Local Events & Attractions

Lenox is your stepping-stone to the heart of the Berkshires in western Massachusetts. Located just outside the charming town of Lenox, the beautiful Bellefontaine Mansion, built in 1897, offers a classic vacation destination in an area renowned for culture and scenic beauty.

No matter when you choose to visit, there’s always lots to do in the Berkshires – from the annual performing Arts Festival at Tanglewood and other cultural venues to local events with a New England flavor. Below are some of our favorites; for more details visit Berkshires.org or lenox.org. The local listings on these links are updated often, so keep checking for exciting new additions. 

Year-round

Norman Rockwell Museum
The museum is dedicated to education and art appreciation, inspired by the legacy of beloved artist and former Berkshires resident Norman Rockwell.

Berkshire Botanical Gardens
The public display gardens, on 15 acres of cultivated land, are among the oldest in the United States. They feature more than 3,000 species and varieties of plants to be found in the Berkshires.  Classes, workshops, lectures and special events are offered throughout the year.

January

Ski the Berkshires
The ski areas of the Berkshires have something for all the family. With noteworthy children’s and learning programs, as well as moguls and black diamond runs, it’s perfect for skiers of all ages and abilities.

February

10x10 Play Festival
A new play begins every 10 minutes! Join us at St. Germain Stage for an evening of ten 10-minute plays by 10 playwrights, featuring dynamite actors, as part of the 10x10 Upstreet Arts Festival.

Thunderbolt Ski Race & Thunderfest Winter Festival
Admission is free for everyone who wishes to watch the Thunderbolt Ski Race from Greylock Glen at the foot of the mountain in Adams. Parking is limited, but free shuttles are available.

May

Annual Memorial Day Marathon Races
The races start and finish at the iconic Tanglewood Music Center. They include the Memorial Day Marathon and Half Marathon, the Berkshires 10k and 5k, the MDM 15k Trail Race, the MDM Trail-Road Challenge, the Berkshire Bank Kids’ Run and the MDM Pre-Race Expo at Tanglewood.

Berkshire International Film Festival
A world-class festival celebrating independent, feature, documentary and short films. Panel discussions, special events and more. Great Barrington and Pittsfield.

June

A Prairie Home Companion
Enjoy a recording of the popular radio variety show A Prairie Home Companion, live from Tanglewood, hosted by humorist Garrison Keillor.

Audra McDonald in Concert
The two-time Grammy® Award winner will perform an intimate evening of favorite show tunes, classic songs from movies and original pieces written for this extraordinary artist.

Berkshire Cycling Classic Cyclosportif
This annual cycling event in Lenox, Massachusetts, will feature routes of 62 and 81 miles (100k and 31k). The long and hilly routes provide the perfect settings for those who wish to test their legs in a friendly and competitive atmosphere.

Wilco Solid Sounds Music Festival
Curated by Wilco, the Solid Sound Festival returns with a sparkling lineup of musicians, comedians and visual artists.

July

Much Ado About Nothing
The dazzling love story between the headstrong Beatrice and confirmed bachelor Benedick is set against a darker story of intrigue and deceit. At once heartfelt and exhilarating, Much Ado is filled with some of the most brilliant comedic repartee ever written.

Opening Night at Tanglewood
Boston Symphony Orchestra with Rafael Frühbeck de Burgos, conductor, and Joshua Bell, violin. All-Tchaikovsky program. Violin Concerto Symphony No. 5.

August

Annual Berkshires Crafts Fair
The Berkshire Crafts Fair is a juried show of master artisans offering traditional and contemporary jewelry, furniture, ceramics, textiles, glassware, woodwork and more. Proceeds benefit innovative initiatives and programs at Monument Mountain Regional High School.

Annual West Stockbridge Zucchini Festival
This fun-filled, family-friendly summer festival features a pet parade and show, game and craft booths, Queenie Zucchini Costume Contest, a Zucchini Weigh-Off, races, great food, live music and fireworks.

Festival of Contemporary Music
Directed by Pierre-Laurent Almard, the Festival highlights the works of composers Helmut Lachenmann and Marco Stroppa, with performances of music of Gyorgy Logeti, Conlon Nancarrow, Steve Reich and more. The festival will conclude with the U.S. premiere of George Benjamin’s critically acclaimed opera Written on Skin in a concert performance.

John Williams’ Film Night
For the ever-popular Film Night, John Williams and the Boston Pops will be joined by guest conductor David Newman and renowned vocalist Audra McDonald for what has become one of the signature events of the Tanglewood season.

September

Annual Josh Billings Runaground Triathlon
Renowned humorist Josh Billings was better known in his day than his contemporary, Mark Twain. One of his sayings, “To finish is to win”  is the motto of his namesake Runaground Triathlon. “The Josh” is an event for all ages and abilities, fun both for participants and spectators.

Berkshires Arts Festival
Featuring artists from across the nation, this annual festival has become the chosen daytime weekend attraction for thousands of art lovers each year. 

Fall Foliage Parade & Festival
The annual Fall Foliage Parade in North Adams focuses this year on transportation. Expect to see vehicles of all kinds – from cars and bicycles to planes, trains and balloons. Before the parade, enjoy an Autumn Arts Festival Craft Fair, the annual leaf hunt and a charity bed race.

Founder’s Weekend Celebration
This celebration of the 230-year-old town of Lee features a cornucopia of fun events, from bake sales, children’s activities and face painting to tap dancing on Main Street, live acoustic music, tours of a historic church and a pumpkin carving contest.

Historic Lenox Horse-Drawn Carriage “Tub” Parade
Experience the annual Tub Parade, a Berkshires tradition for more than a century. Small, open horse-drawn carriages known as “tubs” are decorated and driven by riders in period costumes.

Lenox Apple Squeeze, Harvest Festival
Enjoy all things apple during this annual celebration – including apple pies, apple cider and even apple pizza. There will also be hay and pony rides, a children’s dog show, craft demonstrations, sidewalk sales and more.

October

Berkshires Coaching Weekend
Coaches drawn by teams of horses drive to a different venue each day for a presentation of the coaches. A coach horn competition on Saturday strikes the keynote for this unique event. On Sunday, the Cantilena Chamber Choir presents Music of the Gilded Age at Trinity Church in Lenox.

Traditional Shaker Supper
In a guided tour before supper, interpreters in period costume will introduce you to Shaker life as you view the village’s premier collection of Shaker furniture and artifacts. A cider and cheese reception precedes a candle-lit buffet supper featuring traditional Shaker fare.

November

Festival of Trees at Berkshire Museum
See 100+ dazzling holiday trees, each uniquely decorated by local businesses, schools and community organizations. Enjoy special events throughout the Festival, with a visit from Santa, cookie decorating, a family day, a performance of holiday music and more.

December

Gingerbread House Contest at Lenox Library
The sweetest event of the year at Lenox library – the Gingerbread House Contest attracts entries from some of the Berkshires’ most inspired amateur and professional chefs  in a festive display of edible architecture.

Lenox Caroling Festival
Catch the spirit of the season with the Lenox Caroling Festival – an old-fashioned New England gala weekend filled with holiday events.

Santa Arrives for Town Tree Lighting
Don’t miss the annual Christmas Tree Lighting ceremony. Following the lighting at Veterans Memorial Park, Santa will greet children at the Fire Station on Elm Street, where gifts and refreshments will be distributed. Children can also get their photos taken with Santa.

The Inns of Lenox Holiday Tour
Tour some of Lenox’s most historic inns as choirs fill the streets during this festive event. Tour tickets may be purchased in advance.