Shelby and Ryan's wedding at Cloisters Castle in Maryland

A family affair with lots of surprises and sentimental touches, Shelby’s and Ryan’s November wedding at Cloisters Castle in Timonium, Maryland, was no ordinary celebration. Their venue, was perched high on a hill among 60 acres of secluded woods, with architecture evoking medieval Europe. Intricately carved woodwork, stained glass windows that caught the light in jewel tones, and dramatic wrought iron details throughout, made the location feel cinematic. Designed by Sumner and Dudrea Parker to house their extraordinary collection of medieval artwork and artifacts, Cloisters Castle offers a sense of history and grandeur that few venues can rival. For Shelby and Ryan it was the ideal setting for a wedding day that blended romance, playfulness, heartfelt emotion, and more than a few unforgettable surprises.

Photographer Brittany Diliberto of Bee Two Sweet approached the day with her signature blend of thorough preparation and upbeat spontaneity. Known for building thoughtful, collaborative timelines for the couples she works with, Brittany worked closely with Shelby and Ryan to create a schedule that allowed them to enjoy their guests and let the day unfold naturally.

A Timeline Built for Easy Transitions

The morning began with Brittany arriving early to scout the castle’s grounds and interiors. With its dramatic staircases, hidden corners, and layers of architectural detail, Cloisters Castle rewards were evident to her as she explored it. By 11:00 a.m., photography officially began as Shelby and her bridesmaids prepared in one area of the castle, while Ryan and his groomsmen gathered in another.

Family members were honored and woven into the day from the very beginning. Shelby’s mom (our own Community Manager Sherry) and her grandmother joined the bridal suite, while both fathers and Ryan’s mom were present in the guys’ space. At 12:30 p.m., before either the bride or groom appeared, parents were invited to a quiet room at the top of the stairs to read heartfelt letters from Shelby and Ryan. Tears flowed freely. It was one of many moments that reinforced just how deeply this wedding centered around family connection.

By 1:00 p.m., both Shelby and Ryan were fully dressed, and Brittany moved seamlessly into solo portrait time. The moody interiors of Cloister Castle with its glowing stained glass created a dramatic backdrop for stunning award-worthy portraits. Using her twin Sony AI cameras paired with her beloved 85mm F1.4 and 50mm F1.2 lenses, Brittany captured photographs that call out to be framed and shared. 

Moving on from the photos session, Shelby shared a first look with her father, a moment filled with nostalgia and emotion. Then around 2:00 p.m., it was time for Shelby and Ryan’s first look.

Opting to see each other two hours before the ceremony allowed them to truly breathe and relax. They embraced, supported each other, and soaked in the meaning of the day. With time on their side, Brittany was able to take portraits of the couple with their two beautiful dogs and immediate family members along with epic wedding party images that leaned fully into the castle’s medieval charm.

Working with Shelby and Ryan who prioritized photographs of their family and friends, especially in a venue as visually rich as Cloisters Castle, was a dream scenario for Brittany. Portrait time never felt like an obligation, but more like a fun activity within the celebration.

A Castle Ceremony Full of Heart

At 4:00 p.m., guests gathered for the ceremony. The setting alone was pure magic, framed by the castle’s old-world architecture and the surrounding autumn woods. 

As the couple exchanged vows, the atmosphere was delightfully intimate yet regal. With two adorable dogs rounding out the wedding party and the sound of laughter filling the air, guests smiled and cried together.

When the happy couple were officially married, they took a few minutes to get an important portrait that was on their list.

A Staircase Portrait with a Twist

Shelby and Ryan had envisioned a portrait taken from above, with the two of them lying elegantly on the floor below Cloister Castle’s spiral staircase. Brittany, ever prepared, moved swiftly and efficiently to position them comfortably for the ultimate shot.

With her assistant lighting the couple and her second shooter, Pete Redel, supporting the effort, Brittany climbed the staircase to compose the photos. Once the frame was set, Pete sprinted upward with a bubble gun, filling the spiral with floating, iridescent magic.

As guests poked their heads in, curious about the source of the bubbles, laughter echoed through the stairwell. The image that resulted was nothing short of extraordinary, a perfect blend of technical execution and natural spontaneity.

