Jessica Ann Photography

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Jessica Ann Photography Berkshire County wedding, event and family photographer I hope you enjoy my work, and I hope to be capturing moments for years to come!

My love for photography started as a child, when my grandfather would take out his slides and projector and we would go through all of his pictures. As an adult, after being in a few weddings, and seeing what went on behind the scenes, I realized that I wanted to be the person to capture the moments of such a special day. in 2013, I bought my first entry level DSLR (ok, ok, my mom bought it for me for Christmas), and spent my free time learning photography. I love being a part of the best day of a couple's life, and capturing all the love and beauty that is shared throughout their special day.

The cutest little apple 🍎
10/14/2026

The cutest little apple 🍎

Can we talk about how perfect this tree is for a fall ceremony?! 🍂🍁Can we also talk about how awkward it is for me to be...
10/10/2026

Can we talk about how perfect this tree is for a fall ceremony?! 🍂🍁
Can we also talk about how awkward it is for me to be running around, crunching leaves during a wedding ceremony...I feel like the person in a movie theater opening a bag of candy 😆🤦‍♀️
I'm fully open for fall 2027 weddings, and looking forward to running through more leaves! 😁

Jada and Darren chose to do their own private wedding vows outside the chapel before their ceremony, and it was truly sp...
10/07/2026

Jada and Darren chose to do their own private wedding vows outside the chapel before their ceremony, and it was truly special. The love these two have for one another is heartwarming. 🥰

That's a wrap on my 2026 wedding season! What an absolutely gorgeous fall day for Natasha and Udit, Sarah Morgan was def...
10/05/2026

That's a wrap on my 2026 wedding season! What an absolutely gorgeous fall day for Natasha and Udit, Sarah Morgan was definitely giving them her blessing. Stay tuned for more photos of my own personal ghost hunt/aka this beautiful wedding day 😍

When you choose me for your wedding, you're getting more than just a photographer. I'll be there to help however I can, ...
10/02/2026

When you choose me for your wedding, you're getting more than just a photographer. I'll be there to help however I can, whether it's keeping everyone on time, snapping the mother of the groom's dress, helping to set up your dessert table, whatever it takes for your day to go as smoothly as possible. I want to help make sure that your wedding day is the happiest day of your life. (Just know that I'm absolutely going to take a cupcake for my ride home. 🤭)

Thanks Pixelated Photography for capturing a piece of what I do behind the scenes 😍

The luck of having rain on a wedding day wasn't just for the bride and groom this past weekend, but for all of us who we...
09/28/2026

The luck of having rain on a wedding day wasn't just for the bride and groom this past weekend, but for all of us who were lucky enough to witness the pure, unconditional love that radiated off these two. Congratulations Jada and Darren!

I couldn't leave today's wedding without getting a picture of how ridiculous I look next to the groom. In my defense, he...
09/27/2026

I couldn't leave today's wedding without getting a picture of how ridiculous I look next to the groom. In my defense, he's REALLY tall. 😆
I might start advertising myself as the only wedding photographer in Berkshire County that you can carry around in your pocket. 🤭
Booking now for 2027/2028 weddings! 💒💍

What a turn out for Pickle Fest! After the original date was rained out, the weather ended up being absolutely perfect f...
09/22/2026

What a turn out for Pickle Fest! After the original date was rained out, the weather ended up being absolutely perfect for the rain date! Annmarie and Mike (FEWD TRUCK I Scream FEWD TRUCK) went above and beyond putting on this event, and it certainly showed!
There were way too many amazing vendors to name them all, but I will say I had an incredibly refreshing lemonade from Two Sisters' Spirits Mobile Bar, LLC, delicious hot dogs from Good Dogs Hotdogs, and obviously the first thing I did was go see the animals at McKay’s Family Farm Market. I'm already excited for next year!!!

Full album: https://jessicaannphotographyma.pixieset.com/picklefest/
Vendors, please feel free to download and share!

Weddings go by so fast, I sometimes forget some of the shots I took. This one made me LOL when I opened it. Textbook def...
09/20/2026

Weddings go by so fast, I sometimes forget some of the shots I took. This one made me LOL when I opened it. Textbook definition of "Like father, like daughter". 🤪

I love the weddings where, the minute I walk in the door, I'm met with pure sass from one of the kids. This little mama ...
09/13/2026

I love the weddings where, the minute I walk in the door, I'm met with pure sass from one of the kids. This little mama did not disappoint. 😆
If you want someone who is going to accept whatever your child throws at me, (and most likely give it back to them 🤭) I'm your girl! 🙋‍♀️

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Adams, MA
01220

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