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

08/18/2026

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

Photos from Jessica Ann Photography's post 08/15/2026

Anyone with littles knows it's not exactly easy to get them to want to look at a camera for an hour. I like to use the silly word method, and today's post is brought to you by "chicken bear", which big bro made up on the spot and was the perfect amount of silly for his little sis. Thinking about hiring him as my assistant for all future family shoots. πŸ˜†πŸ”πŸ»

08/10/2026

The saying goes, "a wet knot is harder to untie", and Bella and Jeremy tied the knot just in time as the thunder rolled in. After the storm ended we were able to scoot down for a few beautiful formals on the course, which goes to show that rain on your wedding day is good luck! πŸ₯°
Congratulations Bella and Jeremy!!

Photos from Jessica Ann Photography's post 08/06/2026

It was almost impossible for me to choose my favorites for this post, these four are just too cute! 😍

Photos from Jessica Ann Photography's post 08/05/2026

Shout out to the amazing hair and makeup team at our styled shoot! Our models both had such natural beauty, and these girls did an incredible job enhancing that beauty and turning it into perfection!
From Four One Three Salon: hairstylists Shelby and Lexi, and makeup artist Skylar.

𝐒𝐀𝐲π₯𝐚𝐫 π‘πžπ§ππžπ«

Photos from Jessica Ann Photography's post 07/27/2026

I'll probably spend the next two years posting about our amazing styled shoot (thanks to Rachel Reynolds Events), and Blonde N Boozy definitely deserves her own post.
Kayla is the perfect mix of professional and fun, her drinks are amazing, and how cool is this trailer?! Not to mention she's a bad ass who hauls and sets up her trailer all by herself. πŸ’ͺ
If you need a mobile bar for your wedding or event, Kayla is your girl! 🍸🍾

Photos from Jessica Ann Photography's post 07/25/2026

If you hire me for an event, at some point I'll end up with the toddlers making a mess of your new driveway. Their cuteness will make up for how not sorry I am. πŸ˜„

Photos from Jessica Ann Photography's post 07/20/2026

Jumping into Monday like:

Photos from Jessica Ann Photography's post 07/17/2026

Jupiter, the Band played at an anniversary party I shot this month, and what a great band they are! They had me singing along all afternoon. Plus, how cool are their cymbals and guitar strings?! 🎸πŸ₯

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Adams, MA
01220