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1. Church on the Hill, UCC
Address: 55 Main St, Lenox.
This is a historic church building at 169 Main Street in Lenox, Massachusetts. Built-in 1805, it is one of a small number of surviving Federal period churches in the region.
2. The Mount, Edith Wharton's Home
Address: 2 Plunkett St #2704, Lenox.
This cultural center was a previous home of noted American author Edith Wharton, who designed the house and its grounds and considered it her first real home.
3. Mass Audubon's Pleasant Valley Wildlife Sanctuary
Address: 472 W Mountain Rd, Lenox.
This is a large wildlife sanctuary with unlimited natural beauty and visitors can enjoy plenty of nature trails.
4. Kennedy Park
Address: 275 Main St, Lenox.
This is a beautiful nature park with unlimited natural beauty.
5. Ventfort Hall Mansion and Gilded Age Museum
Address: 104 Walker St, Lenox.
This is a historic, Jacobean-style mansion and museum in Lenox.
6. Frelinghuysen Morris House & Studio
Address: 92 Hawthorne St, Lenox.
This museum was the house and studio were home to American Abstract Artists George L.K. Morris and Suzy Frelinghuysen.
7. Olivia's Overlook
Address: Yokun Ridge South, Hiking Trails, West Stockbridge.
This is a popular natural attraction in Lenox situated at the center of the 734-acre Yokun Ridge reserve in the heart of central Berkshire County and famous for nature trails.
8. Arrowhead Museum
Address: 780 Holmes Rd, Pittsfield.
This museum was the home of American author Herman Melville during his most productive years, 1850–1863.
9. Bousquet Ski Area
Address: 101 Dan Fox Dr, Pittsfield.
This ski area attracts visitors with skiing, snowboarding, tubing, a snow terrain park, a great learning bunny hill with a magic carpet, etc.
10. Hancock Shaker Village
Address: 1843 W Housatonic St, Pittsfield.
This is a favorite destination for children with various events and exhibitions.
11. October Mountain State Forest
Address: 317 Woodland Rd, Lee.
This is a 16,460-acre forest and recreational preserve located primarily in the town of Washington with adjoining parcels in Becket, Lee, and Lenox.
12. Balderdash Cellars
Address: 81 State Rd, Richmond.
This winery produces ultra-premium wines.
13. The National Shrine of THE DIVINE MERCY in Stockbridge - Massachussets - USA
Address: 2 Prospect Hill Rd, Stockbridge.
Roman Catholic shrine on 350 acres with a white marble Mary statue, ornate mural & Sunday Mass
14. Berkshire Museum
Address: 39 South St, Pittsfield.
This museum houses amazing collection of art, natural history and ancient civilization that is located in Pittsfield, Berkshire County, Massachusetts.
15. Naumkeag
Address: 5 Prospect Hill Rd, Stockbridge.
Visitors can tour this spacious, 19th-century summer home & picnic on its landscaped grounds.
16. Berkshire Botanical Garden
Address: 5 West Stockbridge Road, Stockbridge.
This botanical garden spreads around 15 acres and contains over 3,000 species and varieties, with an emphasis on plants that thrive in the Berkshires.
17. Tanglewood
Address: 297 West St, Lenox.
This is a popular live music venue in Lenox and it has been the summer home of the Boston Symphony Orchestra since 1937.
18. Schantz Galleries Contemporary Glass
Address: 3 Elm St, Stockbridge.
This art center houses excellent glassworks of artists.
19. Norman Rockwell Museum
Address: 9 Glendale Rd, Stockbridge.
This museum houses the world's largest collection of original Norman Rockwell art as the best of American illustration.
20. Mass Audubon Canoe Meadows Wildlife Sanctuary
Address: 309 Holmes Rd, Pittsfield.
Canoe Meadows brings wilderness to Berkshire County’s largest city, attracting warblers, turtles, ospreys, otters, and the occasional bear at different times of the year.
21. Animagic Museum of Animation
Address: 135 Main St, Lee.
This museum is dedicated to animation, special effects & art, with guided tours.