5 things to do when visiting Stockbridge

Walk a twinkling historic property, go hiking, and step into a Norman Rockwell painting.

Main Street at Christmas in Stockbridge. Stockbridge Chamber of Commerce

Stockbridge is a western Massachusetts town full of culture and nature that’s nationally renowned for its Christmas spirit, said Carole Owens, a resident for 50 years.

“It is really the quintessential New England village,” said Owens, a retired doctor, author, and editor of stockbridgeupdates.com.

American painter and illustrator Norman Rockwell famously lived and worked in Stockbridge during the final 25 years of his life.

“A lot of people think that Norman made Stockbridge famous, but the thing is that Stockbridge inspired Norman,” Owens said. “In all those elements that you look for in Christmas — the neighborliness, the generosity, the warmth, the old fashioned beauty — all that is still in Stockbridge and that’s what makes it a village that symbolizes Christmas.”

Owens shared her picks for what to see and do when visiting Stockbridge.

1. Step into a Norman Rockwell painting

Every December, Stockbridge re-creates Norman Rockwell’s 1967 painting “Stockbridge Main Street at Christmas (Home for Christmas)” during the annual Stockbridge Main Street at Christmas festival full of holiday markets, live performances, historic property tours, horse-drawn carriage rides, and more. This year’s festival takes place Dec. 1-3.

Rockwell completed the oil-on-canvas painting in 1967 for publication in McCall’s magazine. The painting “has come to symbolize Christmas in America,” wrote the Norman Rockwell Museum. Owens was present at the very first Stockbridge Main Street at Christmas, which is now in its 34th year.

Organizers close the portion of Main Street that’s in the painting to traffic and recreate it with details such as strategically placed vintage cars and a Christmas tree in the window above the Stockbridge General Store, which was Rockwell’s studio from 1953 to 1957.

Owens said her favorite part of the weekend is the Caroling Luminaria Walk, where carolers walk with candles from The Red Lion Inn to the First Congregational Church.

“It’s just beautiful,” she said.

The Red Lion Inn in Stockbridge. *– Red Lion Inn*

2. Dine on Main Street

Speaking of Stockbridge’s Main Street, it’s a great place for dining, Owens said.

It’s well worth spending time at The Red Lion Inn, featured in Rockwell’s painting and “almost a destination in itself,” Owens said.

The property features four different dining experiences: the historic Main Dining Room with crystal chandeliers, antique china, classic New England entrees, and an extensive wine list; Widow Bingham’s Tavern, a family-friendly tavern named after one of the inn’s original owners; The Courtyard, where diners relax outside during warm weather; and The Lion’s Den, a historic speakeasy. Winter hours vary at the restaurants, so visitors should check the website before visiting.

Elsewhere on Main Street are “some fun surprises” in the way of dining, Owens said.

Main Street Cafe is a “wonderful” breakfast and lunch spot, she said. She called The Lost Lamb “a first-rate bakery,” and Once Upon a Table is a farm-to-table restaurant that’s “quite eclectic and pretty surprising,” Owens said.

3. Attend the theater, a concert

Stockbridge shines when it comes to theaters and concerts, Owens said.

Theater-goers can check out “A Christmas Carol” this holiday season at The Unicorn Theater, part of The Berkshire Theatre Group. Sensory-friendly performances are available for the show. The Berkshire Theater Group has two theaters in Stockbridge, and the other is The Fitzpatrick Main Stage.

Tanglewood, situated on 500 acres, is a renowned Berkshires venue and summer home of the Boston Symphony Orchestra. Tanglewood welcomes more than 350,000 visitors each summer. Performances are held at the open-air Koussevitzky Music Shed, Seiji Ozawa Hall, and the Linde Center for Music and Learning.

“It’s a culture in the country experience,” Owens said. “It’s nature and culture. So you are outside in a beautiful space, relatively undeveloped, and you are there to hear music and it could be classical, it could be pop, it could be full orchestra, it could be a quartet, it could be a duet. It’s a wonderful experience.”

View thousands of winter lights at Naumkeag in Stockbridge. – The Trustees of Reservations

4. Visit a museum, historic property

Stockbridge boasts excellent museums and historic properties, Owens said.

The 48-acre Naumkeag, a public garden and historic home built in 1886 by New York attorney Joseph Choate, shimmers with thousands of lights every holiday season during Winterlights.

The Norman Rockwell Museum, located on a scenic 36-acre campus, offers 10 galleries showcasing the work of Rockwell and other leading illustrators. Visitors can currently check out “Norman Rockwell: Winter Wonderland,” featuring Rockwell’s connection to holiday-inspired art, which opened in November and runs through Feb. 25, 2024.

“It’s fabulous,” Owens said about the museum. “They include things that are very popular like Marvel comic books and they look at the whole scope of illustration, but always with the focus on Norman Rockwell,” Owens said.

The Mission House is a Colonial-era house, museum, and garden where visitors can learn about the Stockbridge Mohicans and missionary John Sergeant. The house is currently closed for the season, but the garden is open daily.

The 24-acre Berkshire Botanical Garden, established in 1934 and billed as “one of the older public display gardens in the Northeast,” will feature a Holiday Marketplace Dec. 9-10.

5. Go on a hike

Stockbridge has great hiking trails for all skill levels, Owens said.

Hikers will find trails at the 95-acre Gould Meadows and the 42-acre Bullard Woods.

The Laurel Hill Association of Stockbridge, the oldest village improvement society in the U.S., maintains more than 460 acres with trails. Owens recommends a trail named after her good friend Mary Flynn, a longtime teacher and public servant in town.

The Mary V. Flynn Trail is a 1.2-mile loop along the Housatonic River that is “easy and lovely,” Owens said. Another trail, Laura’s Tower Trail, is a 1.5-mile moderately difficult mountainous climb to a summit tower with panoramic views of the Berkshires. And the Ice Glen Trail is a difficult 1-mile hike in a glacial ravine.

“Ice Glenn is a geological phenomenon,” Owens said. “It is not an easy trail. There’s a bit of scrambling up and down rocks. This is a serious walk but absolutely gorgeous and unforgettable.”