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Serving Boston and surrounding areas including Dedham, Needham, Wellesley, Newton, Brookline, Westwood, Medfield, Norwood, Canton, Millis, Wayland, Watertown, Milton, Walpole, Sharon, Lexington, Dover and more!

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Outdoor Family Sessions

Luxury Service, Effortless Experience.
Capture this moment without the stress of doing it all yourself.

Your Outdoor Family Session

Luxury Outdoor Family Photography in the Boston and Greater Boston Area

You’ll never regret having beautiful photos with your kids, but you might regret putting them off!

 

Whether this is your first time booking family portraits or you’re ready for a more elevated experience, now is the perfect time to do it.

The truth is, life won’t slow down; and there’s no perfect moment to get in the frame. But that’s exactly why now is the right time.

At Chickey Little Photography, I specialize in outdoor family sessions that feel relaxed, meaningful, and totally personal. For Boston-area families who want beautiful images without the stress, I take care of everything—from in-home hair and makeup to wardrobe styling, location planning, and even hanging your final wall art. Want to keep it simple? I’ll come to your own backyard and turn it into something magical.

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 You only get one chance to capture your family as they are right now.
Don’t miss it or settle for photos that feel stiff, rushed or forgettable.


I specialize in full-service, family photography sessions that are tailored to you.

Whether you're envisioning a playful session in your own backyard, a golden hour shoot at a favorite local spot, an early morning session at the beach or something calm and cozy at home, every session is thoughtfully planned to reflect your family's unique connections - naturally and beautifully with just the right amount of guidance.

How it works

We Connect

We Plan

We Shoot

We Create

I know the phone can be scary, but don't worry - it's just a friendly chat! This way I can learn about you and your family, your goals, your style, and what matters most to you.

I’ll come to your home and we'll look at your space, customize the shots, and plan your family's wardrobe. You don’t have to figure out anything yourself!

Your session will be a mix of gently guided moments and natural, candid magic, so you get variety without stress.

Within two weeks, we'll meet back and I’ll walk you through your images and help design artwork that fits your home (and your life). I even handle installation!

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Chelsea thought about everything from location, styling/ outfit suggestions to what kind of images we want to see on our wall/ family album. She uses all those ideas to make the family session fun and efficient.
She is able to capture moments of fun, as well as getting my two energetic kids to look at the camera, quickly find those smiles when needed.
We have worked with her three times and every time we enjoy the process, and most of all, love all the pieces she helped put together from smaller gifts to wall art. Her professionalism is also remarkable, she would answer questions right away and we never had to wait.

What's included?

  • Style & Concept Consultation
    We’ll meet at your home before your session to plan wardrobe, color palette, shots, artwork goals, and overall vision.
    [Learn more about the process →]

  • In Person Wardrobe guidance
    You’ll receive personalized styling support, including access to a curated collection of dresses for moms and outfit options for babies and toddlers that photograph beautifully and feel true to your style. We’ll also do an in-person consultation using your own closet to help pull everything together with ease.

  • In-home hair & makeup for mom
    My professional artist comes right to your home on session day, so you can relax and feel your best without having to lift a finger. A quick pre-session survey helps tailor the look to your
      preferences.

  • Digital & hard copy prep guides
    You’ll receive beautifully designed guides to walk you through what to expect, how to prepare your space, and how to make the most of your session

  • Customized shot list + relaxed session flow
    Your session is tailored to your family, blending guided portraits, sibling moments, and unscripted storytelling; all planned around your comfort and preferences.

  • Ordering appointment (2–3 weeks post-session)
    We’ll view your images together, and I’ll guide you through the process of choosing your favorites—it’s relaxed, interactive, and actually one of the best parts! I’ll show you custom wall art mockups so you can visualize exactly how your images could look in your home. While artwork design and installation is always available, you’re never expected to order anything beyond what feels right for your family.

We're the right fit if...

