Holiday Events

Need help with Holiday Gift giving? Our Berkshires Holiday Auction is the ideal way to purchase the perfect Hanukkah and Christmas presents.

Ongoing

Berkshire Museum’s Whimsical, Wonderful Festival of Trees, Pittsfield
Tap into a world of dreams at the Whimsical, Wonderful Festival of Trees. The annual event will feature more than 100 dazzling decorated trees, sponsored by businesses, schools, and community organizations in a true celebration of the holiday season. November 18 – January 7.

Visit with Santa at Ward’s Nursery, Great Barrington
Santa stops in to visit with the young and the young-at-heart customers of Ward’s. His visits start Friday, November 24 and continues on the following Saturdays and Sundays, 11am – 3pm through Sunday December 18.

Tinseliner™ – Celebrating a Vintage American Christmas, North Adams
Get it the spirit of the holidays and take a ride on the Berkshire Scenic Railway Museum’s Tinseliner™, capturing a moment in time and a sense of Christmas nostalgia of years gone by. Traditional holiday music, Santa and more. A great family event! Weekends, November 24 – December 17.

A Christmas Carol, Colonial Theatre, Pittsfield
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. December 9 – 22.

Making Spirits Bright, Lenox
Making Spirits Bright, Dec. 1-3 highlights the holiday season with carolers, inn tours, great shopping and a classic tree lighting to kick-off the season. December 1 – 3.

Stockbridge Main Street Christmas, Stockbridge
Made famous by Norman Rockwell’s painting of the village during the holidays, Stockbridge becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge Main Street at Christmas. The holiday celebration offers a full range of activities, with highlights including holiday readings, house tours, caroling, and a holiday concert. December 1 – 3.

November 12

Holiday Food & Gift Expo, Pittsfield
Get a jumpstart on the holiday season with this festive & FUN event! Sample food & edible gifts plus shop for unique and locally crafted gifts, purchase certificates & much more! 10 AM.

November 18

Berkshire Grown Thanksgiving Holiday Farmers Market, Great Barrington
Featuring locally grown and produced foods and gifts, including fruits and vegetables, cheeses, meats, breads, yarn, and more, plus live music, lunch fare, and children’s activities. At Monument Valley Middle School, 313 Monument Valley Road. Admission is free. 10am – 2pm.

November 19

Berkshire Grown Thanksgiving Holiday Farmers Market, Williamstown
Featuring locally grown and produced foods and gifts, including fruits and vegetables, cheeses, meats, breads, yarn, and more, plus live music, lunch fare, and children’s activities. At Williams College Towne Field House, 82 Latham Street. Admission is free. 10am – 2pm.

November 22

North Adams Annual Tree Lighting, North Adams
Join us at Monument Square on Main Street where residents are asked to gather to count down the seconds until the switch is thrown and thousands of twinkling lights adorn the downtown. From there music will lead the way with festive songs for the North Adams Fire Department’s fire engine as it makes its way through downtown with Santa Claus. Santa and his helpers will bring gifts for the first 500 children.

November 23

Thanksgiving Dining
Blantyre, Lenox
Enjoy an extravagant three-course Thanksgiving feast featuring inspired harvest flavors, traditional side dishes and succulent table-side carved meats. 11 AM – 7 PM.

Cranwell Spa & Resort, Lenox
Thanksgiving Day Buffet Dinner. 11:30 AM – 6:00 PM

Eastover Estate & Retreat Center, Lenox
Celebrate a sumptuous plant-based feast: whole foods, Vegan, Macrobiotic and Gluten-Free featuring organic, locally grown foods and beverages from the Berkshires & beyond. Organic Turkey option for non-vegetarians. 4 PM – 7 PM.

Hotel on North, Pittsfield
Join us for Thanksgiving on North with traditional favorites and more!

Gala Restaurant at Orchards Hotel, Williamstown
Indulge in a buffet dinner that is sure to delight everyone’s appetite. Serving 12:00 PM – 5:00 PM.

Gateways Inn & Restaurant, Lenox
Traditional Thanksgiving dinner with optional choice serving 2 PM – 6 PM. Reservations a must.

Mazzeo’s Ristorante, Pittsfield
Traditional Thanksgiving Dinner. 12 PM – 5 PM

Morgan House Inn & Restaurant, Lee
Thanksgiving Day menu with optional choices.

The Red Lion Inn, Stockbridge
A special prix fixe menu with traditional turkey and enough options to please any palate.

Thanksgiving To Go!

