Berkshire Family Fun: Holiday Traditions in the Berkshires

Let the Holidays Begin

Traditions abound in our family beginning with the annual Thanksgiving dinner featuring 25-plus family and friends, mint chip pie, a rousing game of left-right-center and a roundtable discussion of what everyone is thankful for. Soon the holiday books for everyday of December will be wrapped (our own take on the Christmas advent calendar), trees will be chosen, chopped and decorated, and my children’s annual Christmas Eve gift — new pajamas — will be purchased.

Berkshire County is flush with holiday celebrations, many of which have made their way into our family’s list of annual Christmas traditions, and though there are too many to mention them all in this column, here are a few of our favorites.


The Nutcracker, performed by the Albany Berkshire Ballet, will be on stage Dec. 10th & 11th in Pittsfield. (Image courtesy The Colonial Theatre)

The Nutcracker” is a well-known Christmas tradition wherever you live, and for those living in the Berkshires this tradition is kept going each year as a result of the hard work and dedication of the Albany Berkshire Ballet.

The Albany Berkshire Ballet has been bringing its acclaimed production of “The Nutcracker” to audiences throughout the Northeast for over 35 years. Each year, over 600 children are chosen to perform alongside the professional dancers of the ABB in six venues — dancing for over 9,000 audience members. This year’s performances in the Berkshires will take place on Saturday and Sunday, Dec. 10 and 11, at The Colonial Theatre in Pittsfield. — For showtimes and information log onto or


The Santaland Diaries runs Dec. 2nd-3oth in Lenox, MA. (Image courtesy Shakespeare & Company)

Another Berkshire County holiday tradition began last year by way of the legendary Shakespeare & Company in Lenox, and I was lucky enough to partake in it with my husband and friends.

Directed by S&Co. Artistic Director Tony Simotes and starring Peter Davenport, the company presented David Sedaris’ hilarious one-man production, “The Santaland Diaries,” an occasionally subversive, alarmingly clever, engagingly poignant and always side-splittingly funny true account of Sedaris’ time spent working as a Christmas elf at Macy’s Department Store. By the end of the evening my companions and I were rolling in our seats due to the absolute hilarity of seeing this good-looking man deliver a nearly two-hour monologue onstage in his elf costume. We all vowed to return to theater next year during the holidays in hopes of partaking, once again, in our newfound holiday tradition.

This year the show returns this weekend with Simotes once again in the director’s chair and veteran S&Co. funny man Ryan Winkles tackling the role of Crumpet the Elf. The show opens Friday, Dec. 2, and runs through Dec. 30. — For more information log onto S&Co.’s website at


From the Midwest to the Berkshires, local singer-songwriter, Mary Verdi has been bringing people together through her music for years, and for the second year in a row she will bring families together to ring in the holidays at the Colonial Theatre in Pittsfield with a concert titled “Christmas at the Colonial with Mary Verdi.”

The concert is set for 7 p.m., Saturday, Dec. 3, and will feature Verdi and her band, the St. Raphael’s and St. Patrick’s bell ringers from Williamstown, a children’s chorus, the Rock On guitar orchestra, Dalton Ballet Studio dancers, Tony Lee Thomas and, of course, Santa Claus. Audience members will get the opportunity to hear Verdi’s new original song, “Christmas Time,” performed, as the evening will also serve as a celebration of the official release of her new Christmas album “Christmas in the Berkshires.” Later in the concert a children’s cast of elves will take the stage to lead audience members in a heart-warming sing-a-long.

I’m so excited to tell you about this concert as I had the privilege of hanging out with Mary on many occasions, and for the last year I have been getting updates as to the status of this album. I can personally guarantee that this holiday event is sure to fill even the biggest of Scrooges with holiday cheer, and perhaps it could be the beginning of a new holiday tradition for you and your family.

Tickets may be purchased in person at the Colonial ticket office at 111 South St., by calling 413-997-4444 or online at


After nearly 70 years of sitting dormant in the center of Pittsfield, The Colonial Theatre underwent a major renovation and reopened its doors to the public as a theater in 2006. Since its reopening the local theater has been known for presenting stellar family and educational programming at all times of the year. Last year for my twin’s 12th birthday we all took a family “mental health” afternoon to catch Black Violin, two violinists who combine classical music and hip-hop to present a show that is truly out of this world, at the venue. (If they ever return to the area I highly recommend you catch them in action.)

Knuffle Bunny: A Cautionary Musical returns to Western MA on Dec. 4th in Pittsfield. (Image courtesy The Colonial Theatre)

On the agenda for this weekend? The Colonial is presenting a tale of firsts — a stuffed animal’s first trip in the laundry, a little girl’s first words and a Daddy’s first time dealing with his child going “boneless” — in its upcoming musical “Knuffle Bunny: A Cautionary Musical” coming to the Pittsfield theater on Sunday, Dec. 4, at 2 p.m. This musical, based on Mo Willems’ Caldecott Honor-winning picture book, and combines the talents of six-time Emmy Award winner Willems and Grammy Award-winning composer Michael Silversher to lovingly celebrate the heart and heartache that comes from Daddy, Trixie and Trixie’s beloved Knuffle Bunny’s visit to their local laundromat. Tickets can be purchased online at or by calling 413-997-4444.

