It’s 6:30 am on Assateague Island. The mist is just starting to clear over the dunes—the day is ripe with a feeling of new beginnings. People arrive with kites in various hues, holding them high above their heads in a line, making a tunnel of sorts near the shoreline, which serves as the processional for a couple, Rachel and Benjamin. They enjoy flying kites, and this gathering at dawn is their wedding ceremony. Photographer Tiffany Caldwell is there to capture the first moments as Rachel and Benjamin celebrate their new life together. In this case, the photos will reflect the joyous nature of the couple, their jovial approach to life.

Some people remember the dress…or what was on the menu…or if there was a band or a DJ…or who danced with whom. Tiffany Caldwell remembers the emotions that erupt in an instant, the special moments she freezes in time, forever defining the first day in the lives of newly married couples.

“I try to capture people’s personalities, and let them bring themselves to the camera. I’m a good observer—you have to know when something is going to happen,” Caldwell said, explaining her approach.

“People aren’t just paying for someone to take their picture, they really want an artist to portray a scene.”

Caldwell is the owner and chief photographer for her business, Tiffany Caldwell Photography, based in Rehoboth Beach, DE. Caldwell, along with associate Kyle Tenyck—a talented recent college graduate that Caldwell says, simply lives for his love of photography—also take engagement pictures, family beach pictures, and some studio sessions. But first and foremost, Caldwell specializes in weddings—her approach is to focus on doing one thing, and doing it really well.

Caldwell started off with an interest in photography as a high school student in Severna Park, MD. She bought her first Pentax K 1000 at a flea market and entered into a love that would beckon her again years later, after a similar career would end.

Caldwell attended college at Towson State. She studied Advanced Photography abroad in Florence, Italy for a semester, but a film class taken towards the end of college would act as the catalyst to graduate school at Chapman University in California, where she would go on to receive her MFA in film. Predictably, a career in the film industry followed, but it didn’t provide the kind of day-to-day conducive to the next phase in Caldwell’s life.

“It’s the kind of job that takes everything out of you, and at the time I had to grown to want some other things out of life,” reflected Caldwell.  

While expecting her son nearly nine years ago, Caldwell decided she needed to return to the east coast. By this point, her family had all migrated to the Eastern Shore—her parents to Fenwick Island. It was a decision that just seemed right even though it hadn’t been a part of her future plans, before.

“I grew up coming down in the summer, making money, and never imagined living here year round. It was a transition at first, but I couldn’t imagine living anywhere else, I love it,” said Caldwell.

Becoming a Photographer

Initially, Caldwell found her way back to the camera professionally speaking, by simply taking pictures of her kids. Then a college friend asked Caldwell to take pictures of her beach wedding.

“I thought at first maybe it was something I could do on the side, then I did it, and loved it, and so I tried to figure out how I could really make a go of it,” reflected Caldwell.

Living in Berlin, MD at the time, Caldwell began with local marketing, worked on building her portfolio, and created a website. A move to Rehoboth Beach opened up more opportunities and wedding venues; the business took off.

Indicating the artistry behind Caldwell’s approach, equally important to her love of taking photos, was the transition of the wedding photography industry as a whole.

“I’ve always been really into people, really into photojournalism—telling the stories. I love that aspect of it. After shooting my friend’s wedding, I noticed the business changing from those staged shots to the candid moments. It really happened at the right time for me,” explained Caldwell.

There’s a saying Caldwell uses to define her business philosophy and attitude…”altering your life by holding it still,” taken from a quote by Dorothea Lange. The first famous female photojournalist, Lange made a name for herself by capturing the faces of the Depression during the 1930’s. Caldwell has always admired Lange. Her inspirational photos depicting the undercurrent of emotion is the same philosophy Caldwell applies to her own work, albeit on admittedly lighter subjects.

Caldwell says she specializes in capturing everyday moments in their natural form. She looks for the emotion in an intimate moment, which is really how she defines the “perfect shot.”

