Romantic Getaways: Top Berkshires Attractions for Couples

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, it becomes a backdrop for days of fun and exploration. So, what’s not to be missed? Here are some top attractions in the Berkshires that couples can explore together.

The Mount: A National Historic Landmark

Address: 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 work in the field of interior design. Not only did Wharton create a house and garden of proportion, harmony, and symmetry, but she also authored approximately 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. Couples can enjoy drinks and live jazz on summer weekend evenings on the terrace overlooking the beautiful formal gardens. The Mount is open May through October and on weekends in November and December.

Hancock Shaker Village: A National Historic Landmark

Address: 1843 W Housatonic St, Pittsfield, MA 01201-7513, USA

Phone: +1 413-443-0188

While Hancock Shaker Village may not initially seem like an obvious choice for a couple’s adventure, this historic site offers rich insights into a unique lifestyle dedicated to simplicity and community. At Pittsfield’s 1,200-acre Hancock Shaker Village (entrance fee), visitors can learn about the Shakers through a short documentary. They can then explore adjacent galleries showcasing distinctive creations like chairs, tools, and boxes made by the Shakers. Couples can also stroll the lovely grounds to discover the round barn and garden—the enduring fruits of Shaker labor.

Norman Rockwell Museum

Address: 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 wholesome and optimistic Americana, Norman Rockwell lived and painted in Stockbridge. This museum (entrance fee) dedicated to Rockwell features a captivating biographical video that describes his life, work, and values. With more than 600 paintings, including patriotic works and magazine covers, the museum encapsulates Rockwell’s poignant perspective on American life. Visitors can also explore a carefully recreated version of Rockwell’s studio.

Tanglewood

Address: 297 West St, Lenox, MA 01240, USA

Phone: +1 413-637-5180

Tanglewood, the summer home of the Boston Symphony Orchestra, opens its doors to everyone, regardless of their love for classical music. Under the Koussevitzky Music Shed’s shelter, couples can enjoy comfortable seating while listening to enchanting performances. Alternatively, many couples opt for general admission tickets to savor their romantic summer picnic on the grass, with music as a beautiful backdrop.

Berkshire Botanical Garden

Address: 5 W Stockbridge Rd, Stockbridge, MA 01262, USA

Phone: +1 413-298-3926

Couples will appreciate a romantic stroll through one of New England’s oldest public gardens. For over 75 years, enthusiasts of gardening and flowers have found inspiration and tranquility at the Berkshire Botanical Garden (entrance fee). Guests can explore varied landscapes, including an herb garden, rock garden, and rose garden, as well as special events and exhibitions that may align with their visit.

Chocolate Springs Café

Address: 55 Pittsfield Rd, Lenox, MA 01240-2122, USA

Phone: +1 413-637-9820

Scientists assert that theobromine in chocolate stimulates the brain’s pleasure center, making it a favorite for couples who appreciate sweet indulgences. At Chocolate Springs Café, lovers can enjoy a delightful selection of chocolate bars, candies, ice cream, and rich cocoa. The stylish dessert presentations make this spot a true treat for romantic outings.

McTeigue & McClelland Jewelers

Couples with an appreciation for exquisite jewelry should visit these esteemed Berkshire jewelers. The skilled team specializes in rare gems—including rubies, sapphires, emeralds, and diamonds—crafted into imaginative settings. For anyone considering an engagement, this destination offers stunning options, ensuring that any ring chosen will be a cherished symbol of love.

Crane Museum of Papermaking

Address: 32 Pioneer St, Dalton, MA 01226, USA

Phone: +1 413-730-5055

Art lovers and stationery enthusiasts alike will find the Crane Museum intriguing. Recognized on the National Register of Historic Places, the museum tells the story of American papermaking, revealing its evolution since Revolutionary times. Open weekdays from May through August, this unique destination offers free admission for all.

Rouge: A Romantic Restaurant

Address: 3 Center St, West Stockbridge, MA 01266, USA

Phone: +1 413-232-4111

Beloved by locals and visitors, Rouge is a cozy French bistro where couples can indulge in sophisticated fare. The talented chef creates exquisite dishes—including oysters and prix-fixe meals—that delight the palate, making this an ideal venue for a romantic dinner experience.