The Marketplace Kitchen, Sheffield
Mazzeo’s Ristorante, Pittsfield
Mezze Bistro+ Bar, Williamstown

November 24

Thanksgiving on the Farm, Hancock Shaker Village, Pittsfield
Enjoy Thanksgiving weekend at the farm. See our heritage breed turkeys in the barnyard and say hello to other animals in the historic Round Stone Barn. Enjoy a peaceful meander along the Farm and Forest Trail, a 1-mile accessible trail. Ski or snowshoe our trails (weather permitting). Learn about the Shakers and see their beautifully-designed objects in the 19thcentury Brick Dwelling on tours of the building at 11am and 1pm. Shop for the holidays in Shaker Mercantile for hand-crafted goods you can’t find anywhere else, several made here by artisans at the Village. Warm up with warm spiced local cider and autumn treats at Seeds Market Cafe.

Visit with Santa at Berkshire Carousel, Pittsfield
Bring the children to visit with Santa, get a candy cane and ride the Carousel! 12 PM – 5 PM.

November 25

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

Murder Mystery Dinner at Ventfort Hall, Lenox
The Comical Mystery Tour ensemble invites the public to join the fun with their holiday program “You Can’t Toy with Death”. The action takes place in the Elfsecutive Board Room, inside the Main Lodge on the Island Of Nitwit Toys. The five characters are Jack in the Boombox, Harry Pothead, Meddle-Lynn, Malibu Bimbi and Stinky Winky the Teleblubby. Cash bar. 5:00 PM.

Visit with Santa at Berkshire Carousel, Pittsfield
Bring the children to visit with Santa, get a candy cane and ride the Carousel! 12 PM – 5 PM.

November 26

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

Children’s Holiday Extravaganza, Colonial Theatre, Pittsfield
Entertainment, Face Painting, Popcorn, Pizza, A Visit from Santa and Mrs. Claus, Raffles and Prizes and More! Children must be accompanied by a parent or guardian. Gift bags will be given out to the first 400 kids. Please bring non-perishable food items for donation. Tickets are available on a first come, first served basis with a limit of 6 tickets per transaction. Free.

Visit with Santa at Berkshire Carousel, Pittsfield
Bring the children to visit with Santa, get a candy cane and ride the Carousel! 12 PM – 5 PM.

November 30

Wreath & Cork at Whitney’s Farm Market, Cheshire
Come enjoy an evening out at the farm with your friends and family! The event includes at 12″ wreath, a bow and all sorts of ornaments to make it your own. There will be samples of wines from many different wineries around the Northern region as well as light refreshments made by our bakery and deli! 6 PM.

Christmas Day & New Year’s Eve Dining

The Williams Inn, Williamstown
Commemorate the Holiday with loved ones with our Family Style Dinner on Christmas Day. 12 PM – 4 PM.

 

December 1

Holiday Tree Lighting, Pittsfield
The community comes together to celebrate the lighting of the City of Pittsfield’s official Christmas tree. The Taconic High School Chorus sings holiday carols, the donor of the tree lights the tree, and Santa & Mrs. Claus make a special appearance.

Holiday Wreath Art Auction at Lichtenstein, Pittsfield
3rd Annual Holiday Wreath Art Auction. Wreaths will be on display in conjunction with First Fridays Artswalk during a ticketed event. Light refreshments and beverages will be served. Preview 5 PM; Auction 6:30 PM.

Historic Deerfield Evening Tour, Deerfield
This holiday season, Historic Deerfield brings the excitement of a 19th-century winter ball to the village with the return of its interactive evening tour, “Getting Ready for a Winter’s Ball.” On this special illuminated evening tour, participants will visit with the 19th-century residents of Deerfield as they get ready for a ball. Along the way they will encounter a variety of scenes capturing the spirit of the evening.

December 2

Holiday Marketplace at Berkshire Botanical Garden, Stockbridge
Holiday Marketplace is the place to shop for unique decorations and holiday trimmings including garlands, flowering plants, swags, centerpieces and one-of-a-kind gifts made by a select group of local craftspeople. New this year is an expanded Gallery of Wreaths located in both the Garden’s Education Center and the newly renovated Center House. Free admission. 11 AM – 5 PM.

Cranwell Holiday Shop & Spa Extravaganza, Lenox
Join us for a day of rest, relaxation and retail. Take advantage of many shopping promotions, meet with our vendors and enter to win fabulous giveaways and raffle prizes valued as high as $800. All shoppers receive an extra ticket for the raffles.

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

Candlelit Evening at Hancock Shaker Village, Pittsfield
Escape the frenzy of modern holidays and experience the magic of an enchanted evening at the Village filled with New England traditions, live music, storytelling, festive food, candlelight, and caroling.

Albany Berkshire Ballet Presents: The Nutcracker, Colonial Theatre, Pittsfield
An annual favorite, the Albany Berkshire Ballet’s Nutcracker tells the story of a young girl, Clara, and the magical dream she has one Christmas Eve.

