Photo above by Cherylynn Tsushima
JUNE
4 — BFAIR in Bloom
Proprietor’s Lodge, Pittsfield
This garden party-themed evening will feature beer, wine, and spirits from local vendors, thoughtfully selected food, music, and more to provide opportunities for people with disabilities.
bfair.org
5–7 — BerkChique
Ventfort Hall, Lenox
Explore a treasure trove of curated fashions and unique finds at this pop-up boutique supporting local nonprofits. Friday night’s First Dibs Party gets you priority access and complimentary refreshments.
berkchique.org
6 — Norman Rockwell Museum Gala
Norman Rockwell Museum, Stockbridge
The museum celebrates the opening of the exhibit “American Stories: From Revolution to Rockwell,” and honors the Museum’s long-serving director, Laurie Norton Moffatt, upon her retirement.
nrm.org
13 — A Novel Night Out
Belvedere, Lenox
The Lenox Library Association gala, celebrating the power and joy of community, invites you to eat, drink, and be literary with New York Times best-selling author and food personality Dan Pelosi.
lenoxlib.org
20 — Jacob’s Pillow Season Opening Gala
Jacob’s Pillow, Becket
The Pillow’s season opens with one-night-only performances and the presentation of the 2026 Jacob’s Pillow Dance Award, followed by dinner and dancing.
jacobspillow.org
23 — 18 Degrees’ Kids 4 Harmony Gala
Seiji Ozawa Hall, Tanglewood, Lenox
Internationally acclaimed pianist and composer Ted Rosenthal, winner of the prestigious Thelonious Monk International Jazz Piano Competition, will return as the gala’s 2026 Guest Artist.
18degreesma.org
25 — The Mount Gala: Observation Inspiring Art
The Mount, Lenox
Celebrate Edith Wharton’s masterful observation of human behavior with cocktails in the Italian Garden, followed by dinner in the mansion’s forecourt, where guests will be treated to a conversation with André Bernard and Roz Chast.
edithwharton.org
26 — Shakespeare & Company Gala
Shakespeare & Company, Lenox
Enjoy cocktails and hors d’oeuvres under the Tina Packer Playhouse tents, followed by a performance inside. A seated dinner from Peter Platt of The Old Inn on the Green and dancing round out the evening.
shakespeare.org
28 — Berkshire Opera Festival: Arias & Aperitifs
Gedney Farm, New Marlborough
Wine and dine while enjoying pop-up performances from Maestro Brian Garman and guest artist Stephan Egerstrom as BOF raises funds for its 2026 mainstage production of Donizetti’s “Lucia di Lammermoor.”
berkshireoperafestival.org
JULY
10 — BSO Summer Celebration
Tanglewood, Lenox
Celebrate the Boston Symphony Orchestra in its summer home with cocktails, dinner, and a performance of excerpts from “Swan Lake” led by Andris Nelsons and featuring pianist Seong-Jin Cho and the Boston Ballet.
bso.org/support/galas-and-flagship-events
11 — Fête De Fleurs: Garden Disco
Berkshire Botanical Garden, Stockbridge
Berkshire Botanical Garden invites you to don your fanciest hat to enjoy groovy music and scrumptious food in the shimmering evening gardens.
berkshirebotanical.org/fete
11 — PS21 Gala
PS21, Chatham, NY
PS21 honors Lael Locke with the 2026 PS21 Polestar Award in an evening that includes cocktails in the meadow, a farm-to-table dinner in the Pavilion Theater, performances from guest artists, and more.
ps21chatham.org
18 — Chesterwood Garden Tea Party
Chesterwood, Stockbridge
Enjoy tea, cocktails, live entertainment, and delicacies to taste on the former property of famed sculptor Daniel Chester French.
chesterwood.org
22 — Fairview Hospital Garden Gala
Gedney Farm, New Marlborough
This year’s event honors Carrie Herrington for her service to Fairview and the greater community.
berkshirehealthsystems.org
25 — The Trustees’ Garden Party
Naumkeag, Stockbridge
Experience the magic of Naumkeag’s gardens while enjoying seasonal cocktails, hors d’oeuvres, and live entertainment in support of the stewardship and programming at all Berkshire region Trustees properties.
thetrustees.org
26 — BSC Gala 2026: A Singular Sensation
The Stationery Factory, Dalton
Barrington Stage Company honors actress Debra Jo Rupp and celebrates the memory of supporter Reba Evenchik while raising funds for its education programs.
barringtonstageco.org
27 — Dreamers & Magic Makers Summer Soirée
Doctor Sax House, Lenox
WAM Theatre’s chic, brunch-style gathering celebrates women who inspire and create change. Enjoy seasonal bites, signature cocktails, music, and performances.
wamtheatre.com
AUGUST
1 — Hancock Village Summer Gala
Hancock Shaker Village, Pittsfield
Enjoy a magical evening where rolling hills meet a stunning sunset, and cocktails and music in the garden are followed by dinner and a night full of stars.
hancockshakervillage.org
1 — Olga Dunn Dance Company 50th Anniversary
Saint James Place, Great Barrington
Enjoy a very special performance celebrating the South County company’s 50th anniversary year.
olgadunndance.org
2 — Mahaiwe Performing Arts Center Gala
Mahaiwe, Great Barrington
The Mahaiwe honors its former board chair, Margaret Deutsch, with a reception and dinner, followed by a performance from Grammy-winning countertenor Anthony Roth Costanzo.
mahaiwe.org
8 — Bidwell House Museum Gala
Private home, Richmond
A stunning view, live classical music, and bites from Handcrafted Catering play into this year’s party theme: “the Berkshire Hills are alive with the sound of music.”
bidwellhousemuseum.org
Keep an eye on these organizations’ websites for more information on these late summer and fall events:
Berkshire International Film Festival Gala
Sunday, Sept. 6 | biffma.org
Berkshire Bounty 10th Anniversary
Thursday, Sept. 10 | berkshirebounty.org
Pittsfield Community Food Pantry Gala
Saturday, Sept. 19 | southcommunityfoodpantry.org
Berkshire Grown Gala
Thursday, Oct. 1 | berkshiregrown.org
Berkshire South: Toasting & Tasting
Saturday, Oct. 3 | berkshiresouth.org
LitNet Gala
Saturday, Oct. 3 | litnetsb.org/event
