nearby Contoocook Railroad Museum in the old train depot tells the story.

Mount Kearsarge

A short, winding mountain road carries you to the top. Enjoy the views from the parking lot or take a short, steep hike to the bald peak, climb the fire tower, and get a commanding, 360-degree vista over 2,000 feet above the surrounding lands. On a clear day, you can even see Boston.

Keene, New Hampshire

Downtown Keene has a number of restaurants to choose from and a farmers’ market on weekends. While there, you can also explore the history of Keene, all the way back to its original settlement in 1736 and beyond.

Mount Monadnock

At 3,170 feet, Mount Monadnock is the highest mountain in southern New Hampshire. Emerson and Thoreau wrote about it and the views from the bare peak are stunning. Local legend says that the peak was lit on fire to drive out a pack of wolves. You’ll have to hike to the top, though.