Annual Handmade Fair at The Outlet @ Pine Cone Hill, Pittsfield
Handmade Fair featuring home and holiday décor, stuffed creatures, jams, sewn & knitted accessories, and more! Purchase from a crafter and get 20% off Outlet store purchases of area rugs, duvet covers, coverlets, pillow covers, loungewear, scarves, decorative pillows, and more. 10 AM – 4 PM.

Williamstown Holiday Walk, Williamstown
Holiday sounds and spirit will fill Spring Street with traditional New England flair: old-fashioned caroling, horse-drawn carriage rides, a Reindog Parade, a Penny Social, Santa Claus, and much more.

Seasons Greetings Family Event at Norman Rockwell Museum, Stockbridge
Enjoy an afternoon of holiday storytelling, art making, tours of Rockwell’s holiday art, and heartwarming treats inspired by Norman Rockwell’s original portrayal of Stockbridge’s historic Main Street, which is on view.

December 3

Holiday Marketplace at Berkshire Botanical Garden, Stockbridge
Holiday Marketplace is the place to shop for unique decorations and holiday trimmings including garlands, flowering plants, swags, centerpieces and one-of-a-kind gifts made by a select group of local craftspeople. New this year is an expanded Gallery of Wreaths located in both the Garden’s Education Center and the newly renovated Center House. Free admission. 10:00 AM – 5:00 PM.

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

Albany Berkshire Ballet Presents: The Nutcracker, Colonial Theatre, Pittsfield
An annual favorite, the Albany Berkshire Ballet’s Nutcracker tells the story of a young girl, Clara, and the magical dream she has one Christmas Eve.

A Celtic Family Christmas, Mahaiwe Performing Arts Center, Great Barrington
Join Natalie MacMaster and Donnell Leahy, the award-winning fiddle virtuosos, in an intimate and unique Christmas concert you will never forget. With the duo accompanied by an incredible array of talented session musicians – and their entire family – A Celtic Family Christmas will guide you into the wonderful world of a true Cape Breton Christmas celebration.

Berkshire Concert Choir at the Festival of Trees, Pittsfield
Join the women of Pittsfield’s own Berkshire Concert Choir as they perform a program of Christmas music from early Renaissance to contemporary compositions. They will sing from repertoire created by des Pez and Hassler, Rutter and Willcocks, Randall Thompson, and more.

Historic Deerfield Evening Tour, Deerfield
This holiday season, Historic Deerfield brings the excitement of a 19th-century winter ball to the village with the return of its interactive evening tour, “Getting Ready for a Winter’s Ball.” On this special illuminated evening tour, participants will visit with the 19th-century residents of Deerfield as they get ready for a ball. Along the way they will encounter a variety of scenes capturing the spirit of the evening.

December 8

BYP’s Ugly Sweater Party!, Pittsfield
Join 1Berkshire Berkshires Young Professionals for a fun evening in your worst gear at Methuselah Bar & Lounge, Pittsfield. The one whose clothing brings the most eye pain, shall be crowned Winner of Terrible Taste! Holiday music, a specialty drink, snacks, seasonal decorations, and a fantastic contest for ugliest sweater. 6 PM – 9 PM.

December 9

The Festival: Time for the Holidays Family Day, Bennington, VT
Bennington Museum invites you to bring the family and enjoy a wonderful day of children’s shopping, Santa, crafts, bake sale and more. Children who bring school supplies or individual non-perishable school snacks for the Seedlings Program are admitted free.

Holiday Shindy, Pittsfield
A magical destination shopping tradition with over 60 artisan vendors, yummy food, warm drinks, and live music. 10 AM – 6 PM.

Happimess at The Colonial Theatre, Pittsfield
We’ll read “The Smallest Elf” by Annie Ingle and then kids will make a felt Christmas tree complete with decorations (and presents!) This craft is seriously adorable and can be used for years to come! Best for ages 3-5 (although toddlers through age 7 are welcome!)

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

Holiday Shop, Sip & Stroll, Great Barrington
Holiday Tree Walk, Holiday Hayrides, Store to Store downtown raffle, Face painting, kids crafts and more! 2 PM – 8:30 PM.

Candlelit Evening at Hancock Shaker Village, Pittsfield
Escape the frenzy of modern holidays and experience the magic of an enchanted evening at the Village filled with New England traditions, live music, storytelling, festive food, candlelight, and caroling.

Souvenir de Florence– An Italian Holiday Celebration, Great Barrington
Presented by Close Encounter with Music, this Italian showcase includes Chrysanthemums, the only chamber music Puccini ever wrote; works by the Venetian Vivaldi; Hugo Wolf’s Italian Serenade, and a Verdi string quartet. Bellissimo!The Amernet String Quartet: Misha Vitenson, violin; Franz Felkl, violin; Michael Klotz, viola; Jason Calloway, cello; with Xiao-Dong Wang, viola; Yehuda Hanani, cello.

