Downtown Pittsfield Festive Frolic
2025-12-05, 2025-12-06 | Downtown Pittsfield, Downtown Pittsfield, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. (DPI) will host the Downtown Pittsfield Festive Frolic on Friday and Saturday, December 5 and 6. Activities will include the City of Pittsfield’s Park Square Tree Lighting Ceremony, Free Hot Chocolate and Photo Ops with The Grinch at Otto’s, The Berkshire Bazaar hosted by Thistle ‘n Thorn Floral at The Holiday Inn, Photo Ops with Santa, A Free Kids’ Paint & Sip, The City of Pittsfield’s Wreath Art Auction at the Lichtenstein Center for the Arts, and much more.
The City of Pittsfield’s Park Square Tree Lighting Ceremony will be on Friday, December 5 starting at 6 pm. Join Santa, Mrs. Claus, and the City of Pittsfield’s Recreation Department for this festive holiday tradition. The Pittsfield High School Chorus will perform a variety of carols around 5:45 pm before the ceremony begins, and Santa and Mrs. Claus will arrive following the tree lighting. Lipton Market will be providing free hot chocolate and coffee in Park Square during the event.
Those planning to attend the ceremony are asked to bring non-perishable food items that will be donated to the Christian Center’s food pantry.
Artists Peter Vacchina and Robert Markey will be creating holiday-themed ice sculptures in Park Square beginning at 5 pm. Their live ice sculpting will continue throughout the evening for attendees to watch, subject to favorable weather conditions.
Otto’s Kitchen & Comfort, 95 East Street, will be providing free hot chocolate and photo ops with the Grinch from 5 to 8 pm on Friday, December 5.
The Festive Frolic continues Saturday, December 6, with The Berkshire Bazaar hosted by Thistle ‘n Thorn Floral at The Holiday Inn, 1 West Street, from 11 am to 4 pm. Shop handmade goods and thoughtful gifts from dozens of local makers, artists, and small businesses.
Downtown Pittsfield, Inc. and St. Stephen’s Episcopal Church will host a Free Kids’ Paint & Sip on Saturday, December 6, 12:30 to 3 pm, in the auditorium at St. Stephen’s Episcopal Church, 67 East Street.
This free holiday-themed Paint & Sip is best suited for ages 5 to 12, although younger and older children are welcome. All materials, snacks, and juice will be provided. Children will be provided with a small canvas and wooden ornament for painting. The Berkshire Museum will be joining in on the fun with a free yarn snowflake ornament craft.
Children are welcome to drop in anytime over the course of the event, and all children must be accompanied by an adult. The auditorium is on the second floor of the parish house, and the entrance is on Allen Street.
Downtown Pittsfield, Inc. will also host Photo Ops with Santa on Saturday, December 6, 12:30 to 3 pm, outside in Dunham Mall at 100 North Street.
Santa will be welcoming children and families to visit with him and take photos. Please bring your own camera or cell phone to capture your own photos of this special moment. There will not be a photographer on site.
Hand Crafted, 26 Dunham Mall, will be handing out free hot chocolate and cider to all in attendance, and Downtown Pittsfield, Inc. will be handing out free Winston Ornaments while supplies last.
Berkshire Community Action Council (BCAC) invites you to help support the Elf Children’s Warm Clothing Program by bringing a NEW winter coat or pair of boots to Dunham Mall for a child in need. If you do, you’ll earn an entry into a raffle to win a luxurious one-night stay at Hotel on North. BCAC will also be giving away free cookies to all. The raffle drawing will be at 3 pm, and you do not need to be present to win.
Hot Plate Brewing Co., 1 School Street, will present free live music in their taproom from 1 to 3 pm featuring JJ Slater, a song-singer, guitar-picker, and storyteller from the swampy side of New England.
The Berkshire Carousel at 50 Center Street will celebrate the Festive Frolic with Donkey Day on Saturday, December 6 from 12 to 5 pm. There will be free rides in celebration of Missy the Donkey sponsored by author Kevin O’ Hara. Kevin will introduce his latest book, and there will be a special dance performance.
SOLARIUM Plant Shop, 46 West Street, invites children to drop-in to make free dried floral ornaments from 12:30 to 3 pm on Saturday, December 6.
Indie Readery and Records, 314 North Street, and Drag Story Hour Berkshires will present a holiday-themed Drag Story Hour with Sativo Green from 1 to 2:30 pm on Saturday, December 6.
The Berkshire Athenaeum, Pittsfield’s Public Library, 1 Wendell Avenue, will offer free drop-in activities for all ages from 12:30 to 3 pm on Saturday, December 6. The Children’s Library will host a fun winter craft, the Young Adult Department will offer a button-making craft, and there will be festive bookmark making for adults and teens in the Blake Room.
This year, the Lichtenstein Center for the Arts, 28 Renne Avenue, will host its 11th annual Wreath Art Auction to benefit the Pittsfield Community Food Pantry on a SATURDAY. Join the Office of Cultural Development for this holiday tradition on Saturday, December 6 from 4 to 6 pm. Grab and go wreaths will be available starting at 4 pm, and the top items will be auctioned off at 5:30 pm.
Dozens of local artists have donated their talent, time, and materials to create one-of-a-kind, original holiday wreaths, centerpieces, kissing balls, and more. There will also be a raffle to win some amazing gifts from local businesses, and all of the proceeds from the event will benefit the Pittsfield Community Food Pantry which serves over 1200 families a week in Pittsfield. $10 suggested donation at the door.
The Albany Berkshire Ballet (ABB) is bringing back its Annual Tour of the holiday classic The Nutcracker to The Colonial Theatre on Friday, December 5; Saturday, December 6; and Sunday, December 7. Choreographed by ABB’s Artistic Director Madeline Cantarella Culpo, the production features lavish sets and scenery designed by Stockbridge native and renowned theater and movie set designer Carl Sprague, as well as costumes designed by Sam Meredith. In this performance, young local dance students will share the stage with professional ABB dancers, portraying special children’s roles. This year’s company includes international dancers as well as dancers from around the United States. For tickets, visit berkshiretheatregroup.org.
For more information on the Downtown Pittsfield Festive Frolic, visit downtownpittsfield.com or call Downtown Pittsfield, Inc. at 413-443-6501.
The mission of Downtown Pittsfield, Inc. is to strengthen and promote Downtown Pittsfield, Inc.’s membership through advocacy, collaboration, and celebration.
Since 1983, Downtown Pittsfield, Inc. (DPI) has been the recognized leader, facilitator, and principal advocate for downtown. DPI is a membership organization consisting of property owners, businesses, residents, cultural & entertainment venues, restaurants, and non-profit organizations who have joined forces to increase economic activity by promoting downtown as a great place to live, work, and play.

