Jessica Hennessey Weddings is a full-service, award-winning luxury wedding planning & design company based in New England, nestled between the coastal romance of Cape Cod and the quaint, yet bustling, city of Boston.
From the picturesque landscapes of Massachusetts to the serene coasts of Maine, our passion knows no bounds. With an unwavering commitment to excellence, we specialize in crafting unforgettable moments that transcend geographical boundaries. Allow us to turn your dreams into reality, no matter where your love story takes you!
JESSICA
LEAD PLANNER + DESIGNER
With more than two decades of experience in the production and events industries, founder Jessica Hennessey blends an Emmy award-winning background with an instinctive eye for beauty, storytelling, and logistics. Her approach is grounded in the belief that great weddings feel like great stories: immersive, thoughtful, and full of meaningful details that reflect a couple’s personality.
Jessica brings meticulous attention to detail, masterful organization, and a calm, collaborative presence to every celebration. From tented private estate weddings on Cape Cod to elevated coastal events across Boston, Newport, and Maine, she is known for transforming venues into spaces that surprise and delight. Her work has been featured in BRIDES, Style Me Pretty, Wedding Chicks, Ruffled, Carats + Cake, Bride & Groom Magazine, Glamour + Grace, and more, and she was awarded Best Boston Wedding Planner by Boston Business Women, and Best of the South Shore three years in a row.
The heart of Jessica Hennessey Weddings lies in creating guest experiences that feel warm, intentional, and entirely bespoke. Jessica partners closely with couples to understand their style, priorities, and vision, then leads the full creative process. From vendor curation to detailed timelines to immersive design moments, ensuring the day flows seamlessly.
As a two-time Emmy award-winning producer, Jessica approaches each wedding with a cinematic mindset: crafting moments that feel beautifully orchestrated yet full of genuine emotion. She believes the best celebrations honor family, elevate tradition, and give every guest a memory worth holding onto.
Jessica Hennessey Weddings exists to tell love stories in a way that feels elevated, meaningful, and unmistakably you.
FUN FACTS: Jessica is ordained in the State of Massachusetts and can perform a wedding ceremony in a pinch. When she’s not planning weddings, you can find her searching for a new adventure with her husband and two kids.
HILLARY
ASSOCIATE PLANNER
Hillary is a key member of our on-site coordination team. From rehearsal to day-of setup, her hustle and attention to detail makes her a critical asset on wedding days.
CHRISSY
ASSOCIATE PLANNER + PRODUCTION COORDINATOR
Chrissy assists with all of our planning logistics behind the scenes and is a key member of our on-site coordination team. Her ability to procure the most challenging production tasks are a crucial part of our success.
KATELYN
CONTENT MANAGER
Katelyn is our rockstar content manager, aka, keeper of all-things-media to bring our distinguished work out into the world.