Blog ArchiveHome for the Holidays_ Holiday Happenings in Downtown Pittsfield, MA.

This Holiday Season there are dozens of festive activities, performances, parties, and more for children and adults, all happening in Pittsfield, MA!




Whimsical, Wonderful Festival of Trees 2017

Berkshire Museum

39 South Street. Pittsfield.

Now through Sunday, January 7, 2018. Monday-Saturday, 10 am to 5 pm. Sunday, 12 pm to 5 pm.

Admission: $13 adult, $6 child; Museum members and children age 3 and under are free.


Over 100 dazzling decorated trees, sponsored by businesses, schools, and community organizations, will be on view now through Sunday, January 7, 2018. “The 2017 Whimsical, Wonderful Festival of Trees will be fueled by imagination and tales of fantasy and whimsy, with unlikely marriages of objects, strange juxtapositions, and marvelous scenes. Perhaps the trees will depict a spectacular toy land, a lighthearted garden party, an amusing fun house, or even an enchanted castle. Or maybe they’ll display a collection of holiday keepsakes or a medley of trinkets. Each tree will be a curio cabinet unlike the next: dreamlike, surreal, and extraordinarily odd. New this year, participants were asked to place a unique object or ornament of their choice in their tree for visitors to search for. Inspired by the childhood game of ‘I Spy,’ this year’s Festival of Trees will be a quizzical, fanciful treasure hunt for all to enjoy.”



Hancock Holidays

Hancock Shaker Village

1843 West Housatonic Street. Pittsfield.

Sunday, November 26, 10 am to 4 pm
Saturday, December 2/Sunday, December 3, 10 am to 4 pm
Saturday, December 9/Sunday, December 10, 10 am to 4 pm
Saturday, December 16/Sunday, December 17, 10 am to 4 pm

Adults: $20 ($18 for Seniors, AAA members, MTA cardholders, and active and retired U.S. Military)
Youth: $8 (ages 13-17)
Children: (12 and under) are FREE with a paying adult.


“Celebrate the holiday season at Hancock Shaker Village. There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village. It reminds us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and make memories at the Village. Walk, ski, or snowshoe (weather permitting) our Farm & Forest Trail. Say hello to the baby cows and other heritage breeds that live in our barn. Visit the 19th century Brick Dwelling with a guide (tours at 11 am and 1 pm). Witness blacksmithing demonstrations on Saturdays. Shop for the holidays in Shaker Mercantile for hand-crafted goods you can’t find anywhere else, several made here at the Village. Visit the kids’ holiday craft drop-in workshops Saturdays 11 am-3 pm.”



Sunday, November 26th:


Santa Visits The Berkshire Carousel

The Berkshire Carousel

50 Center Street. Pittsfield.

Sunday, November 26th, 12 pm to 5 pm

Ride tokens are $3 each.


Santa Claus will visit The Berkshire Carousel on Sunday, November 26th from 12 pm to 2 pm and 3 pm to 5 pm. Enjoy a festive atmosphere, visit with Santa, and ride the beautiful hand-painted and hand-carved horses on the carousel!



Monday, November 27th:


Holiday Joy Kickoff Event

Berkshire Athenaeum

1 Wendell Ave. Pittsfield.

Monday, November 27th, 10 am to 12 pm.



The Berkshire Athenaeum has joined forces with the Berkshire Community Action Council, Inc.The Salvation Army Pittsfield Corps; the Christian Center Pittsfield; and the Eagle Santa Fund to provide warm clothing, toys, and food to families who struggle to meet their basic needs.


In a kickoff event at the Berkshire Athenaeum on Monday, November 27th, from 10 am to 12 pm, the Library will unveil a giant tree in their main reading room with tickets that list children’s names to sponsor. There will be carolers, an acting troupe from the Berkshire Theatre Festival, refreshments, and special guest stars, Mrs. Claus and The Holiday Elf.


The Berkshire Athenaeum will be accepting donations of slightly used children’s winter clothing to be donated to the Christian Center in Pittsfield. Sponsors who select a child’s name from the tree should purchase gifts for the child and return the new, unwrapped items to the Salvation Army at 298 West Street or the BCAC at 1531 East Street in Pittsfield.



Friday, December 1st:


Park Square Tree Lighting Ceremony

Park Square. Pittsfield.

Friday, December 1st, 6 pm.



Experience a Pittsfield Holiday Tradition. Enjoy carols performed live by the Taconic High School Chorus. Immediately following the tree lighting, welcome Santa and Mrs. Claus, and enjoy free hot chocolate, courtesy of Patrick’s Pub. In lieu of admission, please bring a non-perishable food item to be donated to the Christian Center’s food pantry.