“Technically you may get the perfect shot in terms of lighting or setting, but if people aren’t lose, or free, you won’t really capture them. It’s best when people forget I’m there,” Caldwell explained.

Forgetting the photographer seems to happen most easily in the often-stressful moments leading up to the wedding ceremony.

“My favorite shots are always the ‘getting ready’ shots. It’s those very intimate moments—a mother helping her daughter get ready—before they are on display. People are so caught up with what’s about to happen, they aren’t posing for the camera.”

The Ideal Scene

The Eastern Shore is home to a plethora of beautiful scenes—small historic towns providing potential backdrops for period movies, the miles of white sandy beaches acting as vacation paradise—a photographer’s playground. When prospective brides and grooms travel here for weddings, or are even from here, weddings tend to be more unique with the couples capitalizing on their surroundings.

“It’s great doing weddings here because if people are traveling for beach weddings, you know they aren’t going to be just traditional, they are going to be more open to other ideas,” said Caldwell.

“And there’s just so many great locations here. Either the privacy of nature, the energy of the boardwalk, or the vintage feel of the old towns,” Caldwell continued.

Some of Caldwell’s favorite spots to shoot photos are places locals pass through daily, live in, and perhaps even take for granted. But it all changes when you see the world through a photographer’s lens.

“I really like shooting downtown Ocean City—the pier and the boardwalk. I had a couple that wanted to do boardwalk shots, there were people everywhere and they became the backdrop. It was really fun, and had a nostalgic feel,” said Caldwell.

The opposite to the energy of the boardwalk and the summer crowds, is the relative calm and isolation found on deserted beaches, or in a nature preserve—both locations Caldwell uses regularly. She’s also a fan of the historic towns—chief among them Berlin, MD with the Atlantic Hotel, the breathtaking setting of Merry Sherwood Plantation just a few miles down the road, and the old houses and historical society of Lewes, DE. Nassau Valley Vineyards also in Lewes, is another favorite, which manages to convey an old world, off-the beaten path feel, so close to the commercial area of Route 1 and the bustle of the Rehoboth Boardwalk.

Caldwell shoots about 20 weddings a year, with couples booking anywhere from six months to a year in advance. Mainly weddings take place in the warmer months, but Caldwell says that too is changing, with more and more couples favoring the pleasant weather and smaller crowds that fall brings.

Although she loves shooting on the Eastern Shore, Caldwell is hoping to branch out to some of the neighboring cities like Philadelphia, Baltimore, and New York, just for a change of pace. She has recently teamed up with Bella Photography, a booking agency that facilitates more out-of-market opportunities. But ultimately, Caldwell’s heart lies with the Eastern Shore.

Taking into consideration all of her experience shooting on the shore, it begs the question, what does Caldwell remember most about the weddings she’s been a part of?

True to her heart as a storyteller, those that stick out most in Caldwell’s mind aren’t the most lavish, or the largest, they are the ones that brought forth the most personal reflections.

“I’ve done a bunch of weddings on private property. The yards are tented; everything is brought in and personalized. One family had a boat filled with ice and drinks and they were shucking oysters, another took my suggestion to leave their reception on a golf cart with cans hanging off the back,” remembered Caldwell.

It’s evident that Caldwell fondly remembers the personalities of her couples, the efforts made by them to convey their personal joys into their special day. And she is the storyteller who sees life’s little details through her lens, and captures those special moments, freezing the memories for all time. In her own words as to what truly motivates her work,

“I love people; I love people that are in love, and I’m really inspired by people that exemplify that.”

Find Tiffany Caldwell Photography on Facebook, or her website.

Side Project:

Caldwell has recently started a resource guide called Marry Me in DE in response to the passage of the law allowing same-sex couples to marry in Delaware. The guide brings couples in contact with gay-friendly vendors and establishments. Marry Me in DE is currently offering a free day of wedding photography to a couple who shares their story. Find more information here.

Read other Down the Aisle – Eastern Shore Style features:

All gallery photos by Tiffany Caldwell.