Blog Category: Engagements (Page 3)

Photographing a special proposal in Chilmark for Hilary and Lindsay

One of the best things about life as a photographer is being invited to share in a special moment between two people, and to be able to genuinely capture that lifelong memory for them. Earlier this year I had the opportunity of shooting a proposal between Hilary and Lindsay, a couple brought together by their love of Martha’s Vineyard, and whose family I have come to know in recent years.

In early August I received a brief email from Hilary’s mom Jill, asking if I was available on a particular date, with little details provided. I had previously worked with the family on a spectacular birthday celebration for Jill, and I was happy to take on any additional projects. I was later informed that my new assignment would be helping Hilary stage the perfect proposal for her girlfriend Lindsay, at a private Chilmark beach on the north shore overlooking Vineyard Sound. I was sworn to secrecy and delighted to play a part!

Soon I was with Jill and Hilary’s father, Alan, scouting the perfect beach location – a stretch of sand the couple had both, separately frequented as kids – the day before the big ask. Jill and Alan staged the proposal themselves, with Alan even getting down on one knee to mock the exact setting for Hilary –  it was a true family affair. The following day I returned for the real thing. While Hilary’s parents hid a celebratory picnic of oysters and champagne behind the big rock, I hid out of sight to photograph the proposal. The plan was for Hilary and Lindsay to arrive at 4pm, to ensure we captured a beautiful fall sunset after she popped the question.

I positioned myself far off in the dunes overlooking the rock where Hilary was planning to ask Lindsay. As I laid on my stomach, silently waiting for the perfect shot, I was reminded of my time as a Greenpeace photographer, aboard the Rainbow Warrior, covertly capturing a moment in time that told a much bigger story. There I was, sneaking in the sand, set to record an event that was so rich, and had so much meaning for these two women and their families.

Eventually Hilary and Lindsay emerged from the stairs leading to the beach and walked to the rock. Soon Hilary was confessing her love to Lindsay, down on one knee and presenting a ring, while I discreetly captured the whole thing from above. The happy couple savored the moment together and then summoned me to the shore, for some more shots of them basking in their newly engaged bliss. The day finished with a congratulatory dinner at State Road restaurant, where Lindsay was surprised yet again with her family and Hilary’s, and I was yet again there to capture it all. It was a magical day for us all,  and an experience I too was grateful for.

Creative proposals have become a very big trend (I shot six others just this year). More than that they mark the beginning of a new chapter in a couple’s life together and the forging of their families – not to mention a great story for the grandkids. Thank you to Hilary and Lindsay, as well as their families, for allowing me to share in their special memory.

You can read Hilary’s version of the events at

RANDI BAIRD PHOTOGRAPHY  |   508.696.5335   |

Keya & John’s Martha’s Vineyard Wedding

Wedding Details:

Couple: Keya & John’s Martha’s Vineyard Wedding
Ceremony: Harbor View Hotel
DJ: The Sultans of Swing
Wedding Cake: Val’s Cakes

This past spring Randi Baird Photography was honored to capture John and Keya’s engagement session on Lucy Vincent Beach in Chilmark. This summer they invited us photograph their wedding at the Harbor View Hotel in Edgartown!

John and Keya selected flower designer Kristina Collins from Tea Lane Farms for their floral arrangements and bouquets. They chose The Sultans of Swing for their live music, and Val’s Cakes for their clothing-inspired cupcake desserts.

The couple’s personal touches made the wedding exciting and memorable for their guests. They even designed their own wedding signs (pictured above).

Thank you, Keya and John, for allowing me to photograph your Martha’s Vineyard wedding!

Charlie + Ashley’s Engagement Session

Randi Baird Photography is based primarily in Martha’s Vineyard, but we love traveling! It’s such fun to explore different destinations and wedding traditions around the United States. We’ve visited Los Angeles, San Francisco, Boston, and several times a year we head to NY to shoot family portraits, engagements, and corporate work. This past fall we flew New York City to capture Charlie and Ashley’s engagement session!

The Engagement Session took place in and around Central Park on a windless, seventy-degree October day. Between the cloudless sky and the fall foliage- the location could not have been more perfect!

Charlie and Ashley plan to marry at Martha’s Vineyard Edgartown Yacht Club for their September 2017 wedding. They are sweet and easy going, and we can’t wait to photograph their wedding!

Auspicious Day for Keya + John at Lucky’s Lounge in Boston

Sometimes the stars align just right, and you just get lucky. For Keya and John, that moment came during the July 4th weekend of 2013, when they met by chance at a bar called Lucky’s Lounge in Boston’s Seaport District. Keya was coming off a really tough week, during which her basement flooded, and decided to call up some girlfriends for a fun night out. They were supposed to go to the Legal Harborside’s rooftop bar, but it was closed, so they reveled in drinks and dancing at Lucky’s instead.

John was there that night, and a gentleman he befriended that evening took an interest in Keya’s friend. Ever the loyal wingman, John made several attempts to talk to Keya while his new friend pursued her friend, and after finally meeting with success, John asked Keya out to dinner to Ming Tsai’s new restaurant, Blue Dragon.

Unfortunately, things did not work out quite so well for John’s friend. Both Keya and John left Lucky’s that evening believing that the other hailed from Latin America, even though Keya’s heritage is Indian and John’s family came to America on the Mayflower.

Thankfully, they were able to recognize each other a week later on their first date at Blue Dragon, and have been sharing their love of delightful restaurants and many other things for the past almost three years.

Keya and John live in Acton, Massachusetts with Keya’s (and now John’s) five-year-old daughter, and are eagerly anticipating their upcoming wedding in their favorite destination—Martha’s Vineyard.

Caitlin + Ross on Bluebird Farm

When Caitlin + Ross told me they were having Bluebird Farmer Krishana Collins grow, create and style their flowers for their upcoming May wedding I knew that would be a fabulous location for their engagement session. And even though there was frost on the ground that morning, the sun was out and the crisp air was invigorating.

Caitlin & Ross met in 2010 when they were living in NYC. They had both attended the University of Missouri (Mizzou), but had never met each other. Years later when they were dating, they discovered that their paths had crossed during a special event in Caitlin’s life, but had no idea! They were a charming couple, so in love, and looking forward to a Vineyard wedding in May. Both Caitlin and Ross spent their childhood summers on the island, and when deciding where to have their destination wedding, it was clear to them that having it on the island would be the perfect choice.