Twenty unhurried, golden-hour minutes at the prettiest spots in Westport, Trumbull & Monroe. Real moments, not stiff poses. Ten fully edited images in a private gallery within one week. Perfect for holiday cards, grandparents, and the mantel — book early, slots are capped at six families an evening.
Westport
Sunday, August 2 · 6:00–8:00 pm
Open meadows, stone walls, and big-sky light. Classic New England.
Parking: Free on-site lot (25 Rte-136), open to all — no permit needed.
State Park · Westport
Sat & Sun, Aug 29–30 · 6:00–7:45 pm
Meadow, tree lines & beach in one. Golden grass at golden hour.
Parking: Free for CT-registered vehicles (Passport to the Parks). Out-of-state plates pay a ~$22 state day-pass at the gate.
Trumbull · Residents only
Sat & Sun, Sept 12–13 · 5:30–7:15 pm
Rustic stream, stone & woodland. A quieter, storybook backdrop.
Trumbull residents only: a valid Trumbull park sticker is required to park (enforced year-round). This weekend is reserved for Trumbull families with a park sticker.
Great Hollow Lake · Monroe
Sat & Sun, Sept 19–20 · 5:15–7:00 pm
Sixteen-acre lake, woods & open fields. Water-view golden hour.
Parking: Open to all — the resident-sticker rule ends after Labor Day, so no pass needed for these dates. Free lakeside lot.
Westport
Sat & Sun, Oct 3–4 · 5:00–6:30 pm
Sand, jetty & open sky. The season's beachy, early-fall finale.
Parking: Free — Westport's paid-parking season ends Sept 30, so these October dates are open to everyone, no beach emblem needed.
Extended 40-minute sessions for larger families: $595, limited to two per evening. Weather backup is the following evening (or the next scheduled date), same times. Deposits transfer to any date and never expire. Private online gallery and print release included.
Two steps and you're done. Times that are already taken won't show up — what you see is what's open.
Your time slot is held for 24 hours after booking. Send the deposit to confirm it — put your name + session date in the Venmo note. Balance ($225) is due day-of.
Pay $125 on Venmo →or search @Justinw84 in the Venmo app
Deposits transfer to any date and never expire. If your time isn't confirmed within 24 hours, it reopens to the next family — no hard feelings, it just keeps things fair.
Can't make these dates or slots are gone? Email winwayfamily@gmail.com to join the November holiday-card mini waitlist — those dates go to the list first.