Okemo Valley

No road or mountain vista gives quite the sense of place, however, that you’ll get simply by lingering in these 11 picturesque towns. Each is unique in its offerings—from outdoor sports to historic attractions to fine food and drink—yet all share the pace, and the peacefulness, of an earlier era.

Among the most notable people to fall under the spell of the Okemo Valley was Calvin Coolidge, who in 1923 was sworn in as the 30th U.S. president at his family home in Plymouth Notch. He returned to the tiny village often during his life, and now rests in a hillside cemetery that’s part of one of the nation’s best-preserved presidential birthplaces. Covering more than 600 acres, the President Calvin Coolidge State Historic Site welcomes visitors to the Plymouth Notch that Coolidge knew, complete with 19th-century farm buildings and Vermont’s oldest one-room schoolhouse.

The Coolidge story touches another piece of Okemo Valley history: cheesemaking. The Plymouth Notch cheese factory founded by Calvin Coolidge’s father is home to the award-winning Plymouth Artisan Cheese, whose cheddar draws on an 1890 recipe. Across the valley, long-established cheesemakers like Mount Holly’s Crowley Cheese (1824) and Grafton Village Cheese (1892) and modern ones like Chester’s Jersey Girls Dairy keep this delicious tradition alive.

More culinary heritage is in the spotlight during one of the region’s favorite autumn events, Mount Holly Cider Days, which features cidermaking on an apple press that’s more than a century old. And at Green Mountain Sugar House in Ludlow, second-generation owners Ann and Doug Rose transform maple sap into sweet syrup, a process that dates back to the first European settlers—and even earlier, to the native Abenaki before them.

Foodies aren’t the only ones to benefit from the Okemo Valley’s preservation-minded character. Architecture fans marvel at Chester’s trove of rare “snecked” stone buildings, the handiwork of Scottish immigrants in the 1800s. In Grafton, dozens of early structures have been saved by the local Windham Foundation (which also buried downtown power lines for added historic authenticity). Among the foundation’s properties is a cabin at Journey’s End, the homestead of a formerly enslaved man named Alec Turner and now part of the Vermont African American Heritage Trail.

Shoppers can step back in time at The Vermont Country Store, founded in Weston in 1946, where the jingle of an old-fashioned shop bell welcomes you to a cornucopia of gadgets, gifts, foods, and brands remembered from childhood.