Another holiday tradition in the Berkshires is the annual holiday performance of Berkshire Theatre Festival’s rendition of the Dicken’s classic “A Christmas Carol,” and since the merger of the company with The Colonial last year to form the Berkshire Theatre Group, the performance has been moved to the Pittsfield venue. This year, patrons who attend one of the 11 scheduled performances will get an extra special treat, as the performance not only feature local residents of all ages, but also local legend James Taylor. (“I see fire and I see rain …”)

Performances are set for Dec. 17-18, 20-23, and 26-30. For more information on performance times and tickets visit The Colonial’s website.


Last year Nicki Wilson and her local theater company Castle Hill Theatre Company, known for putting on a wide selection of professional family theater productions during the year, began a holiday tradition of their own at New Stage Performing Arts Center in Pittsfield with the presentation of Barbara Robinson’s “The Best Christmas Pageant Ever.” This year the company is continuing that tradition with performances of the Christmas-themed musical beginning this weekend on Friday, Dec. 2, and running through Dec. 18.

This holiday production is directed once again by Laurie Ellington and tells the story of the town’s annual Christmas pageant that has always been a sleepy affair —that is, until the Herdman’s catch wind of it. When the meanest, toughest, and wildest kids in town decide that they want to be part of the show, it’ll never be the same again.

Tickets can be purchased by calling 413-418-0999 or online. New Stage Performing Arts Center is located at 55 North Street in Pittsfield.


Every year the Williamstown Holiday Walk, held the first weekend in December, kicks off the holiday season in town. This year’s walk will be held Dec. 2-4 and will begin at 4:30 p.m. Friday evening on Spring Street and beyond. This annual event is meant to draw people to Williamstown for shopping, entertainment, and a fun-filled weekend of holiday cheer. From movie screenings to holiday concerts, alternative gift sales and more, there will be something for everyone in Williamstown this weekend. — For a complete schedule of events visit


I have yet to attend this annual holiday concert, but maybe this year will be the year we work it into our holiday fun list. On Dec. 11 at 3 p.m. Berkshire Lyric and Blafield Children’s Chorus will be joined by the Taconic High School Chorus at St. Stephen’s Episcopal Church in Pittsfield for a traditional/modern holiday concert and a sing-a-long with audience members at 3 p.m. The church is located at Park Square in Pittsfield. For more information call 413-499-0258 or visit


One of our family’s favorite holiday traditions is attending Dalton’s annual Light Up the Holiday’s event, set for Dec. 10, beginning at 5 p.m. and running until 8 p.m.

The event features a plethora of treats, activities, caroling, music, food and more at local businesses for residents and friends of the town while they travel down Main Street to the Dalton CRA for the annual tree lighting.

My kids have had their faces painted like elves and reindeers, sung at stops with school choruses, taken home various balloon animals and left the event each year with their bellies stuffed full of holiday cheer. One of our favorite stops was at the Congregational Church where its bell ringers lead us all in some caroling.

Santa will start at Depot Street and travel up Main Street, making many stops along the way to visit with kids and their parents, before stopping at the CRA for carols and the tree lighting. The only thing that can make this event more festive is the addition of evening snow flurries. Keep your fingers crossed.

For more information visit


From Williamstown to Stockbridge, many Berkshire County towns have their own take on Dalton’s Light Up the Holidays. Williamstown has their annual Holiday Walk (see above), Lenox, a daylong songfest, downtown Great Barrington has its annual Holiday Stroll, and Stockbridge has Main Street at Christmas.

Stockbridge Main Street at Christmas” set for Dec. 4 features antique cars, holiday music, Roger the Jester, Santa’s workshop and more, from noon to 2 p.m. For more information visit or call 413-298-5200.

The Lenox Caroling Festival, a daylong songfest featuring more than 30 choral groups from around the Northeast competing for cash prizes, is set for Dec. 10 from 10 a.m. to 4 p.m. and will be followed by a reception from 6 to 7 p.m. at Shakespeare & Company in Lenox. Visit for more information.

Also on Dec. 10 beginning at 3 p.m. and running until 8 p.m., is the annual Great Barrington Holiday Stroll featuring a library story hour, Berkshire Children’s Chorus, vendors, Santa Claus, children’s activities, music, tree lighting and more. For a complete list of activities visit


Kelly Bevan McIlquham

Kelly Bevan McIlquham writes our bi-monthly column, Berkshire Family Fun, sharing update, events and activities for families in the Berkshires.  Kelly is a freelance writer living in Hinsdale with her husband, Mark, and three children — 12-year-old twins, Max and McKenna, and almost-10-year-old, Shea. She has had her work published in The Advocate, The Family Beat and Berkshires Week out of Berkshire County, and the former Wee Ones E-magazine. She also authors a new blog and Facebook page titled “Renaissance Mom.” — Check out Berkshire Family Fun every other Thursday.

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