A WINSLOW ESTATE WEDDING ON CAPE COD IN ORLEANS, MA

Gabby and Chris came to me just a few months before their wedding day. They had originally planned a large wedding at an indoor venue in Connecticut, but the pandemic hit and COVID-19 had other plans. Rather than postpone their wedding to a later date, they decided to move it to an estate on Cape Cod and make it an intimate weekend affair with a small guest count.  The Winslow Estate in Orleans, MA is a stunning waterfront property located in Pleasant Bay, and I was excited to help Gabby and Chris with their Plan B to get them married in 2020!

Because their original venue was in Connecticut, most of their original vendors made the hike out to the Cape to spend the day with us, which was warm and sunny for mid-October! 

As Gabby and her bridesmaids got ready, their photographer, Daphne + Dean, got to work capturing the details of the day, like this gorgeous invitation suite by Minted Weddings which featured a watercolor of The Winslow Estate. 

Gabby’s champagne Sam Eidelman shoes echoed their gold wedding bands and her aquamarine bracelet matched the dusty blue tones in the invitations.

We just loved Gabby’s gorgeous wedding gown from Blush by Hayley Paige with its nude bodice, sequin scroll overlay, and tulle skirt. It matched her naturally glamorous makeup by Sabi Makeup Artistry and romantic curls by Allure Traveling Beauty.

With her hair crowned with a beautiful floral headpiece by In Bloom Event Design, she was helped into her gown by her mom, a sweet moment to remember between mother and daughter. Then she made her way downstairs to reveal her final look to her bridesmaids. 

Her beautiful bouquet, also by In Bloom Event Design, featured anemone, eucalyptus greens and dahlias in corals and pinks. 

Before the ceremony, Gabby did a first look with her Dad who was brought to tears with how beautiful his little girl looked. We may have been a bit misty-eyed ourselves!

Meanwhile, the guys got ready in the Bay House next door. Chris donned his Indochino three-piece suit. His jacket was embroidered with his name and the date of the wedding, making it a real keepsake.  His floral bow tie and fun socks added to the dapper look.

When Gabby walked down the aisle with her dad it was Chris’ first time seeing her on their wedding day and his smile could not have been bigger. He was absolutely in awe of his wife-to-be and we love seeing a groom react this way!

They said their vows beneath a hexagon arbor, adorned with floral pieces, showcasing  anemone, dahlias and eucalyptus greens, and a breathtaking view of Pleasant Bay just beyond the trees. A one-of-a-kind view for a one-of-a-kind private estate venue!

With the bridesmaids in flowing sage gowns by Birdy Grey, and the groomsmen in navy blue suits, also by Indochino, Gabby + Chris’ wedding party looked picture perfect as they posed for celebratory photos. 

The October sunset over Pleasant Bay made for a beautiful backdrop as Gabby + Chris shared a romantic moment alone on the Winslow Estate’s private sandy beach, their first as husband and wife. 

Gabby + Chris entered the reception to a round of applause before making their way onto a special little patch of grass in the tent for their first dance, played by Chris’ Best Man, on the ukulele. 

Placed at the sweetheart table was a mini Rolls Royce toy car, an heirloom from Gabby’s family. 

After guests enjoyed the lobster bake from Clambakes, Etc., Gabby + Chris cut their two-tier wedding cake, covered in fresh flowers and a vintage bride and groom cake topper. 

Gabby shared a sweet dance with her father, before Chris and his mother took to the floor. 

Getting married safely during a pandemic is not for the faint of heart. Gabby and Chris’ day morphed into something completely different than they had originally planned. Between COVID guest testing, weather, tented wedding logistics, moving guests from location A to B, and much more - they stayed positive throughout the entirety of the transition and their weekend was one they (and we!) will never forget. 

Congrats, Gabby + Chris! We were honored to be a part of such a special celebration.

Wedding Planning + Coordination: Jessica Hennessey Weddings
Photography: Daphne & Dean
Floral Design: In Bloom Event Design
Entertainment: Power Station Events
Catering: Clambakes Etc.
Makeup: Sabi Makeup Artistry
Hair: Allure Traveling Beauty
Livestream Video: Cr8tive Light
Wedding Gown: Blush by Hayley Paige
Bridal Shop: Bella Bridal Shoppe
Bridesmaids Gowns: Birdy Grey
Menswear: Indochino
Stationery: Minted Weddings
Engagement Ring: Brilliant Earth
Wedding Band: Melanie Casey Jewelry
Wedding Cake: Veronica’s Sweetcakes
Wedding Cupcakes: Delicious Desserts
Venue: Winslow Estate