Field Notes · An Honest Take
Should you have family photos taken every year?
A South Shore photographer's honest, unhurried answer — for the families who keep asking, and the ones who feel guilty for not booking.
The thesis
“The family who books every September always has the best long-running archive. The years you skip are almost never the years nothing happened.”
— What I would tell a friend, if a friend asked
South Shore Photography, based in Rockland, MA, photographs families on-location across Hingham, Scituate, Norwell, Duxbury, Marshfield, Cohasset, Hanover, Weymouth, and Plymouth. Photographer Chris McCarthy has guided dozens of South Shore families through the “do we book again this year?” question — here is his honest, no-pressure answer.
The question I get asked most often
Every spring and again every August, I get the same email. Some version of: “We did photos with you last fall and they came out beautiful — do we really need to book again this year? Are we one of those families who has to do this every year now?” It is a fair question, and after photographing hundreds of South Shore families across multiple sessions and multiple years, I have an honest answer. Annual family photos make a lot of sense for some families and almost none for others. Below is who falls into each camp, what the real trade-offs look like, and how the families with the best long-running archives actually pull it off.
I have a family I have photographed every September since 2019. Two girls, beach session, same general spot in Duxbury. In the fall of 2023 they skipped — kids' soccer schedule, a kitchen renovation, the usual perfectly reasonable reasons. They booked again in October 2024 and we caught up like nothing had happened. About six weeks after that session, their grandfather — who lived with them, who was in nearly every annual photo from 2019 through 2022 — passed away unexpectedly. The most recent photo of him with the kids was from 2022.
I am not telling that story to scare anyone into booking. I am telling it because it is the single clearest reason I have ever encountered for why an annual cadence is worth taking seriously. The years you skip are almost never the years nothing changes. The years you skip are the years you wish, in hindsight, you had not. That is the photographer-side argument in its bluntest form. The rest of this piece is the honest, balanced version.
Worth saying up front: I do not push annual sessions on anyone. I am a working South Shore family photographer, and my calendar is full whether any individual family books once a year or once every three years. The recommendation that follows is honestly what I would tell a friend.
Who annual makes sense for — and who can comfortably skip
Book yearly
Four kinds of families benefit clearly from a yearly rhythm.
Families with kids under ten.
Children change so quickly between ages two and ten that a two-year gap is essentially a different child. The toddler who needed to be carried in 2024 is a kindergartner with a missing front tooth in 2026 — and neither version exists in your archive if you only booked once. Annual is the cadence I recommend without hesitation.
Families with out-of-state grandparents.
Grandparents who do not live nearby lean on the annual photo more than anyone. It is what shows up on their refrigerator, what they hand to friends, what they look at when they miss the kids. Several of my repeat client families book their session specifically as a gift to grandparents.
Families navigating a transition.
A move, a divorce, a blended family forming, a deployment, a kid leaving for college — these are exactly the years to photograph. The instinct can be to wait until things settle down, but the in-between state is real and worth documenting.
Tradition-driven families.
Some families just love a yearly anchor — the September beach session has become as much a part of their fall as apple picking or homecoming. The annual session becomes a marker the kids look back on years later and remember as “something we always did.”
Space it out
Three kinds of families for whom annual is overkill — no guilt required.
Older kids, stable configuration.
If your kids are twelve and fifteen, no one is moving, no one is graduating in the next two years, and the family looks broadly the same year over year — every-other-year is plenty. You will not miss meaningful change in the gap.
Gallery wall already saturated.
If the photos from last year are not yet printed, framed, or on the wall, there is genuinely no need to book this year. Get value out of the existing archive first. Some of my repeat families do annual sessions but only print a wall piece every two or three years, which is also fine.
Chronic scheduling difficulty.
If booking even one session every fall feels like climbing a mountain, three sessions in two years will be miserable. Be honest with yourself. A great session every two or three years that you actually enjoy is worth more than a forced annual session you resent.
The photographer-side argument for annual
I have to be honest about what I see from behind the camera. The families I have photographed every September for five or six years have, without exception, the strongest long-running archives I have ever produced. Year by year, the kids grow, the parents age subtly, the family changes shape — and the visual record of all of it is continuous. There is no “wait, when was that?” gap. There is no missing year. There is a story.
