A Year-In-Review: 24 Maine Engagement Sessions

In the last twelve months, I met up with twenty-four couples to create their Maine engagement portraits (two of which were also surprise proposals!).

I’ve met couples along the rocky shores of Acadia National Park, in the farmlands of Brownville, on Maine’s more southern beaches, in a coastal cottage in Harpswell, in wooded forests, and on the streets of Portland’s Old Port.

My couples came ready to play this season. They baked pies, dressed like pirates, ate pizza on sidewalks of Portland’s East Bayside, set-up board games, hit the local arcade, danced in the streets, blew bubbles, lit sparklers, and sprayed bottles and bottles of prosecco.

I made myself choose only ONE photograph from each session this year…and it’s was hard. (Hover over/click on each photo to get a description of the session!)

Brandon and Cecily drove up from Kentucky (that’s right - all the way from Kentucky!) for their engagement session (and also because Brandon’s name was picked for Maine’s moose hunting lottery).

Brandon’s cousin lives in Brownville, Maine and he opened his farmland up to us for their engagement session.

This shot was taken in the doorway of the chicken coop!

I met Ashley at a wedding show in November 2022 where she won a free engagement shoot! Though she and Justin Kyle currently live out-of-state, they visit Maine often and knew that they wanted Portland to be their backdrop. During their session we grabbed lobster rolls from Highroller Lobster Co. (if you visit Portland, it’s a MUST) and then we hitched a ride on the ferry to Peak’s Island for sunset photos.

Catie and Ethan had such a sweet and gentle session in downtown Portland. We walked around the Old Port and down to the wharf. We ended our session near Two Lights State Park in Cape Elizabeth, Maine just as the sun was beginning to set.

I’m sad to say that this perfect bubble gum pink wall has since been painted black.

When I first met Tina and Randy at Coffee By Design they had already booked their wedding with me, but they made the trip to Maine to meet some of their vendors. I loved them immediately.

They asked if I could meet them the week of their wedding, when they were back in Maine from Maryland, for an Acadia engagement session. Duh, yes. We must’ve traveled around the national park for about four hours. The only weather we didn’t see that day was snow, truly.

I am pro-doing an engagement shoot the week of a couple’s wedding. There’s so much anticipation and excitement that beams from the couple, and it gives them some time for relaxation and fun before what can sometimes feel like chaos during those last days before the wedding.

It was tough landing on a picture from Rob and Phoebe’s September session in Harpswell, Maine. We started our time together with them baking pies (Rob proposed to Phoebe with a pie that read ‘Marry Me?’ - I know, right?!). Ultimately though, I had to go with this picture. I love their embrace under this dramatic coastal sky.

Jen and Nic had a sweet engagement session along the trails of Pleasant Hill Preserve in Scaborough and Mackwork Island in Falmouth. I’m a sucker for a black and white photograph and I just love all the little details and intimacy of this particular shot.

Jeri and Megan wanted their backdrop to be Spring Point Ledge Lighthouse (which is just out of frame in this shot). They let me curate a small picnic for them, complete with a blanket, basket, wine glasses and a bottle of red wine (after their session kicked off with Jeri spraying a bottle of prosecco). If you haven’t been to the Southern Maine Community College campus, you absolutely should. It really is a gem.

Katie and Rob are so much freaking fun to work with! For their engagement shoot, they asked if we could take pictures at their favorite bar in Portland, Novare Res. I’m probably going to get this wrong, but I’ll try anyway: Novare has a huge selection of beer and cider. If you try them all (which takes a long time and is a real commitment), you get a fancy chalice/goblet situation. I bet by now Katie and Rob have finished the list - they had been whittling it down for sometime when we first connected.

After Novare, we headed to the East End where Katie and Rob walked around, enjoyed Fort Sumner Park, and ended our time together in field of lupins (which may have come with a latched tick - ugh!).

Stephanie and Justin giggling in front of one of my favorite murals in Portland. They are probably two of the kindest and most light-hearted people I’ve worked with. Have you ever met two people and just knew that they were right for each other? Yeah, that’s Justin and Stephanie.

It was impossibly hard to pick a shot from Katie and Cameron’s session. I mean, c’mon. They dressed like freaking pirates! Maybe you’re like, “Why did they dress up in costume?” I want to be the first to say the following: you NEVER need a reason to play. EVER. But this is how Katie and Cameron found themselves in costume for part of their session. When Katie told Cameron that they had their engagement shoot coming up, he said, “What’s the theme? What costumes are we wearing?” He was serious. And from there, it all fell into place. I made them a map of their relationship geography. I bought gold foil wrapped coins for booty and inflatable parrots for their arms. Cameron even put on a wig and pasted a fake mustache to his face! I’ll probably do a whole blog post on their session because it started with pizza in the streets and ended with games at Arcadia with pirate shenanigans in between.

Meet Gabby and Tyler, pictured here sitting on the grassy median on Fore Street in Portland, the U.S. Custom House positioned behind them. Moments before I took this picture, I ate shit on the cobblestones. Believe it or not, it wasn’t the uneven roadway that got me - it was my big toe getting caught in the opposite pant leg that took me down.

