Bear and Pineapple Photography

Bear and Pineapple Photography Lifestyle photographer specializing in families + natural light portraits. Located in Cumberland, ME

quirky, imperfect, compassionate human spreading kind vibes, realness + all things love through my art

My first session of 2026 did not disappoint! I recently spent the morning with .art and learned a little about her proce...
02/20/2026

My first session of 2026 did not disappoint! I recently spent the morning with .art and learned a little about her process and art. The thing about working with other creatives is you have the luxury of saying “trust me” and they do! I’m sort of obsessed with my idea of Jenn looking through her art on plexiglass. If this is how all 2026 unfolds, it’s going to be a great year!

2025 is officially wrapped up - making it my 7th year in business!  I have a lot to say below, but before you read, plea...
12/14/2025

2025 is officially wrapped up - making it my 7th year in business! I have a lot to say below, but before you read, please enjoy this year's photos of me, courtesy of my daughter!

Admittedly, it was a challenging year overall. Business wasn't as steady and spread out as previous years. This left me squeezing in the majority of my shoots towards the end of the year - which left me completely, utterly exhausted and scrambling to find any kind of downtime with my family.

On top of that, life has gotten expensive. You all have felt it. Everything has increased, and that includes all things to run a business. When I sat down to crunch the numbers throughout the season, it was jarring. There have been many tearful conversations in my house of "does this make sense anymore"?

2025 also revealed something interesting: a majority of my clients opted to keep their images private. I will always honor this request. I do not treat your session ANY different, and you still receive the best of my abilities. But, on the flip side it makes it more challenging since I can't share my newest work. It's a sign a growing number of people are becoming more weary of social media. However, it's an added pressure on top of the ever changing agrithoms to even get yourself seen!

This was a rough year for many of us, and I'm going to use the calm and quiet of winter to brainstorm, recalibrate and learn what areas I can pivot.

Rest assured, there is nothing I love more than knowing images I took might end up in the hands of future generations. I'll never take it for granted. It's an absolute honor to even be trusted with such a beautiful opportunity.

While challenging, 2025 also had incredible moments and energy! We raised $1,112 for Maine Needs and the Locker Project + I had another photograph published in a magazine. But the best part? High fives and hugs from kiddos, genuine "thank you for making that fun and easy" from parents, and an abundance of gratitude from all my clients. I appreciate each and every one of you. From the bottom of my heart, thank you for all the support and love you give my business in whatever capacity you can!!

Here's to silly faces + 2026!!

One of the last shoots of my season was simply gorgeous!
11/23/2025

One of the last shoots of my season was simply gorgeous!

Cuteness overload 😍
11/20/2025

Cuteness overload 😍

My minis are QUICK, but if you bribe your children (😉) to be attentive for a short time- I promise we will get a handful...
11/18/2025

My minis are QUICK, but if you bribe your children (😉) to be attentive for a short time- I promise we will get a handful of cute images for those holiday cards!

Fun fact: one year when I photographed this sweet family I showed up to their house in the morning with my slippers and ...
11/17/2025

Fun fact: one year when I photographed this sweet family I showed up to their house in the morning with my slippers and without my camera. That was the first and last time that ever happened 😂 thankfully they found it amusing and I lived just around the corner so it was a quick fix- but a memory I will never forget. Appreciate all the years they have hung in there with me! My clients are the best 🤍

Strike a pose: twin edition.
11/16/2025

Strike a pose: twin edition.

I went on a side quest this fall and headed over to  to document morning chores! We started off with a beautiful sunrise...
11/12/2025

I went on a side quest this fall and headed over to to document morning chores! We started off with a beautiful sunrise which turned into the thickest blanket of fog about 15 minutes into the shoot. A true Maine weather experience. I spent 2 hours with the Sinisi’s and got to see just a small portion of what a day in the life is like. What I can say is this: they are some of the most down to earth humans, they work incredibly hard, and they treat their animals with respect and gratitude. They also have a super cool tiny house () - If you’re looking for your sign to get away from the noise of the world- here it is! It’s a relaxing getaway, and one I have frequent once a year. I am so appreciative to and for folding me into this special project!

Obsessed with this fam 🤩
11/10/2025

Obsessed with this fam 🤩

How lucky are we to live in Maine?
11/04/2025

How lucky are we to live in Maine?

This little dude gave me a workout and I loved every second of it. Don’t let your fear of having an active kiddo  be the...
11/02/2025

This little dude gave me a workout and I loved every second of it. Don’t let your fear of having an active kiddo be the reason you don’t schedule your session. I promise we will get some beautiful images! You’d never know just how many steps he had us running between shots! Bring snacks, comfy shoes, and a good attitude and we will get it done!!

Fall at Maine Audubon is my favorite time of year. 🍂🍁 bonus: having some of the sweetest clients ever!
10/29/2025

Fall at Maine Audubon is my favorite time of year. 🍂🍁 bonus: having some of the sweetest clients ever!

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Main Street
Cumberland Foreside, ME
04021

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