One Look at This Chestertown Wedding and You’ll Want to Have a Tent Reception Too

This Eastern Shore weddings hits all the marks: waterfront views, preppy attire, and a big, beautiful tent. At Hadley Wilmerding and Gregory (Greg) Stigliano’s wedding at the bride’s family’s farm in Chestertown, all of this and more was captured by Hannah Hudson Photography.

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Both originally from Pennsylvania, it was a mutual friend from their childhoods that first introduced Hadley and Greg. They met at a weekend spent at that mutual friend’s family farm, and both were quickly charmed. Greg says he was “taken aback by her stunning beauty, but quickly found that she was easy to converse with and was impressed by her fun personality.” The week after they met, Greg was on a business trip near Boston, where Hadley was living at the time, so he drove to Boston to take her to dinner.

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They’d dated for three years—two of which were long distance between Boston and Philadelphia–when on a Friday afternoon in October, Greg came home early from work. He suggested to Hadley that they go for a run along the Schuylkill River in Philadelphia. They paused at the Azalea Garden by the Philadelphia Museum of Art, and it was in there that Greg asked Hadley to be his wife. They later learned that Hadley’s parents had gotten engaged on the same day, 44 years prior.

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For their September wedding, they planned a rustic celebration on Hadley’s family’s farm in Chestertown. The groom dressed in a preppy ensemble of Vineyard Vines pants paired with a Brooks Brothers blazer, while the bridesmaids wore sea foam green dresses that matched the ring bearers’ light green pants. Though a thunderstorm threatened during the outdoor ceremony, the downpour mercifully held off until after the guests had made it safely under the tent for the reception.


The reception was accented with a stunning floral chandelier that hung over the dance floor. After listening to the touching toasts and celebrating with a filled dance floor, each guest departed with a small container of Old Bay that’d been given a custom label with the bride and groom’s wedding date. The bride and groom then departed for happily ever after, with plans to honeymoon in the British Virgin Islands.


Venue: Bride’s family farm, Ash Point Farm | Photographer: Hannah Hudson Photography | Event Coordinator: Michele White, Flawless Events | Bride’s Gown: Ivy & Astor, Lovely Bride | Groom’s Attire: Vineyard Vine, Charles Tyrwhitt, Collared Greens, Brooks Brothers | Hair and Makeup Artist: Hair for a Special Affair | Florist: Nancy Saam Flowers | Caterers: Magnolia Caterers | Music/Entertainment: CTO Tribeca | Invitations: Argus Printing and Invitations | Tent: Eastern Shore Tents and Events | Calligraphy: Sandra K. Pew Calligraphy

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Associate Editor

Caroline Cunningham joined Washingtonian in 2014 after moving to the DC area from Cincinnati, where she interned and freelanced for Cincinnati Magazine and worked in content marketing. She currently resides in College Park.