Total distance: 25 miles. See more at The Berkshires.org
A day of leisurely driving, poking in antique and gift shops, and watching beautiful small towns float past can start in Sheffield on Route 7 in the southwestern corner of the Berkshires. Of the scores of antique shops in the region, Sheffield has Cupboards & Roses Swedish Antiques, Painted Porch Antiques, Susan Silver Antiques, and many more. Berkshire County Massachusetts Antiques and Art Dealers.
-- Take Route 7 north for 6.5 miles to…
As in Sheffield, antique shops are easy to find in Great Barrington. Other shopping adventures include interesting gift shops, like Michael Wainwright, which makes hand-made tableware and gifts.
Any child in your life will appreciate your stopping at Tom's Toys, offering popular and unique playthings, and at Robin's Candy Shop, selling old-time candy and nostalgic treats.
People interested in American history can explore the African American Heritage Trail, 48 sites celebrate Black luminaries – W.E.B. DuBois, Rev. Harrison, Elizabeth Freeman and ordinary African Americans, and the W.E.B. Du Bois Center, and the home site of this hero of American liberty.
Asia-Barong shows museum-quality art, furniture and sculpture. Finally, take a peek at the Mahaiwe Performing Arts Center, a restored historic theater.
-- Continue north on Route 7 for 8 miles to…
Attractions include the year-round Berkshire Botanical Garden, featuring 23 seasonal display gardens, classes, and exhibits. Chesterwood is the country home, studio, and gardens of Daniel Chester French, the admired sculptor who created of Abraham Lincoln for the Lincoln Memorial and many other works. Naumkeag House and Gardens is a 19th-century summer country estate where visitors can enjoy the gracious house, magnificent gardens, and panoramic views.
The popular Norman Rockwell Museum shows exhibits of work by the beloved illustrator, along with a stream of changing exhibits and special events. The Schantz Galleries exhibit glass art by Dale Chihuly, Lino Tagliapietra & William Morris. Another jewel for art lovers is Sohn Fine Art, offering contemporary art and specializing in photography.
Fun shopping in Lenox is at Williams & Sons Country Store and Charles H. Baldwin & Sons, two delightful, old-fashioned country stores; Hotchkiss Mobiles Gallery, with jewelry, glass & outdoor sculpture; and the popular Yankee Candle Company.
-- Continue north on Route 7 for 7 miles to…
This is the home of Tanglewood, where the Boston Symphony and its many world-caliber guests perform classical, popular, and jazz concerts June to Labor Day. Get tickets if you can or if you visit in the off season it is nice just to walk the grounds.
In the realm of performing arts, Shakespeare & Company presents old and new drama and comedy from May to March, including shows for kids at two theaters on this grassy, park-like property. Visitors are welcome to picnic on the grounds.
J. P. Morgan, build his kid sister a mansion in 1893, now called Ventfort Hall Mansion. Visitors can tour the grand estate and its art gallery or simply enjoy the architecture. Another historic Lenox place is The Mount, the 1902 home of 19th-century socialite, garden designer, and author Edith Wharton. Also, Frelinghuysen Morris House & Studio is the International-style home of American abstract artists set on 46-acre estate, offering guided tours of Cubist masterpieces.
Still have a yen to shop? You can manage that at a variety of unique places, including Berkshire Classic Leather & Silver (jackets, handbags, jewelry), and Colorful Stitches, called the "most inspirational yarn store in the nation.”
-- Take Route 20 northbound for about 7 miles to…
Visit the Berkshire Museum to enjoy a fantasy-like collision of art, history, and science. Enjoy the museum's aquarium, dinosaur dig, classic and modern art and more. Another way to get really close to history is with a stop at Hancock Shaker Village. From April to October, this authentic Shaker community welcomes visitors to enjoy its historic buildings, craft demonstrations, gardens, exhibitions and special events. There's great shopping and dining here, too.
For shopping fun, the intriguing Museum Facsimiles Factory Outlet Store welcomes browsers among the ornate frames and framed mirrors, letterpress cards, vintage posters, stationery, and more.