Holiday Entertaining Tips from Winsor Alums

November 14, 2023—It was a busy fall for Winsor alums in the Boston area. Cheering on the Wildcats at on-campus events like Under the Lights, gathering at the Winsor-Belmont Hill Boathouse for Head of the Charles, and attending author events like The Exceptions: Nancy Hopkins, MIT, and the Fight for Women in Science in the David E. and Stacey L. Goel Theater, there were ample opportunities to connect with old classmates and the larger Winsor community.

Ahead of the most wonderful time of the year, and building on the success of last year's event, “Sip, Style, and Snack” brought alums together at Winsor. With alums and staff instructors offering expert advice, attendees gathered in the Winsor Dining Room to mingle and learn tricks of the trade. Wandering between five different stations, alums put their taste buds, penmanship, and design chops to work. 

South End wine store Urban Grape, owned by TJ and Hadley Douglas '92, came to campus laden with bottles and suggested a mix of red and white wines perfect for holiday entertaining. A perennial fixture of the alumnae event calendar, the annual wine tasting at Urban Grape is scheduled for April 17, 2024. 

Using runners, tablecloths, flowers, and candles, Elizabeth Flint Hooker '95, owner of Dibby Flint Design, created a dramatic sample tablescape. A Boston-based interior designer and member of the Winsor Alumnae Board, she also taught four different napkin folds—including one shaped like a bow.

Formaggio Kitchen in Cambridge sent a cheesemonger for the occasion. Alums sampled cheeses and experienced different pairings with honey and jam. They heard about one of the latest trends in hospitality—creating a grazing board, and even learned to create their own salami flower.

Director of Engagement and Events Becky Withiam has 17 years in the event industry. When professional flowers just aren’t in the budget or when an arrangement wilts, she likes to have bud vases in her toolkit. Using fall blooms found at neighborhood grocery stores, she taught alums how to turn easy-to-find flowers like roses, tulips, hydrangea, sunflowers, greenery, and baby’s breath into a pop of color to dress up a table or a cheese buffet—and alums got to take home their creations.

However, it was the gratitude table where alums spent most of the evening, writing notes to the current seniors, the Class of 2024. With a big stack of blank cards and a checklist of 67 seniors, alums took turns writing multiple cards where they penned words of inspiration, advice, and encouragement. Some albums even stayed late to finish, wanting to make sure every single senior received an envelope. At the very next senior homeroom, cards were distributed to every member of the senior class.

Alumnae events often extend beyond Pilgrim Road. Also this fall, far-flung graduates heard from President and CEO of the Boston Red Sox and Chief Executive of Fenway Sports Management Sam Kennedy P’23 as part of a webinar and the annual Winsor/Belmont Hill Speaker Series. Additionally, alums met up in New York City, the first stop on the “Beyond Boston” tour that may be coming soon to a city near you.