Waterfront Wedding at Shelter Island’s Historic Rams Head Inn
So much of making great wedding photographs is really the connection between me and my clients and often that starts with how much couples are willing to share in their first email. For example when Tiffany & Josh emailed me they both gave little synopses of how they met that I just found so charming:
Tiffany: I approached dating statistically. Mathematically I calculated a near zero chance I would meet someone out and about in Manhattan who would be all the qualities I was looking for- straight, male, attracted to me, attractive to me, kind, intelligent, quirky, fun, ethical, educated, likes cats, likes books, accepts me. So I turned to eharmony to narrow down the dating pool. I planned to go on a minimum of 20 first dates to expand my dating horizons. I went on 2. Josh was number 2. He was my last first date.
Josh: I never was a fan of the traditional style of dating where you go out and meet someone. I felt like there were too many important factors being left up to chance. I liked the idea of eharmony and getting to look at a profile of traits that were important to me. I was on eharmony on-and-off for about two years and I decided to give it one more shot before looking at another avenue. I was looking for someone smart, attractive, with a good sense of humor. Someone who could hold a deep conversation and was into learning new things and constantly growing. Tiffany was in Manhattan and I was near Philadelphia, she wasn’t exactly nearby. We went on a date, one date that lasted 12 hours, 3 restaurants and one special goodnight kiss. I knew she was perfect. Their first date lasted twelve hours, three restaurants, and one perfect goodnight kiss. When it came time to plan their wedding, they wanted something that felt like a classic romantic comedy: intimate, elegant, and timeless.
They also shared: We want our wedding to feel like a classic romantic comedy, a timeless romance- an intimate, fun and elegant party in someone’s beautiful backyard.
Shelter Island was the perfect setting for their wedding. Just a five-minute ferry ride from the eastern tip of Long Island, the island feels like a slice of bygone Americana—peaceful, unhurried, and quietly beautiful. In summer, when the beach-going population swells, there's a gentle hum of activity, but it never loses its sense of escape. The Rams Head Inn sits on the water overlooking the bay, with sweeping lawns that feel like someone's beautiful private backyard. Which is exactly what Tiffany and Josh were hoping for.
The ceremony took place on the lawn with the bay as a backdrop. Tiffany walked down the aisle in a classic gown, Josh waiting with the kind of smile that comes from knowing you've found exactly the right person. The cocktail hour unfolded on the same lawn, guests mingling as the afternoon light softened over the water. There's something about Shelter Island weddings that feels removed from the rest of the world—like time slows down just enough to let you take it all in.
After dinner, the weather shifted and everyone moved inside for dancing and celebration. But that's the thing about intimate weddings in places like this—the venue doesn't matter as much as the people in it. Tiffany and Josh had created exactly what they wanted: a romantic, elegant gathering that felt like home.
About Rams Head Inn
Rams Head Inn is one of Shelter Island's most beloved waterfront venues. The historic inn offers both indoor and outdoor ceremony options, with a lawn that overlooks the bay and provides one of the most serene backdrops on Long Island. Couples are drawn to Rams Head for its intimacy, its classic New England charm, and the sense of getting married somewhere that feels both timeless and deeply personal. It's the kind of place where your wedding feels less like an event and more like a celebration among friends in the most beautiful backyard imaginable.
If you're planning a Shelter Island wedding and looking for a photographer who understands intimate, elegant celebrations, I'd love to hear from you.
About Shelter Island
Shelter Island sits between the North and South Forks of Long Island, accessible only by ferry—a five-minute crossing from either Greenport or North Haven. That short ferry ride is part of what makes the island feel so removed from everyday life. You leave the car behind on the mainland (or bring it along), and by the time you disembark, the pace has already shifted. The island has been a quiet haven since the 1600s, originally inhabited by the Manhanset tribe before becoming a Quaker settlement. Today it maintains that same sense of refuge, with historic homes, pristine beaches, and a commitment to preservation that's kept the island remarkably unchanged. There are no chain stores, no traffic lights, just tree-lined roads and a summer population that swells without ever feeling crowded. For couples planning a wedding, Shelter Island offers something increasingly rare: a place that feels genuinely apart, where guests arrive already in vacation mode and the celebration unfolds at island time.
