2025 Fall Portrait Sessions – Twig & Olive Photography

How to Book Your Fall Wisconsin Portrait Session

Are you looking to book your fall portrait session? As the vibrant colors of autumn unfold, there’s no better time to photograph your loved ones in all its warmth and beauty. Whether you’re a couple seeking to preserve your love story, a family cherishing togetherness, a high school senior celebrating graduation, or someone who wants to capture the season’s beauty, our fall portrait sessions offer an unmatched product and experience.

Our fall sessions are primarily around the beautiful Madison, Wisconsin area in Dane County, where the autumn foliage creates a picturesque setting for your portraits. However, our passion for photography takes us beyond local borders, and we’re excited to come to your area. These areas include Chicago, Dubuque, Minneapolis, Lake Elmo, Rochester, Milwaukee, Central Florida, and San Diego. Check out our calendar to see where we’re headed next!

A young boy lies on his mother's lap, gazing up with a calm expression, surrounded by intricate patterns and soft fabrics.
A family of four sits closely together, laughing and smiling amidst autumn foliage, as the sun sets behind them.
A mother in a flowing burgundy dress joyfully holds her young daughter in a sunlit field with autumn colors, surrounded by tall grasses and trees in the background.
A family of four running joyfully through a grassy field, with two young boys leading the way holding a football, followed by their parents.
A family of four, including a pregnant mother, stands in a sunlit field with autumn foliage, sharing a moment of joy and togetherness.
A family of six walks together in front of a rustic wooden barn, the mother in a flowing dress, and the children in coordinated outfits.
A young boy peeks through tall white flowers in a sunlit field, with a gentle smile on his face, wearing a denim jacket.
Three young girls with blonde hair sharing a joyful moment, with the girl in the center smiling brightly while wearing black-rimmed glasses, and the girl on the right wearing a wide-brimmed black hat.
A woman with dark hair whispers into a man's ear as he smiles, wearing glasses and a beige jacket in a natural outdoor setting.

Here are the quick details:

  • Capture Your Unique Story: Our Fall Portrait Sessions are perfect for everyone—from families to couples and individuals to entire generations. Certainly, all people and types of families are welcomed.

  • Customized Sessions: Whether you’re looking for a quick yet complete experience or a highly customized adventure, we offer a range of sessions to suit your fall portrait session.

  • Ideal & Beautiful Locations: Our sessions take place in breathtaking outdoor locations, highlighting the vibrant autumn foliage. We carefully select sites that provide a picturesque setting for your portraits, allowing the natural beauty of fall to enhance every shot. Some of our favorite locations include McCarthy Park, the UW Arboretum, and Token Creek Park.

  • Perfect Timing: Our sessions are available throughout the entire fall season. For those looking to capture that magical golden hour light, we offer special sunset priority sessions. This is the perfect opportunity to embrace the serene beauty of nature and let it shine in your portraits.

How to Book: Three Easy Steps

Pick Your Session

First, choose from the five session types below

Purchase Your Session

Next, add the session to your cart and pay

Schedule Your Session

Finally, email us to schedule your date

Core Sessions | Mini and Deluxe

Our Core Sessions are designed for those who want a seamless and beautiful experience capturing the joy and connection of their family or loved ones. Our Mini Session offers a quick yet meaningful experience, allowing you to savor the moment without a major time commitment. For those seeking a more immersive experience, our Deluxe Session provides the perfect opportunity to dive deeper into the story of your family, allowing for more time to explore unique settings and capture a variety of authentic moments. Both sessions are crafted to provide a personalized and enjoyable experience, resulting in stunning images that you’ll treasure for years to come.

Mini Session

A young boy with curly brown hair and bright blue eyes makes a playful face while standing on a leaf-covered path wearing a brown jacket and plaid shirt.

  • Duration: 30 minutes

  • Gallery: 30-45 images
  • Included: 10 digital images (additional images can be purchased)
  • Cost: $300

  • Ideal For: Those seeking a quick session to experience the essence of fall. Perfect for updating family photos or capturing a special milestones.

Deluxe Session

Two young girls in floral dresses playfully surrounded by dandelion seeds in a sunlit field, expressing joy and wonder.
  • Duration: 60 minutes
  • Gallery: 50-75 images
  • Included: All digital images + 11×14 mounted lustre print
  • Cost: $700
  • Ideal For: Families or couples looking for a more in-depth photography experience. With more time and a larger gallery, you’ll have plenty of options to choose smiles and candid moments.

