Downtown Stockbridge

Nestled in the heart of the Berkshire Mountains of Western Massachusetts, Stockbridge is a charming and picturesque town that has become a popular destination for visitors seeking a taste of New England charm and culture. From its quaint downtown area to its rich history and scenic beauty, there are many things to do and see in Stockbridge, MA.

1. Norman Rockwell Museum

One of the must-see attractions in Stockbridge is the Norman Rockwell Museum, which is located just a few miles outside of downtown. The museum is dedicated to the life and work of Norman Rockwell, one of America’s most beloved artists, who lived in Stockbridge for the last 25 years of his life. The museum houses the world’s largest collection of original Norman Rockwell art, including paintings, illustrations, and other works. Visitors can learn about Rockwell’s life and career through interactive exhibits and multimedia presentations, and even try their hand at drawing and painting in the museum’s art studio. The museum also features rotating exhibits of contemporary illustration and art.

2. Berkshire Botanical Garden

Just a few miles outside of downtown Stockbridge, the Berkshire Botanical Garden is a hidden gem that is well worth a visit. The garden features 15 acres of landscaped gardens, including a perennial garden, a vegetable garden, a rock garden, and a woodland garden. Visitors can take guided tours of the gardens, attend gardening workshops and lectures, and shop for plants and garden accessories in the garden’s gift shop. One of the highlights of the Berkshire Botanical Garden is the Center House, a beautiful Victorian-style greenhouse that houses a collection of tropical plants, including orchids and ferns. The greenhouse is open year-round and provides a welcome respite from the cold Berkshire winters.

3. Red Lion Inn

One of the main draws of downtown Stockbridge is its charming, New England-style downtown area, which is lined with historic buildings, boutique shops, and charming cafes and restaurants. At the heart of the downtown area is the Red Lion Inn, a historic hotel and restaurant that has been serving guests since 1773. The inn’s cozy pub is a popular spot for locals and visitors alike, and the restaurant serves up delicious New England fare made with locally-sourced ingredients. Don’t miss the Sunday brunch, which features an array of fresh-baked pastries, seasonal fruits, and hearty breakfast dishes.

4. Stockbridge Library

The Stockbridge Library is a community treasure, housed in a beautiful historic building in the heart of downtown. The library’s collection includes over 50,000 books, as well as a large collection of art and historical artifacts. Visitors can attend author talks and other cultural events, as well as browse the library’s extensive collection of local history resources. One of the highlights of the library is the Bement Room, a beautiful reading room with a fireplace and comfortable chairs. The room is a popular spot for visitors to relax and read a book or magazine.

5. Mahaiwe Performing Arts Center

The Mahaiwe Performing Arts Center is a beautifully restored historic theater located in downtown Stockbridge. The theater hosts a wide variety of performances throughout the year, including concerts, plays, dance performances, and films. Don’t miss the annual Berkshire International Film Festival, which takes place at the Mahaiwe each summer.

6. Laura’s Tower Trail

For outdoor enthusiasts, the Laura’s Tower Trail is a must-see attraction in Stockbridge. The trail is a moderate 2.5-mile hike that leads to the top of a hill, where visitors can climb the tower and take in stunning panoramic views of the surrounding mountains and countryside.

7. Chesterwood

Chesterwood is a National Trust historic site that was once the summer home and studio of sculptor Daniel Chester French, who is best known for his statue of Abraham Lincoln in the Lincoln Memorial in Washington, D.C. Visitors to Chesterwood can explore the sculptor’s studio and gardens, and learn about his life and work through guided tours and exhibits.

8. Naumkeag

Naumkeag is another must-see historic site in Stockbridge. The property was once the summer home of New York lawyer and ambassador Joseph Choate and his wife, Caroline. The house and gardens were designed in the Gilded Age style, and feature beautifully landscaped gardens, a picturesque pond, and a stunning view of the Berkshires. Visitors can take guided tours of the house and gardens, and learn about the Choate family’s life and legacy in Stockbridge.

9. Stockbridge Bowl

The Stockbridge Bowl is a scenic lake located just a few miles outside of downtown Stockbridge. The lake is a popular spot for swimming, boating, and fishing, and features a public beach and boat launch. Visitors can also take a scenic drive around the lake, which offers stunning views of the surrounding mountains and forests.

10. Kripalu Center for Yoga & Health

For visitors seeking relaxation and wellness, the Kripalu Center for Yoga & Health is a must-see attraction in Stockbridge. The center is located on a beautiful 100-acre campus, and offers a wide range of yoga and meditation classes, as well as workshops and retreats focused on health and wellness. Visitors can also enjoy the center’s spa and wellness services, which include massages, facials, and other treatments.

11. Berkshire Theatre Group

The Berkshire Theatre Group is a professional theater company that produces a wide range of plays, musicals, and other performances throughout the year. The company performs at several different venues in the area, including the Colonial Theatre in downtown Stockbridge. Don’t miss the annual production of “A Christmas Carol,” which has become a beloved holiday tradition in the Berkshires.

12. Housatonic River Walk

The Housatonic River Walk is a scenic walking trail that runs along the banks of the Housatonic River in downtown Stockbridge. The trail offers stunning views of the river and surrounding mountains, as well as opportunities for birdwatching and wildlife spotting.

13. Berkshire Scenic Railway Museum

The Berkshire Scenic Railway Museum is a must-see attraction for train enthusiasts of all ages. The museum is located in a beautifully restored 1903 train station, and features a collection of historic train cars and locomotives. Visitors can take a scenic train ride through the Berkshires, and learn about the history of rail travel in the area.

14. Berkshire Museum

The Berkshire Museum is a family-friendly museum located in downtown Pittsfield, just a few miles north of Stockbridge. The museum features a wide range of exhibits, including natural history displays, art exhibits, and interactive science exhibits. Don’t miss the museum’s “Butterflies” exhibit, which features live butterflies and moths from around the world.

15. Tanglewood

Tanglewood is one of the most iconic attractions in the Berkshires, and is located just a few miles outside of Stockbridge. The outdoor amphitheater is the summer home of the Boston Symphony Orchestra, and hosts a wide range of concerts and other performances throughout the season. Visitors can bring a picnic and enjoy a concert under the stars, or explore the beautiful grounds and gardens of the Tanglewood estate.

16. Lee Premium Outlets

For visitors seeking a shopping fix, the Lee Premium Outlets are a must-see attraction just a few miles south of Stockbridge. The outlet mall features over 60 stores, including designer brands like Michael Kors, Coach, and Polo Ralph Laure .