An engagement session is an hour or two of photographs taken months before the wedding, usually somewhere that means something to you. Couples book it for save-the-dates and a sign-in book, but the real reason we recommend one alongside our wedding photography packages is that it is a rehearsal. By the wedding you know how we work, we know how you move together, and the first twenty minutes of nervous posing have already happened. Here is how to get the most from it.
When to schedule it
Six to nine months before the wedding is the sweet spot: early enough to use the photos for save-the-dates (which go out six to eight months ahead) and to still change your mind about the wedding-day portrait plan. If you want a particular season in the pictures, book for it: fall colour in southern Wisconsin peaks in the second and third weeks of October, apple blossom and lilac in mid-May, and lake sessions are warmest from late June to mid-September. The time of day matters more than the season. We shoot in the last ninety minutes before sunset or, less often, the first hour after sunrise, when the light is low, warm and soft. Midday sun on a clear day is the one thing to avoid.
Choosing a location
The best locations are ones with a reason. Where you met, a trail you hike, your neighbourhood, the lake you spend summers at. Failing that, choose for variety: somewhere with two or three distinct backgrounds within a short walk, so an hour produces more than one look. Across our service area a few places work for almost everyone:
- Madison: the UW Arboretum, Olbrich Botanical Gardens (outdoor photography permit required), Picnic Point and the Lakeshore Path, the Capitol Square and State Street, Olin Park for the skyline across Lake Monona. Our Madison page lists more.
- Milwaukee: the Third Ward and Riverwalk, Lake Park and the North Point Lighthouse, Veterans Park on the lakefront, the Milwaukee Art Museum grounds at sunset. Milwaukee County Parks require a permit for posed sessions.
- Chicago: Lincoln Park and the Nature Boardwalk with the skyline behind, the Riverwalk, Promontory Point, Olive Park by Navy Pier. The Chicago Park District requires permits for some locations.
- Destination: Lake Geneva’s shore path, Devil’s Lake bluffs (state park vehicle sticker needed), the Door County shoreline, the Driftless hills around Dodgeville and Mineral Point.
Two locations in one session is fine if they are within fifteen minutes of each other; three is usually one too many. Check whether a location needs a permit for professional photography; most botanical gardens and many county parks do, and we will tell you if yours does.
What to wear
- Bring two outfits: one relaxed and one dressed up. Change in the car between locations.
- Coordinate, do not match. Pick a palette of two or three colours that suit the location (earth tones for fall woods, soft neutrals or blues for the lake) and avoid identical outfits.
- Solid colours and simple textures photograph better than small patterns, large logos and neon. Long dresses and skirts move beautifully in wind.
- Dress for the actual temperature. Cold, miserable people look cold and miserable; a coat you love is a fine engagement-session outfit in November.
- Shoes you can walk in. We will be moving; bring the heels in a bag if you want them for a few frames.
- If you want a ring close-up, have the nails done a day or two before.
What happens during the session
We start with the easy things: walking, talking, holding hands, not looking at the camera. Most of the best frames of any session come from movement rather than poses. Then a few stiller portraits, individually and together, then the ring, then whatever you brought: the dog, a blanket, a bottle of something. Ninety minutes gives us two locations or one location with a sunset. If you have a video package with us we can also film short pieces during the session for a save-the-date clip or to open your wedding film.
Props, pets and people
Dogs are welcome and are usually the best thing in the photos; bring someone to hold the lead for the frames without them. Props work when they are already part of your life (bikes, a canoe, instruments) and look like props when they are bought for the day. Champagne is fine; glitter and confetti are banned at most parks and we would rather not be the reason.
How the session improves the wedding day
Three things carry over. You stop noticing the camera, which is the single biggest difference between stiff wedding portraits and natural ones. We learn which side you prefer, how tall you are together, who laughs first; small things that save minutes on a wedding day when minutes are scarce. And we test the plan: if the portrait spot you had in mind turns out to be a parking lot at 5 pm, better to find out in May.
Frequently asked questions
How long is an engagement session?
Ours run 60 to 90 minutes, which is enough for two outfits and either two nearby locations or one location through sunset.
When should we do our engagement photos?
Six to nine months before the wedding, in the season you want in the pictures, timed for the last ninety minutes before sunset.
How many photos do we get?
Typically 50 to 100 edited, high-resolution images delivered in an online gallery within two to four weeks, with a print release.
Can we add an engagement session to a wedding package?
Yes. An engagement session can be added to any VIDART wedding photography or videography package; ask for the current rate when you check your date.
Can we bring our dog?
Yes. Bring a second person to hold the lead between shots, treats, and a towel if there is water nearby.
VIDART photographs and films weddings across Wisconsin, Illinois, Iowa, Minnesota, Indiana, Missouri and Michigan: $1,500 for a half day, $3,000 for a full day, photo and video together from $3,000, no travel fee.
Related reading
- How to Pose for Wedding Photos: A Photographer’s Guide to Looking Natural
- Wedding Photo Ideas and Shot List: What to Capture From Getting Ready to the Last Dance
- The Best Time of Year to Get Married in Wisconsin: Weather, Light and Prices by Month
- How Much Does a Wedding Photographer Cost in Wisconsin? (2026 Guide)
An engagement session can be added to any wedding photography package; see the Madison wedding photographer page for local portrait spots.
