Gala Events 2025
February 2025
Romance At The Ranch
Organization: Berkshire HorseWorks
Date: Sunday, February 9th from 11am-1pm
Location: 101 Patton Road, Richmond, MA 01254
April 2025
Get BART Smart, 2025
Organization: BART Charter Public School
Date: Saturday, April 5, 6:00 – 9:00 pm
Location: BART, 1 Commercial Street in Adams
Square Dance & Dinner Community Event
Organization: Berkshire Coalition for Suicide Prevention (BCSP)
Date: April 25, 2025 4-10PM
Location: Stationary Factory, Dalton, MA
Rock & Bowl 2025
Organization: South Community Food Pantry
Date: April 11, 2025
Location: Masonic Temple, 116 South St, Pittsfield, MA 01201
Berkshire United Way Community Celebration
Organization: Berkshire United Way
Date: Wednesday, April 16, 4:00-6:00 p.m.
Location: W A N D E R Berkshires, 34 Depot Street, Pittsfield
May 2025
BerkChique! First Dibs Party
Organization: Ventfort Hall
Date: May 2: 5:30-8:30 First Dibs Party, May 3: 10-4, May 4: 10-2
Location: Ventfort Hall
CATA Gala & Annual Performance Weekend
Organization: Community Access to the Arts
Date: May 10, 2025 at 5pm
Location: Shakespeare & Company, Tina Packer Playhouse, 70 Kemble St., Lenox
June 2025
Gould Farm’s 11th Annual 5K Walk/Run
Organization: Gould Farm
Date: Sunday, June 1st, 2025 from 8AM – 11AM
Location: On our Monterey, MA, campus or virtually participate from anywhere
ViM Live Presents Beyond the Headlines—Constitutional Rights, Public Health & the Power of Narrative
Organization: Volunteers in Medicine
Date: Tuesday June 10, 2025 5:00PM – 9:00PM
Location: The Indigo Room at the Mahaiwe Theater
Great Barrington Public Theater Annual Benefit
Organization: Great Barrington Public Theater
Date: June 14, 2025
Location: St. James Place
2025 Gala
Organization: Berkshire Museum
Date: June 27, 2025
Location: TBD
BOF’s 2025 Gala Libiamo!
Organization: Berkshire Opera Festival
Date: June 1, 2025 beginning at 4pm
Location: Lenox, MA
Summer Gala
Organization: The Mount Edith Wharton’s Home
Date: June 12, 2025
Jacob’s Pillow Season Opening Gala
Organization: Jacob’s Pillow
Date: Saturday, June 21, 2025 from 5:00-11:00pm
Location: Jacob’s Pillow Campus (358 George Carter Rd, Becket, MA 01223)
Shakespeare & Company Annual Gala
Organization: Shakespeare & Company
Date: Saturday, June 28, 2025
Location: Shakespeare & Company, 70 Kemble Street, Lenox MA 01240
I SPY…a party!
Organization: Norman Rockwell Museum
Date: Saturday, June 7, 5pm
Location: Norman Rockwell Museum
Blue Rider Summer Benefit
Organization: Blue Rider Stables, Inc.
Date: June 14, 2025 Mingle with the horses at 5pm, Party starts at 6pm
Location: Blue Rider Stables, 15 Farm Lane, South Egremont, MA
Kids 4 Harmony Summer Gala Concert
Organization: 18 Degrees, Inc
Date: June 24, 2025, reception 5pm, concert 7pm
Location: Tanglewood Music Center, The Tent Club, Ozawa Hall
July 2025
Chesterwood Garden Tea Party
Organization: Chesterwood
Date: July 12, from 3:00 PM to 5:30 PM
Location: 4 Williamsville Road, Stockbridge, MA
Fairview Hospital “Celebrating An Enduring Commitment to Care” 2025 Gala
Organization: Fairview Hospital
Date: Wednesday, July 16, 5:30-8:30 PM
Location: Gedney Farm New Marlborough
20th Anniversary Gala
Organization: Samuel Harrison Society
Date: Saturday, July 12, 2025, 5:30pm – 8:30pm
Location: Berkshire Hills Country Club
BSC Gala 2025
Organization: Barrington Stage Company
Date: Monday, July 21 at 6 PM
Location: Stationery Factory
Mahaiwe 2025 Gala
Organization: Mahaiwe Performing Arts Center
Date: 5pm reception; 6pm dinner; 8pm show Sunday, July 13
Location: Mahaiwe Performing Arts Center
Summer Soiree “Shamelessly Gorgeous”
Organization: WAM Theatre
Date: July 27th, 2025
Location: Dr. Sax House (collaboration with Berkshire Muse)
August 2025
Midsummer Celebration of the Arts
Organization: Becket Arts Center
Date: August 2, 4-6pm (Rain date: August 3)
Location: Private Home (address provided upon RSVP)
Greenagers Summer Gala
Organization: Greenagers, Inc
Date: August 15, 2025 5:30-9 p.m.