The flip side of that is the pattern I mentioned in the opening anecdote: the gap year is, with strange frequency, the year a grandparent passed, a parent got sick, someone graduated unexpectedly, a marriage ended, a baby arrived. I do not think this is mystical — I think it is just statistically true that in any given year, something significant happens in most families, and the year you skip is the year that thing went unphotographed.
Read more about why this matters specifically for moms — statistically the most under-photographed family members across all cadences — in my post on why mom should be in the family photos.
The honest case against annual
There are real downsides to annual sessions and any photographer who pretends otherwise is selling you something:
- Cost compounds.
- A $450 session once a year is $5,400 across the twelve years your kids are kids. That is a real number. It is roughly $37.50 a month if you average it out, which is the framing that makes it feel manageable, but the gross number is not nothing.
- Scheduling fatigue is real.
- Booking, prepping outfits, getting everyone in the car, smiling on cue — doing that every fall for ten years takes effort. Some families love it. Some families burn out around year four.
- Kids can hit a wall.
- Younger kids generally love the attention. Tweens and early teens sometimes resent the annual session, especially if it always happens the same way in the same place. That resentment shows in the photographs.
- Creative fatigue, both sides.
- If every September is a Duxbury beach session with the same wardrobe palette, by year five everyone — including me — is going to feel the repetition. Annual sessions only stay interesting if they evolve.
What annual family photos actually cost — spread the way most families experience the spend.
- One session, on-location, South Shore
- $450
- × twelve years your kids are kids
- $5,400
- Spread across the year — per month
- $37.50
- Same monthly bracket as
- a streaming bundle · one dinner out
Framed that way it sits in the same budget category as ordinary household subscriptions — which is what makes it tractable for most families who otherwise feel sticker shock at the per-session number.
Talk Through Your Cadence
Not sure whether annual makes sense for your family?
I am happy to talk through what your archive looks like, what is changing this year, and what cadence would actually work — no pressure to book.
Session-fatigue solutions that actually work
If you want the annual archive but worry about burning out, the families who pull it off long-term tend to use one or more of these strategies:
- i.
Alternate full sessions and lifestyle at-home.
Year one is a beach golden-hour session, year two is a relaxed at-home morning with coffee, pancakes, and the kids in pajamas. The variety keeps it feeling fresh and produces a more rounded archive than five identical beach sessions in a row.
- ii.
Rotate locations on a three-year cycle.
Beach in year one, inland park or conservation land in year two, downtown or harbor in year three. Then loop. Each location feels new by the time you return to it. My park guide and the locations-beyond-beach piece are good starting points for breaking out of a beach-only rotation.
- iii.
Joint sessions with cousins or grandparents.
Extended-family sessions split the cost across multiple households and produce images you cannot get any other way. My guide on extended-family sessions for groups of fifteen-plus covers the logistics of pulling these off well.
- iv.
Mini sessions in shoulder years.
If a full annual session feels like too much, a twenty- or thirty-minute mini in spring or fall keeps the archive moving without the same cost or scheduling load. My fall mini-session post walks through how those work.
- v.
Theme the session.
One year is “kids and grandparents only.” The next is “just the four of us.” The next is “everyone in the kitchen baking.” Theming gives the year a reason to exist beyond “it has been a year.”
How to make each annual session genuinely different
The single biggest reason annual sessions get stale is that families default to the same location, same season, same wardrobe palette every year. Five small levers fix that:
Rotate locations on purpose.Beach this year, inland park or carriage road next year, at-home lifestyle the year after, downtown or harbor in year four. The archive starts to feel like a tour of the South Shore rather than five copies of the same photograph.
Anchor on a milestone.Tie the year's session to something specific — first day of kindergarten, middle-school start, a graduation, a sibling's arrival. Future-you, looking at the archive, will remember that year as “the kindergarten one” rather than “another fall beach session.”
Rotate seasons.Most South Shore families default to fall. Try spring once. Try late summer. A January session in soft winter light at the harbor is a wildly different image than another October beach. My holiday planning post covers winter timing in detail.
Build around an activity.Sledding. Baking. Tide-pooling. A picnic. Apple picking. Activity-based sessions produce genuine expressions and movement that posed beach lineups never will.