Heirloom Sessions | Adventure, Generations, and Storytelling

Our Heirloom Sessions are designed for those who want to celebrate their unique story through an immersive and personalized photography experience. Whether you’re an adventurous family eager to explore beautiful landscapes, a large family wishing to honor generational bonds, or individuals looking to highlight meaningful connections, our Heirloom Sessions offer something truly special. Each session is thoughtfully crafted to reflect the individuality and spirit of your relationships, set against the stunning backdrop of the fall season. With the magical golden hour lighting, these sessions provide a perfect blend of creativity and authenticity, ensuring that every moment is beautifully captured and cherished for generations. Every Heirloom session includes the following:

  • Duration: 90 minutes
  • Gallery: 75-100 images
  • Included: All digital images + 4×6 signature heirloom print box
  • Sunset Priority: Golden hour sessions for those magical and warm images that capture the essence of togetherness.
  • Cost: $975

Adventure Session

Three young boys building a stone tower outdoors, with their mother watching in the background, surrounded by autumn foliage.
  • Ideal For: Adventurous families or couples looking to explore and create unique images that reflect their dynamic and fun-loving spirit.

Generations Session

A group of people sitting and standing against a large greenhouse window, each with distinct poses, surrounded by autumn foliage.
  • Ideal For: Large family gatherings or multi-generational portraits that celebrate the bonds between generations.

Storytelling Session

A young couple sitting close together in a field of tall autumn grasses, with the man gently kissing the woman's cheek as they hold hands.
  • Ideal For: Couples, best friends, or anyone wishing to capture the intimate, meaningful, and authentic connections in their life.

Not ready to book a fall portrait session? Let’s get you what you need!

Testimonials:

I just wanted to say thank you.

Thank you for capturing my babies and us just as we are in this wild and chaotic season. 2 under 2 is HARD, but these photos made me FEEL and I haven’t done that in a long time 😭❤️thank you for reminding me of my “why” and for giving me precious memories to hang on my walls for years to come!

Hope to see you again when you’re back in Florida!

Kristen W

Wow!!!! The photos are AMAZING! Doug you really captured the personalities of the kids and they look so beautiful! You weren’t joking about Harrison- he really slayed it and even some smiles from Colette. Thank you for capturing this moment in time for us. We love them!! I love the random cows…so very Wisconsin!!

Erica K
Just wanted to send a real quick THANK YOU.

I didn’t know what to expect with our session, we have only used a friend photographer in the past where we used to live up by Eagle River.
My kids were not looking forward to last night but Doug, you killed it. They loved it. The whole experience was so refreshing and my kids are already asking to do it again next year :)
We are looking forward to more sessions in the future.
Thanks so so much!

Megan W
Just wanted to share that we had such a fun experience on Monday! Braeden is REALLY coming into his own, he’s not as shy and so, so silly and interactive these days!!

He could not stop talking about Mr Doug after we left – he wanted to know where you were, what you were doing, where you lived, if you had kids – I said yes, they have 4! Then he wanted to know where your kids were, how old, etc. We talked about how Miss Courtney has done a lot of our shoots in the past too! So he started asking where you were Courtney – I told him I wasn’t totally sure, but that you might be with the kids. Then he asked when he can come play with them. He promised not to toot on anyone – highlight of the session, talking about toots. BOYS. :) Thanks for always being the best photographers! Can’t wait to see the pics when they’re ready!

Bridget B
I had to tell you – right after we pulled out of the parking lot, Wren said “I like that guy, can he take our pictures next year, too?”

It takes her a while to warm up to people, but you’re in now! Juniper obviously loved you, too!

Amanda B
Oh. My. GOSH!!!

These are absolutely amazing. Thank you so much for Doug’s amazing photography (and patience w kids) and this amazing editing work!

Amber S

Thank you so much for a great session on Friday! From the rescheduling to the wardrobe help and then being a toddler whisperer, it all was much appreciated! The pics you got of Nora and Baker just make my heart happy, so thank you!!

Lisa P
Hey, I just wanted to pass on a huge thank you to Doug. Not only did you help my boys forget that they were cold/annoyed with their clothes/uncomfortable/rather be playing Xbox/blah blah blah, you had them cracking up and made the whole session fun and painless. Not to mention, cracking a genuine smile from the teen. ☺️ I know your brand is built on authentic smiles and all, but you’re truly a master at your craft. Thanks again!
Angela A
We just wanted to thank Doug for the amazing photos. We honestly didn’t think we got any happy ones of our little guy as he was so tired 🙂 they all turned out so beautiful. Just want to say thank you and that you all are so talented at what you do!
Brianna S