A Day Trip to the Berkshires: Art, History & Village Charm

Intro

Travel north through the scenic Litchfield Hills for an unforgettable day in the Berkshires, where American art, Gilded Age grandeur, and charming New England shopping await.

Our first stop is the historic village of Stockbridge—the New England setting that inspired Norman Rockwell and appeared in many of his most beloved works. Enjoy a picturesque drive through town, passing Rockwell’s former home on South Street and his Main Street studio, the historic Old Corner House.

Then, explore the Norman Rockwell Museum, home to an extraordinary collection celebrating one of America’s most cherished artists. View full-size original paintings, along with all 323 covers he created for The Saturday Evening Post. Special exhibitions add even more inspiration, spotlighting the artistry, impact, and imagination of influential illustrators from past and present.

In the early afternoon, we arrive in Lenox for the day’s highlight: an unforgettable visit to Ventfort Hall Mansion & Gilded Age Museum. Begin with lunch in an elegant dining room once enjoyed by Gilded Age socialites, then step back in time on a guided tour of this magnificent estate.

Built in 1893 for Sarah Morgan, sister of financier J. P. Morgan, this imposing Jacobean Revival–style mansion was designed by the acclaimed architectural firm Rotch & Tilden. Listed on the National Register of Historic Places and recognized as an official Save America’s Treasures project, Ventfort Hall is now home to the Museum of the Gilded Age.

One of approximately 75 grand “cottages” built in Lenox during its late-19th-century heyday as a fashionable resort destination, the mansion stands on spacious grounds in the heart of the village. Visitors will explore the fully restored first floor and select second-floor rooms, each offering a glimpse into an era of extraordinary wealth, style, and influence.

Through engaging exhibits and beautifully preserved interiors, the museum brings to life the social, industrial, and cultural transformations that shaped 19th-century America.

Our final stop is Great Barrington, where you will have free time to explore this lively, artsy Berkshire town. Browse an eclectic collection of independent boutiques, contemporary clothing stores, vintage shops, gourmet food purveyors, and art galleries along its bustling main street and charming side streets.

After a day filled with art, architecture, history, and shopping, we return home with lasting memories of the beautiful Berkshires.

| 8:30 a.m. | Depart Connecticut |
| 10:00 a.m. | Arrive at the Norman Rockwell Museum
| 12 noon |  Arrive at Ventfort Hall 

| 2:30 |  Great Barrington

| 4 p.m. |  Head for Home