Chocolate & Diamonds Affair

The Woodland Hills Foundation is proud to announce our Eleventh Annual Chocolate & Diamonds Affair, to be held on Saturday, February 8, 2020 at the Edgewood Country Club. The evening will include a formal dinner, a silent auction, a wine-pull and live music with over 200 attendees.
2020 Tickets
2020 Ticket Sales open October 3, 2019.
General Admission: $50
Woodland Hills School District Teachers: $40
Become a Sponsor
Each year, we raise much-needed funds to provide support for our programs and services. Your support means that we can continue to provide important services to our teachers, school administrators and students.
Please consider supporting this community asset by becoming a sponsor of the Eleventh Annual Chocolate and Diamonds Affair.
Most sponsorship package offers tickets, recognition on event materials and media coverage. You’ll also expose your business to our impressive network of donors and friends—all of whom have a vested interest in the strength and well-being of our schools, our children and our community.
Donate to Our Silent Auction
Our Silent auction has become a huge part of raising funds at the Chocolate and Diamonds Affair. Guests have enjoyed bidding on jewelry, trips, gift baskets and more. This is the perfect opportunity to expose your business to our network of supporters.  When you donate an item/items, you'll be featured on the website, in donor-specific social media posts and more.

2019 Chocolate & Diamonds

On Saturday, February 9, 2019, we held our Tenth Annual Chocolate and Diamonds Affair at the Edgewood Country Club.

Dr. Stephen Esper, Director of Perioperative Services at UPMC Department of Anesthesiology and Perioperative Medicine, and Woodland Hills Alum, served as the evening’s emcee.  Guests enjoyed a sit-down dinner, a Silent Auction with close to 100 prize packages up for bid, chocolates provided by Sarris Candies, and a chance to win the evening’s pièces de résistance, a diamond provided by William Penn Jewelers, a Chocolate and Diamonds supporter since 2013. Local band Teresa Hawthorne & Legacee provided the perfect smooth jazz background for the evening.

Nearly 200 attendees came to celebrate the impact of the Foundation over the past ten years and our commitment to the faculty, staff, and students in our district. We also honored Woodland Hills Alum Brandon Greene, who, along with past honorees, was presented with a plaque, which will be hung in the Woodland Hills High school Library as part of a “Wall of Honor.”

The evening was a culmination of the work done by the Foundation over the past year in support of the Woodland Hills School District.


Through the generosity of our donors these programs can continue to grow and reach more members of our school and community. Board President Steve Gough also announced that the Foundation has, for the first time ever, hired two part time employees in order to facilitate the Foundation’s work. Over the past ten years we have made great strides and if the success of the event on Saturday night is any indication, we will continue to do so well into the future.

Lock in your sponsorships for 2020 now! Space is limited.

For questions or additional information, please email Jennifer Trehar at

Alternate Histories

Barbara Amick

The Bachtell Family

Bella Christie and Lil Z's Boutique

Burgh Bits and Bites

Busy Hook Happy Heart

Carnegie Mellon University

Carnegie Museum

Children's Museum of Pittsburgh

City Theater

Anne Countouris

Dicks's Sporting goods

JR Diroll Photography

Mia Good/Metamorphosis Spa

Kimpton Hotel Monaco


Lex Home Tech

Love Place Photography

Mama Meatballs Pizzeria

Miranda Miller

Mint Salon and Gallery

Jay and Sherry Ott

PICT Classic Theatre

Pittsbugh Festival Opera

Pittsburgh Arts and Lecture

Pittsburgh Penguins

Pittsburgh Pirates

Pittsburgh Public Theater

Pittsburgh Steelers

Pittsburgh Symphony

Pittsburgh Zoo & Aquarium

Porter Tours

Johno Prascak

Promo West Live

Quantum Theater

Raina's Catering

Rivers Club

Sara Rodgers

Robert Rosswog, DMD

Ruth Chris Steakhouse


Seven Springs

Lily Silknetter Photographer

Highland's House/Michael Sirianni

Summers Tanning Salon

Tennis Village

The Priory

Barb and George Thompson

Top Golf

Sue Trainor

Mary Trigo

Urban Achievement

William Penn Jewelers and Watchmakers

Woodland Hills Athletics




United Way Contributor Choice ID

Woodland Hills Foundation #10660819

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Who we are


The Woodland Hills Foundation is an independent non-profit 501(c)3 dedicated to supporting the Woodland Hills School District and its communities by strengthening the educational experience of our children.  

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