Location: April Hill Conservation and Education Center, 62 Undermountain Rd., South Egremont, MA 01258
September 2025
20th Anniversary Gala
Organization: Berkshire International Film Festival
Date: Sunday, September 6, 2026 6pm
Location: A private home in the Berkshires
Berkshire 25
Organization: Berkshire Magazine
Date: September 17 at 5:30pm
Location: Hancock Shaker Village
Celebrate the Berkshires
Organization: 1Berkshire
Date: September 18, 2025, 5-9 pm
Location: Jacob’s Pillow, Becket, MA
Rock the Pantry
A Concert to Benefit the Pittsfield Community Food Pantry (formerly the South Community Food Pantry). Performances by Jackson Ducharme, Wanda Houston Band, Billy Keane, and Natalia Bernal and Jason Ennis
Organization: Pittsfield Community Food Pantry
Date: Saturday, September 20, 2025 at 7:00pm
Location: The Colonial Theatre, 111 South Street, Pittsfield, Mass.
Roots Rising Gala
Organization: Roots Rising
Date: 9/26/2025 6pm
Location: Herman Melville’s Arrowhead 780 Holmes Rd, Pittsfield, MA 01201
October 2025
Toasting & Tasting
Organization: Berkshire South Regional Community Center
Date: Sunday, October 4, 2025 at 5pm
Location: 15 Crissey Road, Great Barrington, MA 01230
BTG Gala
Organization: Berkshire Theatre Group
Date: Saturday, October 11
Location: The Colonial Theatre, 111 South St., Pittsfield, MA
60 Years of Bright Beginnings
Organization: Berkshire County Head Start
Date: 10/11/2025
Location: Hotel on North
Rally for Recover Pickleball Tournament
Organization: The Brien Center
Date: 8am-4pm October 11th & 12th
Location: Bousquet Sport, – 100 Dan Fox Dr., Pittsfield, MA 01201
Generation to Generation, LitNet’s Annual Celebration
Organization: Literacy Network
Date: October 18, 2025 6:00 PM
Location: Bosquet
Grand Opening Celebration
Organization: Berkshire Waldorf High School
Date: October 19, 2025 12-3PM
Location: 6 Main Street, Stockbridge, MA 01262
Fall In Love With BFAIR – One Sip At A Time
Organization: BFAIR
Date: 10/22/25 – 5 – 8 PM
Location: Balderdash Cellars – 81 State Road, Richmond, MA 01254
Masquerade Macabre to Benefit Ventfort Hall
Organization: Ventfort Hall
Date: October 25,2025 7:00-10:00 p.m
Location: Ventfort Hall
November 2025
Music Bingo
Organization: Thanksgiving Angels
Date: November 1, 6pm to 10pm
Location: Berkshire Hills Country Club
Rites of passage and Empowerment fundraiser
Organization: Rites of Passage and Empowerment
Date: Saturday, November 8, 6:00pm
Location: Berkshire Innovation Center
December 2025
Western Massachusetts Association of the Deaf Annual Holiday Luncheon
Organization: Western Massachusetts Association of the Deaf
Date: Saturday, December 6, 2025, from 11:00 AM to 3:00 PM
Location: The Delaney House, 3 Country Club Rd, Holyoke, MA
Gala Events 2024
January 2024
NAACP Freedom Fund Awards
Organization: NAACP, Berkshire County Branch
Date: Saturday, January 20, 2024
February 2024
Stay at Home & Read a Book Ball
Organization: Lenox Library Association
Date: Saturday, February 10, 2024
March 2024
April 2024
Rowdy Rodeo & Auction
Organization: Rotary Club of Pittsfield
Date: April 6, 2024 5PM
Location: Berkshire Hills Country Club
Rock & Bowl Fundraiser
Organization: South Community Food Pantry
Date: Friday, April 12 from 5-8pm
Location: Common Room at Zion Lutheran Church (74 First Street, Pittsfield)
Rococo Raku Revelry
Organization: Berkshire Art Center’s Annual Dance Party
Date: Saturday, April 6th, 7-11pm at the Colonial Theatre
Centennial Celebration
Organization: Berkshire United Way
Date: April 10, 2024, 4:30 PM
Location: The Colonial Theatre, Pittsfield
May 2024
6th Annual Spirit of Caring Awards & Celebration
Organization: Northern Berkshire United Way
Date:Thursday, May 9th – 5:30 – 8:00 at the NORAD Mill
Culinary Arts Apprenticeship Dinner
Organization: Railroad Street Youth Project
Date: Saturday, May 18, 2024
CATA Gala
Organization: Shakespeare & Co.