13th Annual Christmas Tree & Wreath Festival
2025-12-06 10:00 - 15:00, 2025-12-07 10:00 - 15:00, 2025-12-13 10:00 - 15:00, 2025-12-14 10:00 - 15:00 (America/New_York) | Palmer Historical and Cultural Center, 2072 Main St., Three Rivers, MA, 01080, United States
Mark your calendars! The 13th Annual Christmas Tree & Wreath Festival is right around the corner.
Festival Dates: Dec 5 | 4–7 PM & Dec 6–7 | 10 AM–3 PM & Dec 13–14 | 10 AM–3 PM
Location: Palmer Historical & Cultural Center, 2072 Main St., Three Rivers
Stop by during the festival to purchase raffle tickets for your chance to win a gorgeous, decorated tree or festive wreath – each one handcrafted by individuals, businesses, and community groups.
Raffle tickets: $1 each or $5 for 10
Bring new and unwrapped toys to donate to the Lions Club of Palmer Toy Drive and receive a free raffle ticket (for each donated toy) as a thank-you for helping local families in need!
More info: https://palmerhcc.org/events/

Women of Impact 2025
2025-12-09 17:30 - 21:00 | Twin Hills Country Club, 700 Wolf Swamp Rd, Longmeadow, MA, 01006
Ticket sales have ended, but if you have any questions or would like to join the wait list, email Natasha Mercado, Marketing and Events Manager, at mercado@businesswest.com or call (413) 781-8600 ext. 100
In 2018, BusinessWest created the Women of Impact program as a way to honor women in the region who are making an impact and creating positive change. There are so many different ways to do this. While nominees can hail from the world of business, they can also emerge from other realms, such as the nonprofit community, public service, law enforcement, education, social work, the mentorship community, a combination of these — in short, we’re recognizing inspirational women on any level.

PrideLands: White Lion Wednesday (Outdoors)
2025-12-10 16:30 - 21:00, 2025-12-17 16:30 - 21:00, 2025-12-24 16:30 - 21:00, 2025-12-31 16:30 - 21:00, 2026-01-07 16:30 - 21:00, 2026-01-14 16:30 - 21:00, 2026-01-21 16:30 - 21:00, 2026-01-28 16:30 - 21:00 and 1 more date | Tower Square Park, 1500 Main St, Springfield
The iconic White Lion Wednesday kicks off the event week with music, food, games, and social interaction at 1477 Main Street (Tower Square Park).
4:30pm until 9pm.
Weekly Entertainment, cigar bar, games, etc.

