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! Note: Items expire after one year.
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The River Ramble silent auction begins at 11 AM and closes at 2:45 PM!
Dine at your favorite local restaurants using gift cards from:
• Rowayton Seafood
• Sails
• Lykos Taverna
• Ardens
• Crust Issues
• 1020 Post
• L’Ostal
• Molto
• Rowayton Pizza
• Raphael’s Bakery
Plan a party:
• 314 Beer Garden
• Space Cat Brewery
• Four Forks Catering
• Platform tennis hut, with wine from Rowayton Wine and food from Palmers
• Manicure party at Posh
Create family memories:
• Rent a boat and captain from REX Marina Boat Club
• Photo shoot with Ben Larabee
• Laugh at the NY comedy club
• Shakespeare on the Sound
• Tennis lessons at Roton Point
• Rowayton Library children’s Gala
• Ride the Fire Truck to school
Find beautiful gifts:
• Chou Chou
• Mahjong lessons and mat from Five Mile Mahj
• Half-time Beer samplers
• Concert tickets at the Capitol Theatre
Secure awesome services:
• JKB professional organizing
• College counseling with Dr. Steve at Spark Your College Story
• College counseling Gina Bandini
• Career counseling with Karen Elders
• Memberships at Equinox
• Guest Passes at GritNinja
• Membership at Carozza Fitness
• Membership Spring Pilates
• Somatic Therapy session
• CKC salon cut, color or Keratin
• Dog training and walking with Bark Patrol
Make sure you're part of every future RCA event:
• 2027 Porch Fest tickets
• Comedy Night table
• Reserved table for the summer concert series
• July 4th parking and table for 2027 Fireworks
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