Summer events in the Berkshires

5 Best Summer Events in the Berkshires

The Berkshires have long been known as a summer destination for cultural respite. Visitors from Boston, New York City, and other metropolitan cities have seen it as an escape from the hustle and bustle for a welcomed change of pace. Summer events in the Berkshires include incredible art shows and galleries, theatrical performances, concerts by chart-topping artists, and more. You’re never too far from a spectacular experience. The Inn at Stockbridge provides exceptional bed & breakfast lodging for summer visitors and is conveniently located in the heart of all the events happening here. So if you’re looking for a little more culture in your life, visit the Berkshires this summer and check out some of these events and venues during your stay!

Note: Due to the Covid pandemic, some summer 2020 have been cancelled or changed. Please visit each event for full updated info. The Berkshires are open, there’s plenty to see and do, we look forward to welcoming you! The events listed below are 2019 summer season events so you have an idea of what’s normally happening this time of year in the Berkshires.

2019 Summer Events in the Berkshires

Berkshire International Film Festival
Discover Hollywood’s next big break right here in the Berkshires!

1. Berkshire International Film Festival (BIFF)

May 30 – June 2 in Great Barrington, MA
May 31 – June 2 in Pittsfield, MA
Two locations and 68 film events are scheduled for this year’s BIFF in the Berkshires. This world-class festival “is an integral part of the cultural fabric of the Berkshires”. There will be panel discussions and special events highlighting filmmakers and actors in the independent feature, documentary, short, and family film production world. The creators of BIFF hope that guests will come away entertained, educated, and inspired and individuals in the film community will have a chance to collaborate with one another in a celebratory environment. Get your tickets for BIFF today!

2. Tanglewood Season

Held throughout the summer beginning in June in Lenox, MA

Tanglewood is one of the Berkshires most popular attractions in the summer season. With tons of performances by award-winning artists, dancers, orchestras, and more, it is a great place for couples to spend a romantic night, friends to gather and sing along to their favorite songs, and families to reconnect over a picnic meal on the lawn. Guest are encouraged to bring their own blankets, lawn chairs, open-sided canopies, food, and beverages to enjoy on the lawn. There are also a couple of restaurants and concessions available throughout the Tanglewood property. Visit Tanglewood on weekends for special events such as Talks & Walks and Yoga on the Lawn or come during the week and take a tour of the campus to learn about the history. Tickets for performances and events can be purchased here.

Jacobs Pillow Dance Festival
Experience a spectacular live performance at during Jacob’s Pillow Dance Festival

3. Jacob’s Pillow Dance Festival 2019

June 19 – August 25 in Becket, MA

The Berkshires’ premiere summer-long dance festival, Jacob’s Pillow Dance Festival 2019 is staged to wow visitors for its 87th summer with spectacular performances from international artists. From ballet to Spanish-inspired steps to incredible tap performances and acrobatic-style movement, the variety of performances to experience at Jacob’s Pillow are sure to leave you inspired and speechless. Purchase your tickets today and be ready for shows unlike anything you’ve ever seen before!

4. Annual Berkshires Arts Festival

July 5 – July 7 at Ski Butternut in Great Barrington, MA

As their website says, the Berkshires are called “America’s Premier Cultural Resort” and for good reason. This annual event of artists and musical performances is the quintessential cultural event that the Berkshires are best known for. The Annual Berkshires Arts Festival is a showcase of over 40 talented artists from all over the United States. Studio furniture, wearable art, handmade jewelry, glass art, ceramics, paintings, garden sculptures, leather goods, and mixed media are just some of the amazing works of art that you can expect to find at this arts festival in Great Barrington. So if you’re planning to be in the Berkshires over the 4th of July weekend, be sure to add this to your list of things to do in the Berkshires.

Stockbridge Summer Arts and Crafts Festival
Meet artists, admire their work, and maybe make a purchase or two!

5. Annual Stockbridge Summer Arts & Crafts Show

August 17 & 18 on Main Street Stockbridge, MA

Discover one of the best Stockbridge, MA events during your end of summer visit to our inn. The Annual Stockbridge Summer Arts & Crafts Show is a highly anticipated event every year showcasing 85 incredible artists from around the country. Their work ranges from ceramics to wood carvings, furniture to paintings, photography to jewelry, and even specialty foods. Come see Main Street Stockbridge transform into a walkable arts and crafts fair that will surely fill your entire day with plenty to see, explore, and even purchase.