First Fridays Artswalk: Holiday Edition

Downtown Pittsfield.

Friday, December 1st, 5 pm to 8 pm.



Enjoy a dozen art shows in Downtown Pittsfield during the First Fridays Artswalk and all month long. There will be a free guided walking tour lead by Artswalk co-founder Mary McGinnis beginning at 5 pm on December 1st at the Intermodal Center at BRTA, 1 Columbus Ave.


The Office of Cultural Development will host their third annual Holiday Wreath Art Auction at the Lichtenstein Center for the Arts, 28 Renne Avenue. The wreaths will be on display one night only, in conjunction with First Fridays Artswalk, during a $10 ticketed event, with a preview from 5 pm to 6:30 pm on December 1st. The live auction of 10 featured wreaths will begin at 6:30 pm. Grab and go options also available. All proceeds will benefit the Pittsfield Food Pantries.


NUarts Studios & Gallery, 311 North Street, will host a NUarts Holiday Show on Friday, December 1st, from 5 to 8 pm. There will be interactive art making in the studios of Marney Schorr where visitors can design their own ornaments. Make your own holiday gift tags in the studio of Caroline Kelley. There will be live music by resident musicians Tantrum and Critical Mass, and holiday refreshments will be served.


“Fifth Annual Whimsy” will open at the Whitney Center for the Arts, 42 Wendell Avenue, with an artist reception on December 1st, 5 to 8 pm. This edition of “Whimsy” will feature an intriguing mix of whimsical artwork by Nancy Baumiller, Michael Boroneic, Misa Chappell, Ryder Cooley, Katherine Haig, Don Orcutt, and Marney Schorr. An After Party will follow the reception from 8 to 10 pm with a live multi-media musical performance by the Dust Bowl Faeries.



Saturday, December 2nd:


Annual Family and Friends Handmade Fair

The Outlet at Pine Cone Hill

125 Pecks Road. Pittsfield.

Saturday, December 2nd, 10 am to 4 pm.


The Outlet at Pine Cone Hill will host its annual Handmade Fair on Saturday, December 2nd, from 10 am to 4 pm in their store on Pecks Road. Shop handmade treasures including home and holiday décor, stuffed creatures, jams, and sewn & knitted accessories. Enjoy 20% off Outlet Store purchases with your purchase from a crafter. For more information, visit The Outlet at Pine Cone Hill on Facebook.



Holiday Concert and Sing-along

Berkshire Athenaeum

1 Wendell Ave. Pittsfield.

Saturday, December 2nd, 11 am to 12 pm.



The Berkshire Music School presents a musical winter celebration at the Berkshire Athenaeum on December 2nd! This 45-minute program of holiday music will be performed by youth and adult students of BMS, with a sing-along at the end. BMS faculty members Sherri James Buxton and Bob Shepherd will host.



December 2nd – December 3rd:


The Nutcracker presented by the Albany Berkshire Ballet

Berkshire Theatre Group/The Colonial Theatre

111 South Street. Pittsfield.

Saturday, December 2nd at 2:30 pm & 6:30 pm; Sunday, December 3rd at 1:30 pm & 4:30 pm.

Orchestra: Adults $43.50, Children $28.50
Balcony: Adults $41.50, Children $26.50
Gallery: Adults $ 29.50, Children $20.00


Enjoy the Albany Berkshire Ballet’s annual touring production of The Nutcracker in the ambiance of the beautiful Colonial Theatre in Downtown Pittsfield. Local dance students in special children’s roles will be featured alongside the professional and international dancers of the Albany Berkshire Ballet. Choreographed by Artistic Director, Madeline Cantarella Culpo, sets and scenery by Carl Sprague, and costume design by Rita Watson and Victile Donahue.


The Nutcracker tells the story of a young girl, Clara, and the magical dream she has one Christmas Eve. Set to Tchaikovsky’s timeless music, the story of The Nutcracker follows the adventures of Clara and her Nutcracker Prince as they conquer the Mouse King and embark on magical journey to The Land of Sweets.”



Sunday, December 3rd:


Berkshire Concert Choir at the Festival of Trees

Berkshire Museum

39 South Street. Pittsfield.

Sunday, December 3rd, 3:30 to 4:30 pm.



Pittsfield’s Berkshire Concert Choir will perform a program of Christmas music spanning from early Renaissance to contemporary compositions; singing pieces created by des Pez and Hassler, Rutter and Willcocks, and Randall Thompson among others.