  • You want a full-service photography experience—from start to finish

  • You value quality over quantity and are looking for custom artwork, not just digitals

  • You want to feel taken care of with in-home hair and makeup and wardrobe support

  • You’re tired of doing it all yourself (planning outfits, picking a location, crossing fingers for cooperation)

  • You want to actually be in the photos this time—not just take them

  • You care more about connection and real moments than perfect posing

  • You want photos that reflect your family as they are right now—beautifully and authentically

  • You’re looking for someone who understands how to work with kids and keeps things relaxed

  • You’re ready to turn these fleeting moments into heirloom artwork for your home

  • Sound like you? Let’s create something meaningful—without the stress.

What you'll walk away with:

  • A calm, guided experience that leaves you feeling confident, not stressed

  • Photos that feel like you - honest, emotional, and beautifully crafted

  • Artwork and heirlooms that you'll be proud to display

  • Memories preserved in a way your family will treasure and talk about for years to come

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FAQ's

What should we wear for our session?
Don’t stress, I’ve got you covered. We’ll go over everything during your in-home style and concept consultation, where I’ll help you choose outfits that coordinate beautifully with the location, season, and your family’s style. And if you like I can even make you a personalized style board.

Can we include grandparents or extended family?
Absolutely. Just let me know ahead of time if additional family members will be joining so I can plan for enough time and adjust the flow of the session to include everyone.

What happens if it rains?
New England weather keeps us on our toes! I keep a close eye on the forecast leading up to your session, and if it looks like we’ll get rained out, we’ll reschedule to the next mutually available date -no stress.

What time of day do sessions take place?
Outdoor sessions are scheduled around the best natural light, usually early morning or about 90 minutes before sunset. Don’t worry, I’ll help you pick the best time based on your kids’ routines and the time of year.

How long does the session last?
Most outdoor sessions last about one hour. That gives us plenty of time for a mix of candid, playful moments and softly guided portraits without anyone feeling rushed. Sometimes younger children don't make it that long, and sometimes we're having so much fun we run over. I don't bring a stopwatch ;) And if you're looking for something more extensive I'm always willing to accommodate. We will go over custom options during our Discovery Call.

What if my kids don’t cooperate?
Totally normal! My approach is relaxed and child-led. We’ll play games, explore the space, and follow their lead. The goal isn’t stiff smiles, it’s capturing genuine connection and joy.

Where will the session take place?
I have several beautiful, tried-and-true locations I can recommend, or I’m happy to come to your favorite outdoor spot - even your own backyard can be the perfect setting. We’ll talk it through during your consultation. I'm also always happy to discuss the option of an at-home storytelling documentary session - they're amazing!

When will we see the photos?
About two weeks after your session, we’ll meet for your in-home ordering appointment, where you’ll view a curated gallery and choose the heirloom artwork that fits your family and home.

Can we bring our dog?
Yes! Pets are family too. Just let me know so we can choose a pet-friendly location and make a plan for wrangling them when they’re not in the shot.

What do your outdoor sessions include?
Every session includes the full-service experience - your style consultation, location planning, the session itself, an in-home ordering appointment, and access to heirloom products like albums, prints, and custom wall art.

What if I want to do something at my home?

That’s actually one of my favorite things to do. My in-home documentary sessions are perfect for capturing your family in a way that feels real, comfortable, and meaningful. We can focus on the everyday moments that matter most—baking in the kitchen, reading on the couch, playing in the yard—or we can blend that with some lightly posed family portraits outside in your own space. It’s relaxed, personal, and tailored entirely to you.

What should I expect to invest?

Every family's story is different, and my sessions are all about creating something personal and lasting. This is a full-service experience for families who want a hands-on, customized process from capturing meaningful moments to designing artwork that truly fits your home and lifestyle.

When you book, your session fee includes a credit toward your image purchase. After your session, we’ll meet for a relaxed ordering appointment where you’ll choose the images you love most. Each selection includes both the digital file and a printed version (either in a custom album or matted print collection).

Final spending all depends on your goals and what you choose. I’ll walk you through everything so you can make decisions with clarity and confidence and you only buy what you love!

Portfolio

 

601 Washington St, Norwood MA
Serving the Boston and surrounding area including, Brookline, Newton, Needham, Norwood, Westwood, Wellesley, Walpole, Dedham, Canton, and Milton and beyond. Happy to travel, just ask!

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