Mindful Childbirth & Parenting: 8 Week Course
2025-12-12 10:00 - 2026-01-30 12:30, 2025-12-19 10:00 - 2026-02-06 12:30, 2025-12-26 10:00 - 2026-02-13 12:30, 2026-01-02 10:00 - 2026-02-20 12:30, 2026-01-09 10:00 - 2026-02-27 12:30, 2026-01-16 10:00 - 2026-03-06 12:30, 2026-01-23 10:00 - 2026-03-13 13:30, 2026-01-30 10:00 - 2026-03-20 13:30 | Sunderland Library, 20 School St, Sunderland, 01375, United States
Join other expectant parents in this groundbreaking, 8-week in-person mindful birthing course led by Brigid Owino of Perinatal Wellness Partners. Learn to engage the mind to work with pain, fear, and anxiety during labor while increasing confidence and courage for the experience of labor and delivery. This course can also carry you through the early stages of parenthood. Partners are welcome to join.
In this Mindfulness-Based Childbirth and Parenting (MBCP) course, learn to:
Access deep physical and mental relaxation
Engage the mind to work with pain during labor
Increase confidence and courage for the experience of labor and delivery
Practice prenatal movement for strength and flexibility
Develop skills for managing stress in pregnancy, parenting, and daily life
Enhance partner communication skills
Become more aware of your own approach to parenting
Registration is required; sign up here: https://calendly.com/sunderlandpubliclibrary/childbirth?month=2025-09

Designer Purrrse Bingo
2025-12-12 18:00 - 22:00 | Springfield Elks Lodge, 440 Tiffany Street, Springfield, MA, 01108
Get ready for a glamorous night out with a cause! Join us Friday, December 12, 2025 at the Springfield Elks for Designer Purrrse Bingo, an unforgettable evening benefiting the animals in need at the Foundation for TJO Animals. Doors open at 6:00 PM, the first game starts at 6:45 PM — and trust us, this is not your grandma’s bingo.
✨ What’s in store:
Each ticket includes a 10-game packet & dabber to mark your cards.
NEW this year: two designer bags per round—double the fun, double the stakes!
Featuring an exclusive Louis Vuitton Bonus Game (purse lovers, this one’s for you).
Door prizes, raffles, refreshments, and a cash bar to toast your wins.
Plus an Adopt & Rescue Bag Raffle Table — score a stylish statement piece, while supporting rescue efforts.
🎤 Emceed by Leah Rantz of Lazer 99.3 — bringing the energy, the laughs, and maybe a few surprises.
💵 Price info & extras:
Tickets: $50 each
Want to bring your friends? Grab a table for 10 seats for $450
Add-ons: more bingo packets, extra cards, special game cards (including that LV game) all available
Come for the purses. Stay for the paws. Help animals get the care they deserve. Let’s make it a night to remember — stylish, fun, and full of heart.
*If you’re interested in being an event sponsor, please contact jbrown@tjofoundation.org. We are still looking for our Partner sponsor, which features a full program add, table signs and more!

Four Rivers Charter Public School Admissions Information Session
2026-01-07 18:00 - 19:30, 2026-01-28 18:00 - 19:30, 2026-01-31 10:00 - 11:30 | Four Rivers Charter Public School, 248 Colrain Rd, Greenfield, MA, 01301, United States
Learning that matters. Belonging that lasts. Four Rivers Charter Public School serves students in grades seven through twelve across Franklin County and beyond. Come join an in-person admissions information session to learn about what our school has to offer!
Four Rivers is accepting applications for the 2026-2027 academic year. Attending an information session is strongly recommended for interested students and their families. These sessions include a presentation by students and staff, a tour of our campus and facilities, and time for questions and refreshments. Information sessions are the best way to learn about Four Rivers, our community, and how we build our programming around the EL Education (formerly expeditionary learning) school model.
Any unexpected changes, such as postponement due to weather, will be emailed to families and posted on our website.
Preregister at the link on our website (optional).