Friday, December 8th:


BYP’s Ugly Sweater Party!

Methuselah Bar and Lounge

391 North Street. Pittsfield.

Friday, December 8th, 6 pm to 9 pm.

$10 for BYP members and $15 for guests.


Join 1Berkshire’s Berkshire Young Professionals for a light-hearted ugly sweater party in the back room of Methuselah Bar and Lounge. Enjoy holiday music, a specialty drink, snacks, seasonal decorations, and a contest for ugliest sweater. Cash bar. $10 for BYP members and $15 for guests. Bring your business cards to be entered to win a door prize!



Saturday, December 9th:



The Garage (Berkshire Theatre Group/The Colonial Theatre)

111 South Street. Pittsfield.

Saturday, December 9th at 10 am.

Each child is $10. Parents are free. Includes complimentary coffee for parents.


Children will enjoy story-time with a reading of the “The Smallest Elf” by Annie Ingle; then make a felt Christmas tree complete with decorations and presents! To register your child, email [email protected] or call/text 413-822- 7902. Best for ages 3-5 (although toddlers through age 7 are welcome).



David Grover’s Free Children’s Concert

The Garage (Berkshire Theatre Group/The Colonial Theatre)

111 South Street. Pittsfield.

Saturday, December 9th at 11 am.



Berkshire favorite, David Grover, will perform a free children’s concert on December 9th, accompanied by his daughter Jessica on bass. David has played extensively with many famous musicians, but his ability to connect with fans of all ages is his greatest accomplishment!

Call the Box Office at 413-997-4444 to reserve your free tickets. 6 tickets per transaction.



Holiday Gift Making Day

Berkshire Paint and Sip

305 North Street. Pittsfield.

Saturday, December 9th, 1 pm to 3 pm.



Ages 6 to adult are welcome at Berkshire Paint and Sip’s Holiday Gift Making Day! For $35, choose 4 items to paint. Choose from glasses, mason jars, vases, ornaments, and more. All painting materials, a light snack, and instruction are included. BYOB.



December 9th – December 22nd:


A Christmas Carol

Berkshire Theatre Group/The Colonial Theatre

111 South Street. Pittsfield.

Multiple Performance Times.

Tickets: Adults: $38. Children 16 and under: $28.

*Tickets to the Special Community and Sensory-Friendly Performance on December 13 at 7 pm: $5


“Celebrate the timeless holiday tradition of A Christmas Carol with the whole family, and revel in the joy and redemptive power of Christmas as told in the timeless tale of Ebenezer Scrooge, the infamous miser who is shown the error of his ways and reformed by four spirits. Journey back to Victorian England and experience the classic story filled with holiday carols and the wonderment of the season.”


This production is adapted by Eric Hill from the novel by Charles Dickens and is directed by Travis G. Daly.


*“Berkshire Theatre Group presents a special community and sensory-friendly performance of A Christmas Carol on Wednesday, December 13 at 7 pm, at The Colonial Theatre. A “sensory-friendly” performance is a production that is slightly modified to accommodate individuals with sensory-input disorders, such as people on the autism spectrum. At this performance, you will notice relaxed “house rules;” people may need to get up, move around, and leave the theatre during the performance. There is no expectation that the audience will be completely quiet during the performance. The goal is to create an environment where people with autism or sensory needs, along with their families, can enjoy coming to the theatre together and will feel comfortable, supported and free to be themselves.”


Performance Dates:

Saturday, December 9 at 7 pm (Opening)

Sunday, December 10 at 2 pm

Wednesday, December 13 at 7 pm (Special Community and Sensory-Friendly Performance)

Thursday, December 14 at 7 pm (The Great Barrington Rudolf Steiner School Presto String Ensemble, led by Eileen Markland, will perform in the lobby at 6 pm)

Friday, December 15 at 7 pm

Saturday, December 16 at 2 pm and 7 pm

Sunday, December 17 at 2 pm

Wednesday, December 20 at 7 pm

Thursday, December 21 at 7 pm

Friday, December 22 at 7 pm (Closing Performance)



December 9th – December 10th:


Holiday Shindy

Shire City Sanctuary

40 Melville Street. Pittsfield.

Saturday, December 9th, 10 am to 6 pm; Sunday, December 10th, 11 am to 4 pm.

$3 Admission. Children under the age of 12 are free.


The Holiday Shindy is a fantastic and festive craft fair in the repurposed, historic Notre Dame church building. Shop unique and one-of-a-kind gifts from over 60 artisan vendors! Food and warm drinks available. Live music all day.



Sunday, December 10th:


4th Annual All You Can Eat Brunch Buffet with Santa!

