BROOKE + MATT

The sun was shining on the coast of Cape Cod for Matt and Brooke’s wedding day. This gorgeous couple may hail from New York, but as Matt’s family has a home in Cotuit, their roots are firmly planted in Massachusetts. So it was only natural that they should marry at the Wianno Club in Osterville.

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MICHAELA + GREG

Post-college sweethearts, Michaela and Greg had been together for years before he popped the question. To say this is one of my favorite weddings that I’ve planned would probably be unfair. The bride is my sister after all! But in all honesty this seaside, boho, beauty of a celebration, held at the Bohlin in Newport, Rhode Island, is truly the stuff of a wedding planner’s dreams.

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GABBY + CHRIS

Gabby and Chris had originally planned a large wedding in Connecticut, but the pandemic hit and COVID-19 had other plans. Rather than postpone their wedding, 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 in Pleasant Bay, and I was excited to help Gabby and Chris with their Plan B to get them married in 2020!

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EMILY + JUSTIN

While many couples have postponed their weddings due to Covid-19, others are opting for romantic elopements or micro-weddings with just very close family and friends in attendance. But we believe that no matter how small the event, couples should have a special day to remember, and that includes engaging a wedding planner to make everything perfect.

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DANIELLE + NICK

Danielle and Nick are the definition of puppy love! These dog lovers met when they were 14 years old on Cape Cod. Though they only saw each other during summers, the two stayed friends until they inevitably fell in love. Four years after they started dating, Nick proposed on the same beach where they met, making Cape Cod the perfect place for them to say, “I do!”

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REBECCA + CHRIS

Rebecca and Chris are such a sweet love story. They both attended Tabor Academy and circled back together later in life. Planning with these two was a breeze, as Rebecca had such a beautiful vision for how she wanted their day to play out. A stunning, coastal backdrop in a classic, Sperry tent - with lavish tree installations and hanging chandeliers. A true beauty!

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EMI + JOSH

I started working with Emi + Josh back in the spring of 2018. They had just moved to North Carolina and gotten engaged. Knowing they wanted their wedding to be back in Josh’s home state of New Hampshire, we immediately got to work - touring a bunch of venues up north and choosing the most perfectly gorgeous lake setting at Lake Shore Village Resort in Weare, NH.

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MAX + TORI

Max and Tori were one of the most laid-back, relaxed couples we’ve ever worked with here at Jessica Hennessey Weddings. With a seaside wedding ceremony set to take place on Skaket Beach in Orleans, MA - Hurricane Dorian came howling in the night before. Watching the weather has become a huge part of my job on Cape Cod as a wedding planner.

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Jessica Hennessey
MAURA + JOHN

When I met Maura + John, they had just recently gotten engaged and wanted to plan a quick celebration with their closest family and friends. This was our first time at Brae Burn Country Club - it is quite a charming space! They set the date for November and their day could not have been more perfect.

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