Portland, Maine Engagement Session | Brynn & Josh’s Winter Waterfront Love Story
December 13th, 2025
There’s something undeniably magical about an engagement session in Portland, Maine, especially when a couple is willing to brave the cold for photos that feel authentic, romantic, and full of personality. Brynn and Josh’s engagement session was exactly that—a winter evening spent exploring downtown Portland, the wharf, the iconic Portland Headlight, and even warming up with mulled wine at Novare Res.
A Chilly Day Filled with Warm Moments
From the start, Brynn and Josh admitted they were a little nervous and described themselves as an “awkward couple.” And honestly? That’s my favorite kind of session. Real people, real emotions, and no pressure to be anything but yourselves. Despite the cold coastal wind, they showed up ready to have fun—and that energy made all the difference.
We began at the Portland Harbor Hotel, where the classic architecture and city charm set the tone. As we wandered through downtown and along the wharf, Brynn and Josh slowly relaxed, laughing between shots and leaning into the moment. One of the highlights was ducking into Novare Res for a quick stop for mulled wine—an unplanned but perfect pause that added such a cozy, candid feel to their gallery.
From Nervous to Natural
One of the things I pride myself on as a photographer is guiding couples who feel awkward or unsure in front of the camera. Brynn and Josh didn’t need to know how to pose or where to stand—that’s my job. With gentle direction, movement-based prompts, and plenty of reassurance, their connection naturally came through. By the time we reached Portland Headlight, the nerves were gone, replaced by genuine smiles, laughter, and quiet, intimate moments overlooking the ocean.
Why Winter Engagement Sessions in Portland Are Worth It
Winter sessions may be cold, but they offer fewer crowds, dramatic coastal light, and a timeless New England feel. Brynn and Josh proved that if you’re willing to embrace the season (and maybe a warm drink break), you’ll walk away with images that feel uniquely you.
If you’re recently engaged and worried you’re “awkward” or "nervous" know that you’re exactly who these sessions are for.
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