Holiday Stroll

December 4^th & 5^th 

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 2:00 PM. At 5:00 PM, we’ll kick off the Light Up Rowayton countdown, with school choirs before and after the lighting The Cocktail contest returns at the Firehouse with local favorites going head-to-head. We’re also turning up the energy with a holiday beer garden running through early evening. Post Parties will continue the fun on Rowayton Ave.
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Santa's Big Arrival

This year, Santa arrives by boat at 11:00 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 Bounces House at the park, write a letter to Santa, stop by for milk and cookies, or visit the historic trains in the Museum.

Road Closures & Parking

Rowayton Ave will be closed from 2:00 PM – 8:00 PM between Witch and McKinley. The Witch Lane lot will be open. You can also  plan to park at Rowayton Elementary School or the Rowayton Train Station.

Holiday Stroll Day #1: December 4th
6:00 PM – 8:30 PM

Kick off the Holiday Stroll weekend with the second annual Holiday Bike Crawl. Riders will make festive stops along the route—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. Brian McMahon Choir will bring the music. Places to gather, celebrate, and view the Bike riders will be all over Lower Rowayton Ave.

Holiday Stroll Day #2: Saturday, December 5th
10:30 AM – 6:30 PM

‍This year, ‍Santa arrives by boat at 11:00 AM at Pinkney Park! Watch parties start at 10:30 AM. He’ll spend about two hours at the park taking photos. No official photographer; bring your phone and snap your own pictures.

Pictures With Santa & Toy Drive

‍This year, Santa arrives by boat at 11:00 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. Please bring an unwrapped toy when visiting the Park or the Fire Station for the Toy Drive. We will provide a link to purchase toys for the Carver Foundation (ages 0–13).

Holiday Market

Rowayton Ave will close at 2:00 PM, and will be transformed with decorations, holiday themes, and treats from our merchants!
The Holiday Market at Pinkney Park opens 11.00 PM and runs until 6:00 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.

Holiday Lights & Music

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 and Roton Middle School will sing before and after the trees light up.

12th Annual Eggnog Contest
2:30 PM - 4:30PM

The eggnog contest has been broadened to festive holiday cocktails at  Rowayton Fire House! Local favorites go head-to-head to see who makes the best holiday cocktail in town. Come taste the contenders. 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