PUPO ON PILLOW

Spend a week in Maine at an expansive, magical, one-of-a-kind retreat your group will never forget. This imposing summer home -High Head - in Brooklin, Maine is the pinnacle of luxury combined with ru

Join Wendy Whelan - Associate Artistic Director of New York City Ballet and Jacob's Pillow Trustee - for a dinner and bourbon tasting for six guests at the iconic Union Square Cafe. Wendy Whelan, a Lo

Ten tickets and exclusive use of a Boston Garden suite to watch the Celtics or the Bruins rock the rafters. Game on! Package includes full, in-suite bar and beverage service.

Jet set to the Bay Area and experience the best of San Francisco! Enjoy a luxurious, three-night stay at the Mansion on Sutter - the only 5-star High Victorian Mansion in San Francisco. While in town,

Ivory Coast-born cooking sensation Roze Traore's resume includes experiences at Eleven Madison Park, NoMad Hotel, as the caterer of the Guggenheim International Gala, and as the owner of La Fourchette

Just steps away from the Pillow's Main Path, this parking spot has got your name on it (literally) for the entire season!

A not-to-miss experience across the pond that includes two tickets to a Royal Ballet performance of your choice in the 2023-2024 season. During your time at the Royal Opera House in London, you'll be

The New York City Ballet's 75th Anniversary Season starts this September. Enjoy two tickets to a performance during each of the company's 2023-2024 seasons: Fall, Nutcracker, Winter, and Spring. For o

A signed, original artwork by Berkshire-local Jim Schantz. Pastel on Stonehenge paper, 2023. 10" x 13.5" artwork, 14" x 17.5" framed.

Fun! Delicious! Curated by our Season Opening Gala Committee, each of these bottles was hand-selected by a different committee member. And, they have good taste! Enjoy this wonderful assortment with s

Acclaimed artist, illustrator and designer, New Yorker Maira Kalman has been celebrating the extraordinary aspects of the everyday for more than thirty five years. "People just live their lives and th

Time to recharge! The Kripalu R&R experience - the signature retreat at this renowned wellness center - allows you the freedom to choose what you need while you're here. Maybe it's a full schedule of

Take home this collection of sterling silver, hand-crafted jewelry and incorporate these unique, striking pieces into your wardrobe! This vintage collection features turquoise, lapis, and other custom

The ultimate day at the ballet includes four orchestra tickets to see Pillow Trustee, School Alumnus, and Gala Co-Chair Calvin Royal III in an upcoming American Ballet Theatre performance AND a backst

Take a trip to The Clark for a guided tour of the permanent collection and lunch for four guests in the Clark's Cafe. The lucky winner will also enjoy four tickets to a Shakespeare & Company performan

Make the most of a weekend in the Berkshires with a relaxing night away at the Gateways Inn in Lenox, MA. Your one-night stay for two includes breakfast and a three-course dinner. During the day, ther

Xin Ying joined the Martha Graham Dance Company in 2011 and her heralded lead roles include Graham's "Cave of the Heart," "Chronicle," and "Diversion of Angels." As portrayed through this striking pho

Good Moo's! High Lawn Farm invites our lucky winner to sponsor a calf! Yes, you read that right...Name a newborn calf, bottle feed her, and visit her in their nursery until she is up to four months ol

"An unstoppable train, blowing right past the local stations where you might have a moment to wonder exactly you’re headed"(New York Times). Get ready to experience the magic of the Tony Award-

Who do you love? Do they deserve some pie? Aura from Berkshire Mountain Bakery will bake four of her epic fruit pies for the lucky winner - the perfect treat for your next summer BBQ, family reunion,

Located only 40 minutes from New York City and walking distance from the Hartsdale Metro North train station, Scarsdale Golf Club is a true "home away from home." Four guests can enjoy a round of golf

Premiered by the Martha Graham Dance Company in 2022, Hofesh Shechter's Cave is a raucous, transform-the-stage-into-a-club experience, as brought to life by this photograph by Christopher Jones. Limit

Take home this commanding snapshot of Jose Limon's Psalm, as recently reimagined for the company in 2023. Limited edition 25" x 18" print on archival paper, signed by the Limon Dance dancers and the p

For one night only, Chef Bryant Terry is taking over the Pillow Cafe for a dining experience as a part of the Pillow's "Legacies of the Black Berkshires: An Evening with David Levering Lewis." At 7:30