Date: Saturday, May 11, 2024
The 7th annual Berkshire Nonprofit Awards
Organization: Kripalu
Date: Tuesday, May 21st 9:30-11:30am
An Evening of Well Wishes
Organization: The Brien Center
Date: Thursday, May 16
Location: TBD
June 2024
Spring Fundraising Gala
Organization: Montessori School of the Berkshires
Date: Saturday, June 1, 2024, At Balderdash Cellars
Great Barrington Public Theater Annual Benefit
Organization: Great Barrington Public Theater
Date: Friday, June 7th at 6pm
Location: Daniel Arts Center, Bard College at Simon’s Rock, 84 Alford Rd. Great Barrington, MA 01230
Berkshire Museum Gala
Organization: Berkshire Museum
Date: Saturday, June 15, 2024
Kids 4 Harmony Gala
Organization: 18 Degrees
Date: June 25, 2024 at 5:30 PM
Location: Tanglewood
Berkshire Music School 2024 Gala with Flutist Brandon Patrick George
Organization: Berkshire Music School and Ventfort Hall
Date: June 1, 2024 at 3pm
Location: Ventfort Hall
Museum Gone MAD Bash
Organization: Norman Rockwell Museum
Date: Saturday, June 8, 2024
Spring Fest
Organization: Walking Our Talk
Date: June 21, 5-8pm
Location: The Guthrie Center, VanDusenville Rd., Great Barrington
Gould Farm 5K
Organization: Gould Farm
Date: Sunday, June 2nd (or Virtual) – Check-in/Registration beginning @ 8AM. Combined Start Time @ 9:30AM
Location: 54 Gould Road, Monterey, MA (or Virtual)
Beacon of Hope: A Benefit for BIC
Organization: Berkshire Immigrant Center
Date: Sunday, June 9, 2024, 5pm
Location:Shakespeare & Company’s Tina Packer Playhouse
Season Opening Gala
Organization: Jacob’s Pillow
Date: Saturday, June 22, 2024
Berkshire Opera Festival Annual Gala
Organization: Berkshire Opera
Date: Sunday, June 30, 2024 at The Lenox Club
July 2024
Summer Gala
Organization: The Mount Edith Wharton’s Home
Date: July 7, 2024
Location: The Mount
Volunteers in Medicine Berkshires 20th Anniversary
Organization: Volunteers in Medicine Berkshires
Date: July 25th, 6 to 10 pm
Location: Cottage Farm of the Berkshires
Fete Des Fleurs: 90th Anniversary Founder’s Gala
Organization: Berkshire Botanical Garden
Date: Saturday, July 27, 6:00-11:00PM
Location: Berkshire Botanical Garden
ViM’s 20th Birthday Gala
Organization: ViM Berkshires
Date: Thursday, July 25 at 6:00
Location: Cottage Farm of the Berkshires
August 2024
Annual Gala
Organization: Mahaiwe Performing Arts Center
Date: Thursday, August 1, 2024 from 5-10pm – Show at 8pm; Gala reception and dinner start earlier
Location: Mahaiwe Performing Arts Center
WAM Theatre’s 15th Anniversary Benefit & Site-Specific Performance of Outside
Organization: WAM Theatre
Date: Sunday, August 18th
Location: The Mount, Lenox MA
6th Annual Art of Brewing Festival
Organization: Norman Rockwell Museum
Date: Saturday, August 10, 2024
Dinner, Democracy, and Dancing
Organization: Greenagers
Date: August 15, 2024
Location: 62 Undermountain Rd, South Egremont, MA
September 2024
BIFF Gala
Organization: Berkshire International Film Festival
Date: Sunday, September 1, 2024 4pm to 8pm
Location: Private Estate in West Stockbridge
BCAC Gala
Organization: Berkshire Community Action Council
Date: 9/23/2024
Location: The Mount, Lenox
Campaign Kickoff Breakfast
Organization: Berkshire United Way
Date: 9/12/24, 8:00-9:30 am
Location: Country Club of Pittsfield, 639 South Street, Pittsfield
LitNet’s A Celebration of Friends, honoring John Toole
Organization: Literacy Network
Date: September 20, 6:00 pm
Location: Amici Restaurant, West Stockbridge, MA
Celebrate the Berkshires
Organization: 1Berkshire
Date: September 19, 2024, 5-9 pm
Location: Pittsfield Municipal Airport, Pittsfield, MA
Berkshire HorseWorks 10th Anniversary Gala, Rescues On The Runway: A Walk Of Resiliency
Organization: Berkshire HorseWorks
Date: Friday, September 20th, 2024 from 6-9pm
Location: HomeFarm at Undermountain (400 Under Mountain Road Lenox, MA 01240)
October 2024
Celebrate Smitty!
