The Rowayton Civic Association invites you to a full weekend of holiday fun as we kick off the season with lights, laughter, and community spirit.

Holiday Stroll Day #1
Friday, December 5th | 6:00 PM – 8:30 PM

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.

Bicycle Crawl
6:00 PM - 8:30 PM @ Pinkney Park
Sign Up Here

Holiday Stroll Day #2
Saturday, December 6th | 11:45 AM – 8:30 PM

Santa Arrives by boat
‍11:45 AM @ Pinkney Park

Photos with Santa
12:00 PM - 2:00 PM @ Pinkney Park Gazebo

Holiday Bounce House
12:00 PM - 2:30 PM @ Rowayton Avenue & Pinkney Park

Holiday Market
12:00 PM - 8:00 PM @ Pinkney Park

Rowayton Gardners Christmas Market
12:00 PM @  Pinkney Park

Mike Barbis Santa Toy Drive
3:00 PM - 4:00 PM @ (See Santa Run Route Below)

Merchant Displays & Activities
4:00 PM - 8:00 PM @ Rowayton Avenue

10th Annual Eggnog Contest
4:00 PM - 8:00 PM @ Rowayton Ave
Sign Up Here

Light Up Rowayton (Santa Arrives)
5:00 PM @ Pinkney Park

Holiday Beer Garden
5:00 PM - 8:30 PM @ Pinkney Park

Live Music
5:15 PM - 8:00 PM @ Pinkney Park