Change wardrobe palettes year over year.If last year was cream and camel, try forest green and burgundy. If last year was navy and white, try rust and oatmeal. The palette change alone makes images feel distinct in the archive.
The compounding archive argument
A starter image
One photo. The kids at this exact age, this exact size. Useful, lovely, alone.
The beginning of an arc
Side by side, you can already see the story. Front teeth come and go.
A genuine archive
A wall of framed prints. A yearbook. The grandparents have it framed in order.
A family history
A continuous visual record of an entire childhood — nothing missing.
One frame per fall — the archive compounds
At every-other-year or every-three-year cadence, you have snapshots. Good snapshots, often great ones — but snapshots. At annual cadence, you have a story. That is the distinction. Whether your family wants the story or is happy with the snapshots is genuinely a personal call, and there is no wrong answer.
The families I have photographed longest often print their archive as a wall-mounted gallery sequence — a row of framed prints, one per year, that grows by one frame every fall. It is one of my favorite things to see when I visit a repeat client. The wall itself becomes part of the family. For more on what happens after the session — print products, gallery delivery, how to actually use these images — see my family photo delivery timeline post.
Best time of year to schedule
For families committing to annual sessions, the single most useful thing you can do is pick a month and own it. September is the most popular anchor on my calendar — light is excellent, school is back but not yet hectic, the marsh grass and early foliage start to turn, and it is the natural lead-in to holiday card season. October is the close second, with peak South Shore foliage but tighter availability and weather risk.
Whatever month you pick, the families with the smoothest annual rhythms book sixty to ninety days in advance every year. They reach out in July for a September session, in August for October. By the time the calendar tips into peak fall, my weekend golden-hour slots are gone — sometimes within days of opening. Booking early is not me applying pressure, it is the actual mechanics of how the calendar fills.
If September and October fill up, do not default to skipping the year. May, early June, and early September shoulder-season slots are routinely available and produce beautiful work. My session-day checklist works for any month — the planning structure is the same regardless of season.
Frequently asked questions
How much does annual family photos cost over time?
A South Shore family portrait session typically runs around $450. Booked annually for twelve years, that comes out to roughly $5,400 over the life of your kids being kids — about $37.50 per month when you spread it across the year. Framed that way it sits in the same budget category as a single dinner out or a streaming bundle, which makes it tractable for most families who otherwise feel sticker shock at the per-session number.
What about every-other-year family photos?
Every other year is a great compromise once your kids are about seven or older and physical change slows down. I pair it with a short mini session in the off year — twenty or thirty minutes, lower investment — so you still get one fresh image to print and send each holiday. That cadence captures the same arc as annual sessions without the same scheduling load or cost.
Do you offer a multi-year family portrait package?
Yes. Families can prebook three sessions over two years and lock in current-year pricing for all three. A deposit secures the package, and we schedule each session as it approaches rather than committing to specific dates two years out. It is the simplest way I have found to give families the archive value of annual sessions without the friction of rebooking from scratch every fall.
What if we miss a year of family photos?
No judgment and no penalty. Life happens. The families who skip a year and then book a January or April session usually fall right back into their annual rhythm the following fall. The archive does not have to be perfectly even — it just has to keep growing. A makeup session a few months late counts.
Lock In Your Annual Date
First session or sixth — let's hold a date.
Whether you are starting your archive or adding to it, I would be glad to walk you through what this year's session could look like across the South Shore.
The Pillar Guide
The Complete Guide to Family Portraits on the South Shore
This post focuses on how often to book family photos. For the full overview — every South Shore family portrait location, wardrobe by season, what to bring, and how to plan your session — read the complete pillar guide.
Read the South Shore family portrait pillar guide →
ABOUT THE AUTHOR
Chris McCarthy is a portrait photographer based in Rockland, MA who has been photographing the South Shore full-time since opening his studio in 2014 — more than a decade of outdoor and lifestyle portrait work across the region. He specializes in headshots, senior portraits, branding, family, and maternity photography — shooting at his studio at 83 E Water Street and on-location throughout southeastern Massachusetts at places like World's End, Scituate Harbor, Duxbury Beach, and the North River conservation land in Norwell.
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