Organization: Lenox Library Association
Date: October 9, 2024, 5PM
Location: Linde Center for Music and Learning
United at the Table
Organization: Berkshire United Way
Date: 10/30/2024, 5:30 pm
Location: Gedney Farm, 34 Hartsville-New Marlborough Rd, New Marlborough, MA 01230
Toasting & Tasting for Berkshire South
Organization: Berkshire South Regional Community Center
Date: October 19, 2024
Location: Berkshire South Regional Community Center
BFAIR 30th Anniversary Celebration
Organization: BFAIR
Date: October 25th, 2024, 4:30 – 8:30 PM
Location: Williams Inn
Gala Events 2023
January – February
NAACP Freedom Fund Awards (Virtual)
Organization: NAACP, Berkshire County Branch
Date: Saturday, January 21, 2023
March
Warm Up the Winter: Fuel Crisis 2023 Benefit Concert
Organization: Construct, Inc.
Date: Thursday, March 2, 2023
Sourdough Bread Baking Contest
Organization: Dewey Memorial Hall
Date: Friday, March 3, 2023
Show Your Teen Spirit
Organization: ROOTS Teen Center
Date: Saturday, March 11, 2023
19th Annual Robert “Bees” Prendergast St. Patrick’s Reception
Organization: Hillcrest Educational Centers
Date: Thursday, March 16, 2023
Stay at Home & Read a Book Ball
Organization: Lenox Library Association
Date: Saturday, March 25, 2023
Community Conversation on Poverty
Organization: Berkshire Community Action Council, Inc.
Date: Friday, March 31, 2023
April
Metallic Couture Disco Annual Benefit
Organization: Berkshire Art Center (formerly IS183 Art School)
Date: Saturday, April 1, 2023
Get BART Smart! Trivia Night & Fundraiser
Organization: Berkshire Arts & Technology (BART) Charter Public School
Date: Saturday, April 1, 2023
Benefit Performance: Tony n’ Tina’s Wedding
Organization: Berkshire Music School
Date: Saturday, April 29, 2023
May
The Focus is our Children Masquerade Fundraiser
Organization: Focus is our Children
Date: Saturday, May 6, 2023
CATA’s Annual Gala & Performance
Organization: Community Access to the Arts
Date: Saturday, May 13, 2023
Culinary Arts Dinner
Organization: Railroad Street Youth Project (RSYP)
Date: Saturday, May 20, 2023
June
Café Society: A Celebration of Puccini’s La Bohème
Organization: Berkshire Opera Festival
Date: Sunday, June 11, 2023
50 Years of Hevreh Celebration
Organization: Hevreh of Southern Berkshire
Date: Thursday, June 22, 2023 at 6pm
Season Opening Gala
Organization: Jacob’s Pillow
Date: Saturday, June 24, 2023
Season Opening Gala
Organization: Jacob’s Pillow
Date: Saturday, June 24, 2023
30th Lecture Series Celebration
Organization: The Mount, Edith Wharton’s Home
Date: Friday, June 30, 2023
July
Summer Celebration at Tanglewood
Organization: Boston Symphony Orchestra
Date: Friday, July 14, 2023
Flying Cloud’s Smarty Party
Organization: Flying Cloud Institute
Date: Monday, July 24, 2023
August
Becket Bash, A fundraiser for Becket Arts Center.
Organization: Becket Arts Center
Date: Sunday, August 27, 2023
Berkshire South Fundraising Event
Organization: Berkshire South Regional Community Center
Date: Tuesday, August 29, 2023
SEPTEMBER
Annual Fundraiser Celebration (title TBA)
Organization: Literacy Network of South Berkshire
Date: Saturday, September 9, 2023
Fourteenth Annual MS Awareness Fundraiser: Living Well Moving Forward Finding a Cure for MS
Organization: MS Support Foundation
Date: Friday, September 22, 2023
October
Tamarack Hollow 14th Annual Berkshire Drum Fest
Organization: Tamarack Hollow Nature and Cultural Center
Date: Saturday, October 14, 2023
Community Celebration
Organization: Berkshire South Regional Community Center
Date: Saturday, October 14, 2023