Rainbow Restaurant

109 First Street. Pittsfield.

Sunday, December 10th, 11 am to 3 pm.


Enjoy an all you can eat brunch buffet in the company of Santa Claus himself! There will be gifts for the kids and the opportunity to visit and take pictures with Santa!

Reservations are appreciated so Santa can prepare the right amount of goodies for the children!



11th Annual Gingerbread House Decorating Party!!

Dottie’s Coffee Lounge

444 North Street. Pittsfield.

Sunday, December 10th. Kids: 4 to 6 pm. Adults: 6:30 to 8:30 pm.



Create a masterpiece you can eat! Dottie’s will host two gingerbread house decorating sessions on December 10th. $35 admission includes a homemade gingerbread house, frosting, and all the decorations you can imagine! Personal touches are welcomed. Beer and wine will be available for sale at the adult decorating session.

Reservations AND payment in advance are required to secure your spot. You may pay at Dottie’s or call 413-443-1792.



Monday, December 11th:


Terrarium Gift Making Class

Township Four

419 North Street. Pittsfield.

Monday, December 11th, 7 pm to 8:30 pm.
$85 plus tax.


Make a one-of-a-kind gift for the plant lovers in your life! Choose from different containers, plants, and accents; all materials included. Space is limited to eight participants, ages 16 and up. Prepaid reservations are required. Call 413.347.3244, email [email protected], or message through Facebook.



Friday, December 15th:


Berkshire County’s Got Talent

Barrington Stage Company: Boyd-Quinson Mainstage

30 Union Street. Pittsfield.

Friday, December 15th, 6 pm. Doors open at 5:30 pm.


The Berkshire Eagle will present the first annual Berkshire County’s Got Talent on December 15th. Twelve finalists with a variety of talents will perform for a live audience for a chance to win $1000. Purchase tickets at This event is sponsored by Carr Hardware.



Berkshire Lyric Presents: “This Wondrous Night”

St. Mark’s R.C. Church

West Street. Pittsfield.

Friday, December 15th, 7:30 pm.

$20. Children are free.


Join Berkshire Lyric for a night of choral masterpieces in an astoundingly beautiful setting. The Berkshire Lyric Chorus, Melodious Accord, The Blafield Children’s Chorus, and soloists Marjorie Dix, Steve Hassmer, and John Demler will perform under the direction of Jack Brown and accompanist Joe Rose.



Ugly Christmas Sweater Party!

American Legion

41 Wendell Avenue. Pittsfield.

Friday, December 15th, 9:30 pm to 1:30 am.

$7. Ages 21+


Join Weekend Warriors Entertainment for a late night ugly sweater party at the American Legion. Enjoy holiday fun, drinks, music, and dancing! Cash bar. $7 admission. Ages 21+ with valid ID.



December 15th – December 17th:


Noises Off

Berkshire Community College. Robert Boland Theatre.

1350 West Street. Pittsfield.

Friday, December 15th, 8 pm; Saturday, December 16th, 8 pm; Sunday, December 17th, 6 pm.

$15 general admission. $10 students, alumni, staff & senior citizens.


Noises Off is a play within a play. It is about an ambitious director and his troupe of mediocre actors. The cast and crew are putting together a silly sex comedy titled, “Nothing On,” a single-set farce in which lovers frolic, doors slam, clothes are tossed away, and embarrassing hi-jinks ensue. Winner of the 1982 Olivier Award, Best Play!”


This BCC Players’ production is directed by Kevin McGerigle, Technical Director of the Robert Boland Theatre.



Saturday, December 16th:


Free Jingle Bell Run/Walk 2017

Berkshire Running Center

34 Depot Street. Pittsfield.

Saturday, December 16th, 10 am.


Everyone is welcome at Berkshire Running Center’s 6th Annual Jingle Bell Run/Walk! Wear your festive holiday clothes and join friends for a jolly jaunt to raise money for the Eagle Santa Toy Fund!



Kid’s Class: How to Paint “Whimsical Winter Owl”

Berkshire Paint and Sip

305 North Street. Pittsfield.

Saturday, December 16th, 1 pm to 3 pm.


Children ages 6 and up can come to Berkshire Paint and Sip to learn how to paint “Whimsical Winter Owl” on a 16×20 canvas for $25. All painting materials, a light snack, and instruction are included. Adults are welcome to participate.



By contributor Kimberly Cortes-Gritman


Images (left to right): Wreath by Karen Labanaro, Festival of Trees courtesy of Berkshire Museum, Wreath Art Auction photo by katedrewmiller.