The RCA Holiday Stroll is stepping it up this year with fresh experiences across town. Santa’s making a bigger entrance than ever—arriving by boat at Pinkney Park before spending two hours taking photos with families. The Holiday Market expands with more vendors and a full-day schedule paired with the Gardeners Christmas Market right next door. Rowayton’s merchants are adding new themed setups, tree décor, and special treats that bring extra energy to Rowayton Ave once the road closes at 3:00 PM. At 5:00 PM, we’ll kick off the Light Up Rowayton countdown, followed by Symphonic Bodega. The eggnog contest returns at the Firehouse with local favorites going head-to-head. We’re also turning up the energy with a holiday beer garden that will run through the evening.
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This year, Santa arrives by boat at 11:45 AM at Pinkney Park! He’ll spend about two hours at the park taking photos. No official photographer—bring your phone and snap your own pictures. Before or after your Santa photo, kids can head to the Holiday Bounce House at the park.
Rowayton Ave will be closed from 3:00 PM – 8:00 PM between Witch and McKinley. The Witch Lane lot will be closed. Please plan to park at Rowayton Elementary School or the Rowayton Train Station.
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Kick off the Holiday Stroll weekend with the inaugural Holiday Bike Crawl, starting at Pinkney Park. Riders will make festive stops along the route — including The Bait Shop, Bell Island, Lower Highland Avenue, and finishing at the Community Center. Each stop will feature fun, community spirit, and plenty of holiday cheer. All participants are encouraged to decorate their bikes with lights to keep the ride bright and merry. It’s a great way to see friends, visit local spots, and start the weekend’s celebration.
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This year, Santa arrives by boat at 11:45 AM at Pinkney Park! He’ll spend about two hours at the park taking photos. No official photographer, bring your phone and snap your own pictures.
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This year, Santa arrives by boat at 11:45 AM at Pinkney Park! He’ll spend about two hours at the park taking photos. No official photographer, bring your phone and snap your own pictures. Before or after your Santa photo, kids can head to the Holiday Bounce House at the park. Santa begins his annual Toy Drive at 3:00 PM at Pinkney Park. We will provide a link purchase toys for the Carver Foundation (ages 0–13).
• Pinkney Park @ 3:00 PM
• Crest & Ridgewood @ 3:10 PM
• Train Station @ 3:25 PM
• South Beach @ 3:40 PM
• Brendan's 101 @ 3:50 PM
• Firehouse @ 4:00 PM
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Rowayton Ave will close at 3:00 PM, and will be transformed with decorations, holiday themes, and treats from our merchants!
The Holiday Market at Pinkney Park opens 12:00 PM and runs until 8:00 PM. Vendors will be announced in the days leading to the event.
The Gardener’s Christmas Market will also be in Pinkney Park and open all day.
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Lights go on at 5:00 PM. Santa leaves the Firehouse at 4:45 PM and walks to Pinkney. Join the walk and follow him into the park for Light Up Rowayton. Rowayton Elementary Carolers Sing at Pinkey at 5:15 PM followed by live music from Symphonic Bodega. The Brien McMahon Honors Choir will also be singing on Rowayton Ave at 5:00 PM.
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The eggnog contest returns to the Rowayton Fire House! Local favorites go head-to-head to see who makes the best holiday nog in town. Come taste the contenders, cast your vote, and help crown Rowayton's eggnog champion. It's one of the most fun traditions of the day.
Mark your calendars for an unforgettable start to the holiday season in Rowayton! For more information on the Holiday Stroll, contact info@rowaytoncivic.org
The River Ramble live auction begins at 1:30 PM!
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The River Ramble silent auction begins at 11 AM and closes at 3 PM!
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