“It was only possible through collaboration,” Brittany shares. “And most especially because of the sweet, comfortable connection between Shelby and Ryan.”

Surprises Around Every Corner

One of the central themes that made the day delightful was all of the surprises. Shelby purchased replica foam swords and medieval-style weapons to surprise Ryan and the wedding party. They leaned fully into the castle theme during group portraits, wielding swords with mock-serious expressions that quickly dissolved into silliness and fun.

Before the ceremony, Shelby’s parents gifted the groom and groomsmen a hilariously cheeky ring toss game to break the tension and set a playful tone.

Shelby and Ryan also surprised their parents with emotional letters and Ryan surprised Shelby with a stunning pair of earrings after their first look. Then, during the reception, Shelby's sister Meg and her best friend and bridesmaid Susanna stunned the entire room with a surprise performance of “For Good” from Wicked during her toast. There wasn’t a dry eye in sight.

Each surprise was layered with meaning, humor, and love.

A Reception Full of Energy and Emotion

By 5:45 p.m., the reception was underway. Parents were announced first, followed by the wedding party, who made a legendary entrance with swords in hand. Finally, Shelby and Ryan were introduced to roaring applause.

Dinner was served family-style by Absolutely Perfect Catering, reinforcing the communal, intimate atmosphere. Toasts began during the first course, with Ryan’s brother delivering a heartfelt speech that had guests alternating between laughter and tears.

The couple shared their first dance after dinner, followed by father-daughter and mother-son dances that radiated connection and sincerity. Then the dance floor opened, and exploded!

Brittany shifted into full reception mode, relying on her Flashpoint lighting system to balance the castle’s ambient glow with dynamic, directional flash. With her mastery of lighting she maintained the authentic feel of the space while capturing the high energy on the dance floor.

The party was out of control in the best possible way. Guests danced like no one was watching and Shelby’s gown swirled dramatically under the lights. Both she and Ryan had the time of their lives and the castle walls echoed with celebration.

The couple did take a minute to cut their cake but the dancing never truly stopped.

A Private Last Dance and a Bubble-Filled Farewell

As the evening wound down, guests gathered outside to prepare for the grand exit. But before stepping out into a sea of sparkling bubbles, Shelby and Ryan shared one final private dance alone in the reception space.

It was a quiet exhale after a day filled with joy, surprises, and emotion. 

When the couple stepped outside to a tunnel of guests blowing bubbles into the night air it was a perfect wrap to a day they and their guests will always remember.

A Photographer Who Feels Like Family

Shelby and Ryan’s connection to Brittany began long before the wedding day. Ryan found Brittany’s work and knew instantly she was the right fit. He hired her to secretly photograph their proposal (while eight months pregnant), and when they saw the results they knew they had their wedding photographer.

From that moment on, Brittany became more than a vendor. She became a trusted collaborator.

Her robust planning process eased Shelby’s mind. Her artistic vision elevated every space within Cloisters Castle. Her ability to be “magically present at all the right times,” as Shelby describes, ensured no meaningful moment went undocumented.

When the final gallery was delivered, Shelby and Ryan found themselves loving every image. And they knew this wouldn’t be the last milestone Brittany would capture.

A Truly Unique Wedding 

Shelby and Ryan’s wedding at Cloisters Castle was everything that the couple and their family members hoped. Layered with surprise, filled with love, and elevated by thoughtful planning, the bliss they felt as the day came to a close was clear on their faces and on those of the ones they love.

To see more work from Brittany Diliberto at Bee Two Sweet, check out her website and WBWP gallery, and reach out to her for exceptional wedding photography.

Wedding Professionals

Venue: Cloisters Castle – @cloisterscastle
 Planner: 1423 Events (Alex Reilly) – @1423events
 Photographer: Bee Two Sweet – @beetwosweet
 Caterer: Absolutely Perfect Catering – @absolutelyperfectcatering
 Hair: NVS Bridal (Stylist: Skye) – @nvsbridal
 Florist: Willow Oak Flower and Herb Farm – @willowoakfarm
 DJ: DJ Craig Wood (Perpetual Sound) – @djcraigwood
 Dress Boutique: North Fork Bridal – @northforkbridal
 Dress Designer: Essense of Australia – @essenseofaustralia   
Makeup: Nicole Palermo (Happy Ever After)