MLK Day 2026!
2026-01-19 12:30 - 16:00 | MassMutual Center
MLK Day is January 19, 2026!
Each year, as we gather to honor the life and enduring legacy of Dr. Martin Luther King Jr., we are reminded of the life, legacy and unshakeable moral leadership of Rev. Dr. Martin Luther King, Jr. This year’s theme, “Restoring Justice. Reclaiming the Dream.,” invites us all to rise together in a moment when Dr. King’s vision urgently calls for renewed commitment, courage, and collective action.
The MLK Day Collaborative invites you to “MLK Day 2026: Restoring Justice. Reclaiming the Dream.” On Monday, January 19, 2026 at the MassMutual Center for an Arts & Wellness Expo from 12:30pm to 2:00pm with the program beginning at 2:00pm.
12:30 – 2:00pm – Arts & Wellness Expo, MassMutual Center
2:00 – 4:00pm – MLK Day Program, MassMutual Center
All are welcome as we open the doors of the MassMutual Center to the public at 12:30pm with artistic expressions, exhibitions, and vendors in the lobby entrance followed by an awe-inspiring, purpose driven program where over 800 youth and supporting adult participants will manifest our theme through inspiring spoken word, dance & music presentations featuring: MLK Charter School of Excellence, Martin Luther King Jr. Family Services’ Youth & Clemente Program, Community Music School of Springfield’s Sonido Musica, String City Festival Orchestra, Springfield CommUnity Chorale, Children’s Chorus of Springfield, Springfield Public Schools students, and more. See full event website for all updates and information.
The MLK Day Collaborative is comprised of the following organizations: ​City of Springfield, Community Music School of Springfield, D.R.E.A.M. Studios,​ FOCUS Springfield, Inclusive Strategies, Legacy Sounds, ​Martin Luther King Jr. Family Services, Martin Luther King Jr., Charter School of Excellence, ​NAACP of Springfield, Parent Villages, Springfield College, Springfield Public Schools, ​Springfield Cultural Council, Springfield Cultural Partnership, Trust Transfer Project, Urban League of Springfield, Young At Heart Chorus, and Inclusive Strategies, who are all working in unity together to ensure this is a memorable community experience.
This collaboration demonstrates the power of coming together, transcending boundaries, and working toward the common goal of justice with and for our Beloved Community. Let’s demonstrate the power of empowering youth leadership, amplifying community voices, and sustaining the momentum of Dr. King’s dream in our region. Together, we reclaim the Dream!
This is a free event and open to the public.

“A Taste of Downtown” – a month-long Downtown Restaurant Celebration
2026-02-01 - 2026-02-28 | Downtown Pittsfield, Downtown Pittsfield, Pittsfield, MA, 01201, United States
In February 2026, Downtown Pittsfield, Inc. will present “A Taste of Downtown” – a month-long Downtown Restaurant Celebration – in partnership with Mill Town Foundation. Eighteen restaurants and bars in downtown Pittsfield will be participating.
“A Taste of Downtown” will feature marketing efforts to highlight downtown Pittsfield’s local restaurants and the Taste of Downtown Giveaway which will be an incentive for people to dine in local restaurants over the course of the month.
The prize for the Taste of Downtown Giveaway will be 18 gift cards – one from each of the participating restaurants – an over $400 value. Every purchase at a participating restaurant will count as one entry to win the prize package. Ask your server for the QR code to enter the contest at the time of purchase. There is no limit to the number of entries per location.
A winner of the Taste of Downtown Giveaway will be drawn at random at the beginning of March.
Restaurants participating in “A Taste of Downtown” include:
101 Restaurant & Bar, 1 West Street
BB’s Hot Spot at The Lantern, 455 North Street
Brazzucas Market, 75 North Street
Dottie’s Coffee Lounge, 444 North Street
Dre’s Global Kitchen, 137 North Street (OPENS 2/13) <Enjoy double entries here to celebrate this new business!)
Espetinho Carioca, 48B North Street
Hot Harry’s, 37 North Street
Hot Plate Brewing Co. , 1 School Street
Marie’s North Street Eatery and Gallery, 146 North Street
Marketplace Café, 53 North Street
Methuselah Bar & Lounge, 391 North Street
Otto’s Kitchen & Comfort, 95 East Street
Patrick’s Pub, 26 Bank Row
RARE 297 Steakhouse, 297 North Street
RJ’s Restaurant, 109 First Street
South Street Pizza House, 148 South Street
Tito’s Mexican Bar & Grill, 34 Depot Street
WANDER Berkshires, 34 Depot Street, Suite 101
“A Taste of Downtown” is sponsored by Downtown Pittsfield, Inc. and is presented in partnership with the Mill Town Foundation.
Follow @downtownpittsfield on Facebook and Instagram for “A Taste of Downtown” restaurant spotlights.