December 10

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

Holiday Shindy, Pittsfield
A magical destination shopping tradition with over 60 artisan vendors, yummy food, warm drinks, and live music. 11 AM – 4 PM.

Blind Boys of Alabama Christmas Show, Great Barrington
The Mahaiwe Performing Arts Center presents The Blind Boys of Alabama, who first rose to fame in the south with their thrilling vocal harmonies and roof-raising live show.

December 15

Hannuka Shirei Shabbat at Knesset Israel, Pittsfield
Musical Kabbalat Shabbat Service at 5:30 PM with dinner at 6:30 PM

Miss Bennet: Christmas at Pemberley, Shakespeare & Company, Lenox
This holiday season, join us for a costumed staged reading of this delightful play that revisits your favorite Pride and Prejudice characters as they gather for the holidays.

December 16

Berkshire Grown Holiday Farmers Market, Great Barrington
Featuring locally grown and produced foods and gifts, including fruits and vegetables, cheeses, meats, breads, yarn, and more, plus live music, lunch fare, and children’s activities. At Monument Valley Middle School, 313 Monument Valley Road, Great Barrington. Admission is free. 10am – 2pm.

Jews and Brews at The Well Restaurant, Great Barrington
Join us to meet other Hevreh Hipsters for our first ever 20’s & 30’s meetup, which is guaranteed to be (at least) one crazy night. Young Jews in Berkshire County are invited to shmooze, sing Chanukah songs, eat, drink from our themed cocktail list, play dreidel, and have an all-around miraculous time. Snacks provided and cash bar. 8 Pm – 11 PM.

Miss Bennet: Christmas at Pemberley, Shakespeare & Company, Lenox
This holiday season, join us for a costumed staged reading of this delightful play that revisits your favorite Pride and Prejudice characters as they gather for the holidays.

Holiday Tea at Hancock Shaker Village, Pittsfield
Experience afternoon tea in the historic Brick Dwelling, decorated festively for the holidays. Tea includes an array of sweet and savory bites (you’ll love the Shaker tea cakes!), ending with a behind-the-scenes peek at the upstairs rooms in this beautiful 19th-century dwelling. Two Communal seatings available.

The Nutcracker at Clark Art Institute, Williamstown
Join us for a special encore presentation of the Bolshoi Ballet production of The Nutcracker, screened in HD, in the auditorium. Join us for elegant Nutcracker sweets after the show.

Make a Gingerbread House, Starving Artist Creperie & Café, Lee
Come decorate a homemade gingerbread house with the help of Mrs. Clauss! Must pre-pay to reserve your house! Mrs. Clauss will supply all the frosting and candy you need! $35 per house.

December 17

Berkshire Grown Holiday Farmers Market, Williamstown
Featuring locally grown and produced foods and gifts, including fruits and vegetables, cheeses, meats, breads, yarn, and more, plus live music, lunch fare, and children’s activities. At Williams College Towne Field House, 82 Latham Street. Admission is free.

Chabad Chanukah Family Festival, Pittsfield
A family-friendly Chanukah celebration, highlighted by a public menorah kindling of the holiday’s 6th candle. Community leaders will attend the ceremony and assist in kindling the giant “Menorah of Freedom.” Free and open to the public. Location TBD.

Miss Bennet: Christmas at Pemberley, Shakespeare & Company, Lenox
This holiday season, join us for a costumed staged reading of this delightful play that revisits your favorite Pride and Prejudice characters as they gather for the holidays.

Hancock Holidays at Hancock Shaker Village, Pittsfield
There’s magic in the air. Wreaths on doors. Twinkling lights illuminating the village reminding us of long-ago winter days filled with wonder. Delight in life’s simple gifts, and relax, play, shop, dine, make things, and invent new traditions at the Village. Enjoy warm food and drink at Seeds Market Café.

A Celtic Nutcracker, Mahaiwe Performing Arts Center, Great Barrington
Experience the story of The Nutcracker told through Celtic Dance from the perspective of a young girl living in a cottage in Ireland. Her journey takes her to Tir Na Nog, the land of eternal youth, where she finds herself transformed into a princess and receives gifts from Scottish Sword Dancers, Cornish Dancers, Galician Dancers and more. She even meets a few leprechauns along the way!

December 28

Peter Pan at Clark Art Institute, Williamstown
All children, except one, grow up! Captured live at the National Theatre of London, a recorded (encore) performance of J.M. Barrie’s much-loved tale delights audiences of all ages.