Maine meterologist Jessica Conley with her news journalist fiancé (now husband), Dustin Wlodkowski as they take in the sunset over Portland’s skyline from the East End. Jess is the reason I splurged on a pro-weather app to help my couples track their wedding day weather.

Sam kept Cassie (and me) laughing during our session last winter. Here they are on upper Exchange Street with Portland’s city hall as their backdrop. I also photographed these two enjoying gelato downtown at Gelato Fiasco where they shared their first date.

I met up with Dannyell and Jesse at Vaughn Woods in Hallowell, a location I used to shoot at all the time when I lived in Central Maine. There are no less than three photographers and their clients there at any given time, I swear. There are beautiful trails, stone bridges, and my personal favorite, the sprawling field Dannyell and Jesse are walking through in this photo.

Here’s a picture of Paul and Rachel smoochin’ in my favorite alleyway in Portland. For real - dig through my portfolio. You’ll see so many iterations of this alley which is located next to Blyth and Burrows (which isn’t Portland’s original hidden doorway bar - that would be Lincolns on Market Street, but it’s still a pretty great bar to check out if you’re in town). We also took pictures at The Francis, a stunning boutique hotel on Congress Street and at Henry’s Public House which is also in the Old Port.

Kristen and Alex drove up from Massachusetts for their engagement session. What I loved most about their pictures is that they incorporated something special to them into their photos. They fell in love over the game Terraforming Mars, so they brought it along with them. We set it up and I photographed them playing together.

This is the breakwater that leads out to Spring Point Ledge Lighthouse on the SMCC campus. It’s probably my least favorite place to shoot because the rocks are hazardous AF. It’s gorgeous and quintessential Maine, yes. But man, one wrong move and it’s lights out for me and my equipment. I agreed to this location because the bride-to-be pictured here is my sweet cousin Michaela, who is also a nurse. If you’re a nurse or a teacher, I’ll probably never say no to you. Shoutout to the breakwater in Rockland this is beautiful and not a hospital visit waiting to happen!

Tori and CJ came to Maine this summer for a coastal engagement shoot. First, we hit Kettle Cove in Cape Elizabeth where these two ran and jumped around on the beach. We ended our time together at Two Lights State Park, also in Cape Elizabeth. If you’ve never been to Maine, you should know there are forts, like actual historical forts and bunkers, all over the place. Two Lights State Park has one built into its hillside which is where I positioned Tori and CJ for this shot.

Katie and Tucker, who built a taphouse during the pandemic, tasked me with turning their syrup set-up into an engagement shoot backdrop. Done! We took pictures in the taphouse that Tucker literally built. They showed me how to make syrup and what the process looks like. We walked the property with their dog, Koda, and that’s where this shot was created. I love all of their pictures, but this one of their rambunctious boy does it for me.
You can see Katie’s engagement ring at the bottom of this post - hers is the one in the small tasting glass packed with snow.

Zeb and Elin had a sweet engagement session that started in the Old Port and ended at Kettle Cove. It was a wild day weather-wise. We started with gorgeous sunshine and ended in thick, chilly coastal fog. Not pictured here are their two sweet baby angel dogs who joined us at the end.

This shoot first started with Alec proposing to his girlfriend, Lindsey. I pretended to be a nature photographer (totally not in my wheelhouse) wandering around Winslow Park in Freeport. After Lindsey said yes, we took some more traditional style engagement pictures. I love how well the colors from the water and sky pair with Lindsey and Alec’s outfits.

Ranae and Matt basically kicked off my busy season in mid-April with their Belfast engagement shoot. These two have the biggest hearts and sweetest demeanours and I think that really comes through in their gallery. Ranae, who had recently lost her mom, requested that we take pictures on her birthday to honor her memory.

When I got Chris and Ernesto’s email telling me they wanted to book me for their wedding, I was so excited that I actually jumped up from my desk and ran around my house, hopping and dancing from room to room. I knew I wanted to work with these two from the minute our consultation started. Bonus: they’re tying the knot at the Barn at Walnut Hill, one of my bucket list venues!
Chris and Ernesto flew in from Texas for the Portland, Maine engagement photos. We started in Tommy’s Park and ended our session at Two Lights State Park in Cape Elizabeth at sunset. Chris even thought to bring Holy Donuts to use a props (check out the rings at the end of this post stacked up with some of Portland’s best donuts).

I think when you hope for a golden sunset, this is the one your visualize in your mind. This engagement session actually started as a proposal! Davis proposed to Chelsea right before golden hour at Kettle Cove in Cape Elizabeth. He had actually postponed proposing by a couple weeks because he really, really wanted the perfect sunset for their photos. And I think they got it! Chelsea’s friend, Megan, set up a lavish picnic of sushi and Veuve Clicquot.

Honorable mention goes to some of my favorite ring shots from these engagement sessions!

I can’t believe that my profession is documenting people’s love stories. As I write this entry, I can’t help but be flooded with gratitude for all the couples who put their trust in my art and storytelling, not just this past year, but for the last nine years.

I loved reminiscing on all of these shoots - there’s so much that I had forgotten about that started to come back as a typed up each summary.

Stay tuned for another post, but the next one will be my favorite shots from the THIRTY-ONE weddings and elopements I documented between April and October.

Thanks for keeping it real, gang.

-K