Attractions in the Berkshires for Romantic Couples

Massachusetts' Berkshires are an Ideal Destination for Fun-Loving Couples

wheatleigh lenox palace
A lovely retreat for couples, Wheatleigh in Lenox overlooks a well-manicured lawn and gardens. Wheatleigh.

The sylvan Berkshire Mountains have for centuries lured artists and writers, millionaires and scoundrels (these were often one and the same), and romantic couples just like you in search of fun, entertainment, and a bit of culture. Graced with natural beauty, the Berkshires also boast some of the loveliest cultivated scenery in America. When a romantic couple decides to spend time here, that becomes a backdrop for days of fun and exploration. What's not to be missed? These are some top attractions in the Berkshires for a couple in love to explore.

01 of 09

The Mount: A National Historic Landmark

Symmetrical interior hallway.

Vincent Sardone

2 Plunkett St, Lenox, MA 01240, USA
Phone +1 413-551-5111

Opened in 1902, The Mount became author Edith Wharton's haven. The Gilded Age mansion was designed in accordance with the principles she espoused in The Decoration of Houses; many consider this a seminal book in the field of interior design. Not only did Wharton create a house and garden of proportion, harmony, and symmetry, she also authored some 40 books in 40 years, including The Age of Innocence and The House of Mirth.

A restoration work in progress, The Mount (entrance fee) hosts cultural events (check the website for the schedule). Have a drink and listen to live jazz summer weekend evenings on the terrace overlooking the formal gardens. The Mount is open May through October and on weekends in November and December. 2704, 2 Plunkett St, Lenox.

02 of 09

Hancock Shaker Village: A National Historic Landmark

Round barn, which enabled livestock to move even in inclement weather.

Vincent Sardone

1843 W Housatonic St, Pittsfield, MA 01201-7513, USA
Phone +1 413-443-0188

It might not seem like a couple's first choice of a place to visit for fun in the Berkshires — after all, the Shakers were a religious sect dedicated to simplicity, community, and celibacy. Their heyday extended from 1783 to 1960. Given their lack of fecundity, it's unsurprising that none are left.

Yet their good works live on, proving that you can get a lot done when your mind is on other things. At Pittsfield's 1,200-acre Hancock Shaker Village (entrance fee), learn about the group and how they lived via a short video. Adjacent galleries display the distinctive chairs, tools, and boxes their busy hands fashioned. Then stroll the grounds to see the round barn, historic buildings, and garden that are the enduring fruits of their labor. 1843 W Housatonic St, Pittsfield.

03 of 09

Norman Rockwell Museum

9 Glendale Rd, Stockbridge, MA 01262, USA
Phone +1 413-298-4100

Known as the man who illustrated covers of The Saturday Evening Post with visions of a wholesome and optimistic Americana, Norman Rockwell lived and painted in Stockbridge. This museum (entrance fee) dedicated to Rockwell was designed by architect Robert A.M. Stern and features a 15-minute biographical video that describes his life, his work, and his values. The museum's collection consists of more than 600 of Rockwell's patriotic paintings as well as his many magazine covers. Visitors can also step into an authentic recreation of Rockwell's studio. 9 Route 183, Stockbridge, 413-298-4100.

04 of 09


297 West St, Lenox, MA 01240, USA
Phone +1 413-637-5180

You don't have to love classical music to visit Tanglewood, the summer home of the Boston Symphony Orchestra. Under Tanglewood's Koussevitzky Music Shed, you can have comfortable seats protected from the elements. But romantic couples often prefer to buy cheaper general admission tickets. That way, the music serves as a serenade to their own summer picnic on the grass. 297 West St, Lenox.

Continue to 5 of 9 below.
05 of 09

Berkshire Botanical Garden

5 W Stockbridge Rd, Stockbridge, MA 01262, USA
Phone +1 413-298-3926

Take a romantic stroll through one of New England's oldest public gardens. For more than 75 years, lovers of flowers and gardening have found respite and inspiration at the Berkshire Botanical Garden (entrance fee). Among the discrete green spaces are an herb garden, rock garden, and rose garden. There are also gardens dedicated to local luminaries. And depending on when you plan to visit, the Berkshire Botanical Garden may host an event or special exhibition that particularly interests you. The facility is particularly keen on educating visitors about home-grown food. 5 West Stockbridge Road, Stockbridge, 413-298-3926.

06 of 09

Chocolate Springs Café

55 Pittsfield Rd, Lenox, MA 01240-2122, USA
Phone +1 413-637-9820

Scientists believe that the theobromine in chocolate stimulates the pleasure center in the brain. Romantic couples believe that Valentine's Day isn't the only time to break out the brown stuff. In the Berkshires at the Chocolate Springs Café, all forms of the delectable substance are available, including bars, candies, ice cream, and cocoa to drink. We chose ice cream, which was stylishly presented in lacquered Japanese bowls and served with espresso spoons. The only thing missing from our foray to this seductive site was having a private room to paint one another's body with chocolate and lick off the excess. 55 Pittsfield Road, Lenox, 413-637-9820.

07 of 09

McTeigue & McClelland Jewelers

454 Main St, Great Barrington, MA 01230-1821, USA
Phone +1 413-528-6262

If you appreciate precious stones and settings that transform them into works of enduring art, pay a visit to these Berkshire jewelers. Working with rare stones such as rubies, sapphires, emeralds, tsavorite, and white and yellow diamonds, the experienced staff marries the gems to imaginative settings. Many evoke phenomena of the natural world, others recall vintage mountings, and still others are simply graceful, elegant designs.

An individual planning to pop the question on a romantic Berkshires holiday could not go wrong choosing an engagement ring here (there's even a whimsical "cheapskate" model, which comes with a mini magnifying glass over the small diamond). 454 Main Street, Great Barrington, 800-956-2826.

08 of 09

Crane Museum of Papermaking

32 Pioneer St, Dalton, MA 01226, USA
Phone +1 413-684-6380

Anyone who's shopped offline for wedding invitations or other fine stationery has heard of the Crane brand. At this museum, which is listed on the National Register of Historic Places, visitors can trace the history of American papermaking from Revolutionary days. The museum is open on weekdays from May through August. Free admission. 32 Pioneer St, Dalton, 413-684-6380.

Continue to 9 of 9 below.
09 of 09

Rouge: A Romantic Restaurant

3 Center St, West Stockbridge, MA 01266, USA
Phone +1 413-232-4111

A favorite with locals and visitors alike, Rouge is a cozy and romantic French bistro in the Berkshires. Diners have a choice of eating at the bar or a table. The New York-trained chef/owner and his wife turn out sophisticated and seductive fare for appreciative guests. Oysters, prix-fixe meals, and desserts are particularly popular. 3 Center Street, West Stockbridge, 413-232-4111.

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Romantic Attractions and Activities in the Berkshires for Couples