Paddle around in Littleville Lake in Chester and Huntington, hike in Chester-Blandford State Forest, its rock steps built by the Civilian Conservation Corps, or admire the steeple on First Congregational Church in Lee, said to be the tallest steeple in the country.
The Huntington Country Store, a warren of rooms full of everything; Lee has preserved its 19th-century architecture.
photos by bill regan for the boston globe

BECKET — Beside Route 20 in Becket, a funky cairn of jumbled stones stands on the crest of a hill, capped with a granite block inscribed “1910.” That year, on Sept. 24, officials and motorists piled the stones here to celebrate the opening of the Jacob’s Ladder Trail and mark its highest spot. At the time, this “auto trail” was the nation’s first highway built to convey “horseless carriages” over a mountain range, or so its promoters claimed. Hailed as “the first of the great mountain crossovers,” the road’s official name alluded to a biblical story, Jacob’s dream of angels climbing and descending a stairway to heaven. This all seems grandiose today, considering that the road’s highest elevation — 1,775 feet — measures only thigh-high to the tallest of the White Mountains. But auto trails were designed to promote automobile tourism.

From the cairn, not much in the way of settlement or commerce interrupted the view of rolling woods and pastures in 1910. And that was the point: Taking a long car ride into the wilds of the southern Berkshires was a grand adventure.

Today, that sense of a bygone rural America still prevails along what is now called the Jacob’s Ladder Trail Scenic Byway — a 35-mile stretch of Route 20 that winds through Russell, Huntington, Chester, and Becket before ending in downtown Lee. These towns have their own charms, although, with the exception of Lee, little in the way of tourist commerce — or traffic. The chief attractions are the glimpses of country life, views of the mountains and rivers, and convenient access to lesser-known state forests and parks.

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Russell marks the route’s eastern end, just a few miles from Westfield, where the Westfield River first tumbles into view, beginning a dance with Route 20 that continues during the first half of the drive. In higher water, anglers cast for trout in its riffles, and paddlers dig into the whitewater at the annual spring canoe race in Russell and Huntington. Hydro dams along the Westfield create deep pools that mirror the overhanging trees. One can be seen on Woronoco Road in Russell, which dips to a steel bridge near a dam where the canoe race ends.

Just over the Huntington line, a small park reveals more glimpses of the river. In the spirit of the original auto trail, tables and a gazebo invite an old-fashioned roadside picnic. (Beware: Poison ivy crowds the trails along the water.) Shortly afterward, Route 112 splits off to the Huntington Country Store, which houses a warren of creaky-floored rooms packed with everything from apple turnovers to Darth Vader Christmas ornaments.

Farther down Route 112, Littleville Road leads to Littleville Lake, a dammed stretch of the Westfield’s middle branch that is open for boating and fishing. The dams on each end offer perches for long views of calm water. Route 112 also provides access to Huntington State Forest, Gardner State Park, and Chester Wildlife Management Area, all off the beaten track.

Back on Route 20, the Chester-Blandford State Forest beckons with a roadside entrance, including a handicap-accessible trail to a part of the forest called Boulder Park. This little cul-de-sac looks out on a spill of boulders, one as large as a tractor-trailer, dropped by the last glacier. In the 1930s, when the Civilian Conservation Corps built this park, people were content to sit and marvel at these natural wonders. Now the CCC’s enduring stonework and wood picnic shelters seem nearly as marvelous.

Chester Center once was a busy depot for the Boston and Albany Railroad, which still passes through. The most fascinating remnants of the railroad heyday stand outside of town: the massive Keystone Arch Bridges, built between 1833 and 1841, which can be reached only on foot. Made of unmortared stone, these massive arches frame spectacular views of water and forest. Trail parking lies off Middlefield Road, which peels off from Route 20 in Chester Center.

Jacob’s Ladder Trail meanders through Becket State Forest as it climbs to the cairn, then passes the entrance to Jacob’s Pillow Dance Festival (closed for the season) before skirting the edge of the vast (16,500-acre) October Mountain State Forest in Lee, which contains a section of the Appalachian Trail. Lee, the gateway to the Berkshires’ cultural realm, remains a tidy working city with a splendid 19th-century Main Street. Anchoring the common, the First Congregational Church pierces the sky with a blindingly white wooden steeple that is allegedly the nation’s tallest. And for anyone whose cash has been burning a hole in their pockets during the ride, the Lee Premium Outlets should satisfy the craving.