Reminder of a simpler time

Take a drive across “the first of the great mountain crossovers” and feel transported back to a slower, simpler era. The Jacob’s Ladder Trail Scenic Byway traverses unspoiled and historic rural landscapes, anchored by Tekoa Mountain in the east and Laurel Lake in the west.

Auto tourism’s heyday

On a rainy day in 1910, as many as 4,000 people gathered at the summit of Morey Hill in Becket to mark the completion of the country’s first auto road over a mountain range. The crowd built a stone cairn at the 1,775-foot summit, which remains an icon. While other parts of the state have experienced a population boom over the past few decades, the Jacob’s Ladder Trail has retained its rural feel. Today’s travelers will pass many of the same vistas and sites that greeted motorists in the 1910s and ’20s.

Miles of hiking and skiing

Natural wonders and year-round outdoor recreation options are plentiful. Chester-Blandford State Forest contains two of the region’s most scenic waterfalls, Sanderson Brook and Goldmine Brook. October Mountain State Forest in Lee is the largest state forest in Massachusetts, with 16,500 acres of wild terrain for camping, hiking, mountain biking, snowshoeing, hunting, off-roading and snowmobiling. You’ll find parking and trailheads for the Appalachian Trail in Lee. Cross-country skiers won’t want to miss Canterbury Farms in Becket. Its 12 miles of trails were designed and groomed specifically for cross-country skiing and ski-skating, and equipment rentals are available. Blandford Ski Area offers day and night downhill skiing and a terrain park.

Rollin’ on the rivers

The nationally designated Wild and Scenic Westfield River is a prime canoeing, kayaking and tubing destination when the water level is high with snowmelt or rainfall. In April, spectators can watch the expert Westfield River Whitewater Races from locations in Huntington and Russell. If you want a gentler ride, the Housatonic River offers a meandering trip through fields, floodplain forests and open water. You’ll find boat launches in Lenox and Lenox Dale, just north of Lee. Look for bald eagles and herons in shoreline trees, and turtles basking on the riverbanks.

Westfield River Whitewater Races PHOTO: JEFF PENN


Railroad enthusiasts of all ages will want to seek out the Keystone Arches, stone railroad bridges in Middlefield, Becket and Chester, built around 1840. Built without mortar or steel reinforcements, they’re testaments to the engineering feats of the period and were the first bridges of their kind in the country. A 2.5-mile trail with plenty of spurs offers a chance to see the bridges up close and document active trains. The Railroad Depot and Museum in Chester houses historic exhibits and restored railroad cars of the 1910s and ’20s. The museum also hosts the Chester on Track railroad festival each May.

World-renowned dance performances

Each summer, the Carter Farm in Becket is transformed into one of the world’s premier dance festivals and workshops—the Jacob’s Pillow Dance Festival. Known simply as The Pillow, the festival welcomes thousands of visitors with free performances and family-friendly programs and hosts more than 50 internationally renowned dance companies from North America and Europe, as well as Brazil, India and Israel. The Chester Theatre Company and Vincent Dowling Theater Company offer first run world class performances in intimate settings. North Hall in Huntington presents a Summer Arts series that includes opera and theater performances.

Constructed in 1981 to provide additional rehearsal space, this outdoor stage is set against a stunning Berkshire Hills backdrop and is known as the Marcia and Seymour Simon Performance Space or Inside/Out. Erica Essner Performance Co-Op performing as part of the Inside/Out performance series, 2007 BY CHRISTOPHER DUGGAN. COURTESY OF JACOB'S PILLOW DANCE

Gateway to the berkshires

Thousands of visitors pass through the town of Lee on their way to the cultural venues and scenic beauty of Berkshire County. Main Street in Lee is lined with shops and restaurants in landmark Victorian buildings. A public boat ramp on the Lee–Lenox border offers access to Laurel Lake, a popular spot for boating and year-round fishing.

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