Jessica Ann Photography

Jessica Ann Photography

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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.

Photos from Jessica Ann Photography's post 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!

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. πŸ˜†
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! πŸ’’πŸ’

Photos from Jessica Ann Photography's post 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!

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". πŸ€ͺ

Photos from Jessica Ann Photography's post 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. πŸ˜†
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! πŸ™‹β€β™€οΈ

Photos from Jessica Ann Photography's post 09/07/2026

I'm always a little nervous when I get to a wedding where I don't personally know anyone, but the second I pulled in to Katie and Heath's wedding, I was welcomed by everyone and spent the day feeling like I was a part of their family. Katie, Heath and their family and friends were the best example of how to enjoy every moment of the day, filling the day with so much laughter and love.
Their wedding was held on a farm in Vermont, with Heath and Katie being only the second couple to ever be married there, the first being the owners of the beautiful property. Heath has worked the farm since he was young, so it was a very special location for him and his family.
Congratulations Katie and Heath, thank you for letting me be a part of your special day, and thanks for keeping me laughing the entire day!

~Makeup Sabrina Henault
~Hair Emily B Hair Artistry LLC
~DJ Spotlight Entertainment
~Favors, maple syrup made by the bride and groom 🀩

08/31/2026

What I see when I open the camera on my phone and it's accidentally facing me πŸ˜†πŸ¦™

Photos from Jessica Ann Photography's post 08/31/2026

What a turn out at Pickle Fest yesterday! The vendors, the food, the weather, all amazing! Charlene performed such a cool fire show, after coming all the way from Virginia in honor of her grandmother, Theresa Dix, whose donation helped put on the event.
Many more photos to come!

08/18/2026

Marry the man who will carry your dress across wet grass without being asked. πŸ™ŒπŸ«Ά

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