Wend Your Way

Hop on board for an unforgettable driving tour of the central Berkshires. On this tour, you will explore quaint Berkshire towns, memorable museums, beautiful gardens, and much more.

Begin your tour in the Town of Lenox. Charming Lenox offers unique shopping, galleries, and eateries all within easy walking distance from one another, so it’s a great spot to take an hour or two to let your group explore and get a taste of the area. For the theater buffs in your group, enjoy a detour over to the Shakespeare & Company campus just outside of downtown. After exploring Lenox, head to MA 183 south. As you drive along Route 183, you will pass Tanglewood  on the left, the legendary summer home of the Boston Symphony Orchestra. Concerts have been held at Tanglewood since 1937 and offer a vast range of musical forms and styles in addition to incredible Berkshire views and manicured grounds for exploring and picnicking. On the right after Tanglewood, you will pass the Kripalu Center for Yoga and Health, which provides nationally-recognized, year-round programs in wellness, self exploration, and yoga.  

Continue on Rt. 183 and take a slight left on Interlaken Rd./MA 183. At the intersection of 102 and 183, you will find the Berkshire Botanical Garden. Turn right on Rt. 102 for ample bus parking on the left. The Berkshire Botanical Garden encompasses over 15 acres of land and features dozens of display areas with an emphasis on plants that are native to the Northeast. This might be a great spot to add to your next garden itinerary.

After the Berkshire Botanical Garden, continue south on Rt. 183 until you reach the Norman Rockwell Museum on the left (appx. 1 minute from Berkshire Botanical Garden). The Norman Rockwell Museum houses the world’s largest and most significant collection of Rockwell art. In addition, Rockwell’s studio is open seasonally and there are beautiful, expansive grounds for strolling. After the Norman Rockwell Museum, head to Chesterwood, the country home, studio, and gardens of America’s foremost sculptor, Daniel Chester French (Lincoln Memorial). To get there, take a 2-minute drive: proceed southwest on Glendale/MA 183 toward Butler Rd., then take a right on Mohawk Lake Road. Take your first left onto Willow Street, which becomes Williamsville Road, and you will find Chesterwood at 4 Williamsville Road on the right. 

Next stop is the Hancock Shaker Village, located approximately 13.7 miles and 24 minutes away. The drive to Hancock Shaker Village is along one of the prettiest Berkshire roads, showcasing the natural scenic beauty surrounding you in all directions. To get there from Chesterwood, head east on Williamsville Road, take your first right on Christian Hill Road, then first left onto Rt. 183/Glendale Road. Follow along until you reach Route 102, then take a left. You will eventually arrive in the town of West Stockbridge, a quaint community offering delightful shops, Turn Park, and delicious eateries, like Rouge Restaurant & Bistro and Truc Orient Express. Continue to follow 102 West, turn right on 41, and drive through Richmond. The trip takes you through scenic farmland and wooded surrounds. Follow to the end and take a left onto Rt. 20.  Hancock Shaker Village is immediately on the left.

The Hancock Shaker Village operates as a living-history museum open to the public with 20 authentic Shaker buildings, rich collections of Shaker furniture and artifacts in rotating exhibits, a full schedule of activities and workshops, a mile-long hiking trail and picnic areas, store and café, and a working farm with extensive gardens and heritage-breed livestock. It’s a substantial and uniquely Berkshire experience for your group.

All three of the museums mentioned have great group packages and special tours, so be sure to hop off the bus during this drive and take in some culture. Your group is sure to enjoy the drive as they get to know the Berkshires.

Photos (top to bottom): Shakespeare & Company / Berkshire Botanical, photo: Chi Chi Ubina / Hancock Shaker Village, photo: Kara Thornton