Golden light, sweater weather, and everyone in one frame. Twenty unhurried minutes at the prettiest fall spots across Fairfield County — beaches, foliage, farms & village greens. Ten fully edited images in a private gallery within one week. Perfect for holiday cards, grandparents, and the mantel — $300 a session, capped at six families an evening, so book early.
Westport
Sat, Oct 3 · 5:00–6:30 pm
Sand, jetty & open sky. The season's beachy kickoff.
Parking: Free — Westport's paid-parking season ends Sept 30, so this date is open to everyone, no beach emblem needed.
Fairfield · village & shoreline
Sun, Oct 4 · 5:00–6:15 pm
Historic village greens and the harbor's edge at dusk.
Trumbull · Residents only
Fri, Oct 9 · 5:00–6:15 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 date is reserved for Trumbull families with a park sticker.
Fairfield · fall foliage
Sat, Oct 17 · 4:45–6:00 pm
Peak foliage mirrored off the water. The most colorful night of the season.
Shelton · river & woods
Sun, Oct 18 · 4:45–6:00 pm
Housatonic river bends and tall pines in full fall color.
Parking: Free for CT-registered vehicles (state park, Passport to the Parks). Out-of-state plates pay a small day-pass at the gate.
Great Hollow Lake · Monroe
Fri, Oct 23 · 4:40–5:50 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. Free lakeside lot.
Trumbull · Residents only
Sat, Oct 24 · 4:30–5:45 pm
Ponds, a stone bridge & manicured fields. Trumbull's prettiest park.
Trumbull residents only: a valid Trumbull park sticker is required to park (enforced year-round). This date is reserved for Trumbull families with a park sticker.
Wilton · barns & open fields
Sun, Oct 25 · 4:30–5:45 pm
Working-farm barns and golden pastures. Pure New England fall.
Weston · woodland trails
Fri, Oct 30 · 4:25–5:35 pm
Quiet woodland trails deep in fall color.
Parking: Free, but the lot is small and fills fast — please arrive a few minutes early.
State Park · Westport · late-fall marsh grass
Sat, Nov 7 · 3:45–4:45 pm
Marsh grass gone gold with soft shoreline light.
Parking: Free for CT-registered vehicles (state park, Passport to the Parks). Out-of-state plates pay a small day-pass at the gate.
Westport · open meadow
Sun, Nov 8 · 3:45–4:45 pm
Open meadow and big-sky light to close out the season.
Parking: Free on-site lot (25 Rte-136), open to all — no permit needed.
Weather backup is the next scheduled evening, same times. Deposits transfer to any date and never expire. Private online gallery and print release included. The exact meeting spot and parking details are sent after you book — and the two Trumbull dates (Old Mine & Twin Brooks) require a Trumbull park sticker.
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 ($175) 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.
Sold out or need a different date? Email winwayfamily@gmail.com to join the waitlist — cancellations and any added dates go to the list first.