The One Massachusetts Town Everyone Should Visit At Least Once

In the quaint New England town of Stockbridge, its ties to famed artist Norman Rockwell make it a memorable place to visit, but this small town nestled in the heart of Massachusetts has proven to be a literary haven for other writers, artists, and musicians as well. Although Rockwell may be the most well-known, he is certainly not the last artist who will leave their mark on Stockbridge. Visit legendary homes, museums, and monuments dedicated to the cherished celebrities of this one Massachusetts town, which everyone should visit at least once.

Artists and Their Accolades

One of the most prolific artists of his generation is memorialized in Stockbridge, his home for the last 25 years of his life, at the Norman Rockwell Museum. Within the 36-acre campus, all 323 of Rockwell’s The Saturday Evening Post covers are on display, as well as special exhibits that highlight works of leading illustrators from the past and present. Exhibits in the museum are constantly rotating, and have included works titled Norman Rockwell: Home for the Holidays, Jazz Age Illustration, All for Laughs: The Artists of the Famous Cartoonists Course, and more. Enjoy all the museum has to offer, including 998 original works of art by Rockwell and a visit to his studio, which features original art materials, his library, furnishings, and personal items. Rockwell left such an imprint on the picturesque town that every year it celebrates one of his most famous paintings at the Stockbridge Main Street at Christmas Festival. Twinkling lights and holiday wreaths adorn the streets, bringing them to life and promoting the spirit of the holiday season. A reenactment that embodies the spirit of Rockwell’s infamous holiday scene, “Home for Christmas”, is presented, Santa greets visitors, live performances are showcased, and historic homes are opened up to tours during the annual Christmas fest.

Another cherished artist who hails from Stockbridge is Daniel Chester French, whose most prolific work includes Abraham Lincoln’s seated statue in the Lincoln Memorial. Creating over 100 statues, many of them in his studio, Chesterwood, French leaves behind a legacy for budding artists and interested parties to visit. The former summer home, studio, and garden of America’s most distinguished sculptor of public monuments is open to the public and displays French’s plaster sketches.

Historic Homes

Settled in 1734 by British missionaries, Stockbridge holds to its roots and history as far as culture and architecture go. Don’t miss a chance to view these historic houses and learn more about their origin and significance. One such house is Naumkeag. Reminiscent of the Gilded Age, this elegant garden and rare Berkshire cottage-style home was constructed on 48 acres for a prominent New York attorney and U.S. Ambassador to Great Britain, and his family. The 44-room shingle-style home remained in the Choate family from its construction in 1884 until 1958, when it was bequeathed to The Trustees. Continue your learning tour of the citizens who came before at The Mission House. The Colonial-era home and garden have been converted into a museum that tells the story of the Stockbridge Mohicans and missionary John Sergeant. Built by missionary John Sergeant himself, the house stood watch over Stockbridge for nearly 200 years. Sergeant settled in Stockbridge in 1734 to assimilate the Mohican people, and the house was built for him and his family to continue their defense of the Mohicans.

The Merwin House is a late Federal-style home with a Shingle Style wing wrapped around the back of the house overlooking the Housatonic River. It is also located in the heart of the Berkshires and contains the Doanes family’s European and American furnishings and objects collected from their travels.

Delicious Dining

Mix vintage and dining at the 1980-constructed building that houses Michaels Restaurant. The menu might slightly change and update due to accommodating trends, but the good food and quick service still remain. Michaels has prided itself on their warm and welcoming atmosphere that encourages patrons to continue coming back. Visit this favorable place for people to meet and enjoy Spaghetti & Mama’s Meatballs, a SteakBurger Deluxe, or Cajun Seafood Alfredo in the company of good company and friendly staff.

For a fine dining experience that also supports local farmers and small businesses, enjoy a dinner at Once Upon a Table. The menu is created on seasonal ingredients, which means it changes often, so if you find something on the menu you want to order, don’t save it for your next visit, or it could be out of rotation! Pay a visit to this historic building, and savor delicious meals at the peak of freshness.

Nearby Towns

For a nearby trip out of Stockbridge, head to Pittsfield to view another historic home. Herman Melville’s Arrowhead commemorates the author who lived and worked there while writing two of his most famous novels, Typee and Omoo. Collections in the museum include maps, photographs, diaries, business records, town and village records, and the Burleigh panoramic views, while the Attic Museum contains tools, materials, and products of the community's 19th-century brush and oilcloth industries. Explore the house and continue outside for more exploration at Pittsfield State Forest. The 11,000-acre forest includes 30 miles of trails for hiking, mountain biking, horseback riding, or exploring the mountain range. Get in some miles before relaxing at the local Berry Pond.

Just down the road, the small town of Lenox is home to even more dated homes with stories to tell. The Mount, built by Edith Wharton in 1902, is more than just a significant home; it's also a cultural center and public park. Ever-changing exhibits are on display in the museum, including The Hoppin Albums: Building The Mount, Treasures of the Library, and The Garden of My Soul: Edith Wharton in France. Ventfort Hall, a Gilded Age Mansion and Museum, also invites visitors to take a peek at life throughout different generations. The Berkshire Cottage, constructed in 1893, is notoriously haunted and offers ghost tours and paranormal investigations led by expert guides.

Spend some time outdoors in Lee, at the October Mountain State Forest. The largest state forest in Massachusetts offers a variety of activities, including hiking, fishing, camping, mountain biking, canoeing, and more. Opt for the outdoors and get some fresh air across the 16,500 acres of park. After a relaxing hike, or vigorous, depending on your level of activity, enjoy a fine meal at 51 Park Restaurant & Tavern. Offering a fresh spin on classic tavern fare, this restaurant crafts its menu items from scratch using high-quality, fresh ingredients. Try the turkey pot pie, steak tips, or baked mac and cheese, and be sure to wash it down with a signature cocktail.

Where Art, History, and Legacy Meet

For fans of architecture, furnishings, history, and art, Stockbridge has found a way to combine all those elements into their offered attractions. The town and historic societies have converted houses into museums, preserving the original design and as much of the house and decorations as possible, so visitors can experience what life was like in the past. Explore these homes and so much more in this one Massachusetts town everyone should visit at least once.