Glen Island Harbour Club: Two stormy weddings, one unforgettable venue

The harbor at Glen Island Harbour Club was wild on the last Saturday in October. Deep green waves rolled past the walkway outside the getting ready area, tall enough to almost crest above the railing, driven by a wind that had been building all night. On the other side of the floor to ceiling windows, I watched the storm gather strength as I photographed Lital’s details. I remember thinking we had two options: lean into the raw, wild weather to create something authentic and unfiltered, or play it safe.

Three months later, in January, I stood in the same prep room with Rebecca while snow fell fast, thick, and sideways, accumulating fast. I had finished photographing her details, using the falling snow as a contrast to her flowers. She was ready to go outside and do her first look next to the water, despite the snow covered ground.

Both couples, in their own way, leaned into their day and embraced the weather, chaos, and beauty. Their photos were not standard or sanitized versions of a wedding album, but deeply personal and unique. In this post I’ll share more about their stories, why a Glen Island Harbour Club wedding in New Rochelle was the right choice for them even with the weather working against them, and how we handled the curveballs their days threw at us.

Photo by Matthew Rigby Photography

Getting ready

During October’s driving rain, Lital got ready in the prep room downstairs while Matt got ready upstairs. I incorporated the harbor views and the weather itself into their detail photography. The contrast between the intimate moments of getting ready and the raw energy happening beyond the glass documented the mood and feeling of the day. Despite the weather, their family was full of anticipation and joy, and the spaces were large enough to accommodate them and a full lunch spread without feeling cramped. The venue’s coordinators were present, attentive, and helpful the whole time, attending to every need and making sure everything flowed.

Rebecca got ready in the same space three months later, with snow coming down outside her window instead of rain. Matthew and his brothers got dressed in the room at the back rather than going upstairs, which gave them easy access to the back patio. My second photographer took him and his family outside for portraits in the cold, while I used the snow as an authentic element in Rebecca’s detail and prep photos.

Photos by Matthew Rigby Photography

First look and portraits

Lital and Matt

Lital and Matt had originally planned to do their first look outside, but the rain kept us from following through. Our rain plan, an idea I suggested based on the spaces available, was to move it inside instead. We tried the covered carport area in the back first, but the rain had come in underneath and would have gotten her dress wet. The venue’s wedding captain and I cleared a section of the lobby and lined up their friends and family along the wall for a front row seat to their first look. Lital’s mother was overjoyed, taking photos and cheering. Despite having to move indoors, it was an emotional, unplanned moment that kept the feeling they had originally envisioned.

From there, the coordinator brought us to the empty ballroom at the back of the venue, offered graciously as a second space to work in. Even indoors, the wedding party photos included the scenic view of the harbor through the floor to ceiling windows. I set up off-camera flash to balance the low light with the window light, while my second photographer helped organize the groupings so we could move quickly through both sides of the party.

Rebecca and Matt

Rebecca and Matt’s winter wedding was always planned to stay mostly indoors, but they were brave enough to venture outside for portraits. In the early afternoon they walked through the snow during a lull in the storm to do their first look outside on the back patio. They wanted the weather woven into their day, not hidden away. After the emotional first look, their wedding party and family were cheering through the windows while they went on to explore the spaces behind the venue. They climbed onto a rock formation overlooking the harbor, fresh snow blanketing it. They then walked around the corner to the outdoor seating area, which had gas firepits, and spent a few moments there while Rebecca reminisced about roasting marshmallows and making s’mores growing up. This tradition has become one of their favorite pastimes together in their new apartment. Warming back up inside, they talked about how much the moment felt like them.

Photos by Matthew Rigby Photography

Family photos

We used different areas of the venue for family photos with both couples, depending on what was happening. With Lital and Matt, we moved to the space where cocktail hour would be held, with its own view of the harbor from a different angle. With Rebecca and Matt, we used the carport area originally planned for Lital and Matt’s first look. The venue staff worked with us at every turn, setting up for cocktail hour while we photographed nearby.

Photos by Matthew Rigby Photography

Ceremony

Both ceremonies took place upstairs in the main room, with panoramic harbor views. During Lital and Matt’s ceremony, the rain pounded the windows hard enough to hear it. I set up flashes to balance the weak natural light coming through those windows with the motion and emotion at the chuppah. With flash the weather and landscape outside became part of the ceremony’s atmosphere, adding to the wedding story they will relive for years. Before the main ceremony, they held their Badeken downstairs on a small stage beside the cocktail area, while Matt’s Tish took place upstairs in one of the open rooms.

Rebecca and Matt signed their Ketubah in the area off the cocktail area, in a smaller ceremony with only family present before everyone else arrived. Their chuppah ceremony upstairs had a similar setup but a different feeling. The snow fell steadily but quietly while live musicians played the entrances. The light was dim and gray. Again, I used flash to document both the couple and the landscape behind them.

Photos by Matthew Rigby Photography

Evening portraits and reception

As the day moved into evening, the weather became part of the story in a different way.

Lital and Matt

We ventured outside in the late afternoon during a break in the storm. The sky was still heavy and dark, and it was still raining lightly. They held hands and braved the elements, taking in the moody view across the water. As we were heading back indoors, the rain stopped and an uncle ran outside yelling “Rainbow!” We ran back outside and they laughed, danced, and embraced under a double rainbow while I photographed them. It was a moment none of us had planned for, and none of us will forget.

At the end of the night, Lital and Matt went outside one more time, into the rain, for a creative night photo, which became one of my favorite portraits from the day.

Rebecca and Matt

Rebecca and Matt went outside to make creative night photos in the snow during their cocktail hour. They were so happy to be together, willing to explore and play in the landscape. We worked through the snow, set up off-camera flash through the pine trees, and documented them in the raw beauty of a winter night. These photos had a unique energy that felt true to them.

Photos by Matthew Rigby Photography

Reception

Rebecca and Matt had a live performance from electric violinists and worked in music that reflected their shared interest in Star Wars and The Lord of the Rings. Lital and Matt had a custom setup during their reception that had to be moved halfway through the first dance set. At both weddings, the staff at Glen Island worked efficiently and handled the weather changes with grace.

Photos by Matthew Rigby Photography

Working with the videographers

Both couples took my recommendations for videographers, and both brought a documentary sensibility that matched the rawness of these days. Fen’s longer-cut, eighties-inspired style let her blend into Lital and Matt’s day the way I try to blend into every wedding I photograph. She was present without being intrusive, documenting moments as they happened rather than staging them. Brandon and I worked as a tag team throughout Rebecca and Matt’s day, setting up details together and moving through the timeline in sync. Both collaborations felt natural, and both couples walked away with photography and films.

Vendor credits

Let’s talk about your wedding at Glen Island Harbour Club

Glen Island Harbour Club is a venue that helps you hold onto your wedding vision, even when the weather has other plans. Its spaces are generous, and the harbor itself, even on its stormiest days, is genuinely beautiful. If you’re planning a wedding there and wondering what happens when things don’t go as planned, I hope these two days give you some confidence. The best photos often come from the moments no one planned for.

If you’d like to talk about your Glen Island Harbour Club wedding, I’m easy to reach.