In 2023, the Rowayton Gardeners held their Christmas Market at the Potting Shed at 33 Highland Avenue. It ran from 9 a.m. to 1 p.m. and sold wreaths, centerpieces, plum pudding, mini trees, ornaments, and silent auction items, all within a few steps of the library. Last December the same market moved to Pinkney Park at 177 Rowayton Avenue, where it joined the Rowayton Civic Association for the first Rowayton Holiday Stroll on Saturday, December 6, starting at noon.
This year the Stroll fills two days. It opens Friday evening, December 4, and runs Saturday, December 5, from 10:30 a.m. to 7 p.m. Its focal point has moved too. The village's holiday season now centers on the riverbank at Pinkney Park and the lower stretch of Rowayton Avenue, with Highland Avenue up the hill.
From Highland Avenue to the river
The Rowayton Civic Association's Holiday Stroll page says outright that the event is "stepping it up this year, bigger and better." The details back that up. There are more Holiday Market vendors and a full-day schedule. The Gardeners Christmas Market is set up next to it in Pinkney Park and open all day. Merchants along Rowayton Avenue are adding decorations and treats. A holiday beer garden runs into the early evening.
The Gardeners market is one of the clearest measures of the change. It used to be a four-hour morning sale on Highland Avenue. Now it is one part of a day that runs along the water. The Rowayton Gardeners call it their fundraising holiday event. The proceeds support the club's mission of promoting conservation, maintaining public spaces, and introducing children to growing things. Their 2025 listing on Norwalk Patch promised designer-quality wreaths and centerpieces, one-of-a-kind gifts, plum puddings, mini trees, ornaments, and a silent auction. The tables have moved, but they still offer the same things. If wreaths are what you are after, shop earlier in the day rather than at dusk.
Highland Avenue still has its own event. It comes first, on Thanksgiving morning.
Thanksgiving morning still starts at 33 Highland
The RCA's annual Turkey Trot is Thursday, November 26. It includes a 5K and the Kids' 1 Mile Gobble Gallop. Bib pickup opens at 7:45 a.m., runners gather near the library for check-in at 8:30, and the race starts at 9 a.m. in front of the Rowayton Community Center at 33 Highland Avenue. Here are a few details to know before race morning:
- Parking: Graham Capital, 40 Highland Avenue, across the street from the Community Center.
- Timing: The start uses chip transponders, so your time begins when you cross the line. There's no need to crowd forward at the horn. Gobble Gallop runners line up at the back.
- Bibs: Race-day pickup is not guaranteed, so the RCA recommends picking up bibs ahead of time. You can also collect them for family and friends. One-mile runners do not need bibs.
- Dress code: Costumes and turkey hats are encouraged, and strollers are welcome.
The RCA notes another record turnout and asks everyone to arrive at least 15 minutes early. If you plan to stop by the library that week, check its schedule first. Rowayton Library closes at 2 p.m. on Wednesday, November 25, and stays closed on Thanksgiving Day and Black Friday.
The Rowayton Arts Center opens the season early
The Rowayton Arts Center gets to December ahead of everyone else. Its Winter Small Works Juried Show runs from November 22 through December 24, with an opening reception on Sunday, November 22, from 4 to 6 p.m. Sandra Pelletier is the juror. The Holiday Gift Show opens December 4, the same Friday as the bike parade, and runs through December 24 at the gallery at 145 Rowayton Avenue. Both shows are on the avenue, so the gallery is an easy stop between Santa's arrival and the light-up.
Friday night, December 4
The weekend begins with the second annual Holiday Bike Parade, from 6:30 to 8:30 p.m. The RCA encourages riders to decorate their bikes with lights. Spectators can gather and watch from spots all along lower Rowayton Avenue. Last year's Stroll began Saturday at noon, so the Friday opener is new as of this weekend.
Saturday, December 5, in order
Saturday has more scheduled times than most residents will keep track of. In order, according to the RCA's schedule:
- 10:30 a.m. Watch parties start along the Five Mile River for Santa's arrival.
- 11 a.m. Santa arrives by boat at Pinkney Park and stays about two hours for photos. There is no official photographer, so bring your own phone. Kids can also visit the Holiday Bounce House, write letters to Santa, have milk and cookies, and ride the mechanical reindeer.
- All day The Holiday Market and the Gardeners Christmas Market are both in Pinkney Park. The Holiday Market runs until 7 p.m.
- 2 p.m. Rowayton Avenue closes to cars between Witch Lane and McKinley Street and fills with decorations and treats from local merchants.
- 2:30 to 4:30 p.m. The 13th annual eggnog contest takes place at the Rowayton Fire House. This year it is open to all festive holiday cocktails, and local favorites compete for the best one in town.
- 4:45 p.m. Santa leaves the Firehouse on foot and walks to Pinkney Park. Anyone can join the walk.
- 5 p.m. Light Up Rowayton. Carolers from Rowayton Elementary sing before the trees are lit.
- 7 p.m. Rowayton Avenue reopens to cars. After-parties continue on the avenue.
The schedule has two anchors, the Firehouse and the park, and the day moves back and forth between them. The cocktail contest is at the Firehouse in mid-afternoon. At 4:45, Santa leads the crowd from the Firehouse to the trees in Pinkney Park. Those 15 minutes are the one time the whole day moves in the same direction at once. If you only have part of the afternoon, aim to be at the Firehouse a little before 4:45 and walk down with everyone else.
Getting there and parking
The avenue closes at 2 p.m., and the day's events cluster in the late afternoon, so arriving after lunch takes some planning. The RCA lists three places to park:
- the Witch Lane lot, which stays open
- Rowayton Elementary School
- the Rowayton Train Station
If you come for Santa at 11 and stay through the 5 o'clock lighting, you will be there for six hours. The restaurants along the avenue can fill some of that time. Rowayton Seafood runs both its restaurant and its market at 89 Rowayton Avenue. Lykos Taverna, Ardens, Crust Issues, Rowayton Pizza, and Raphael's Bakery all donated gift cards to the RCA's River Ramble auction this year, and the shops Chou Chou and Posh contributed items as well.
Bring an unwrapped toy
The Stroll also runs a toy drive for another part of Norwalk. Visitors to Pinkney Park or the Fire Station are asked to bring an unwrapped toy for the Mike Barbis Toy Drive, which benefits children ages 0 to 13 at the Carver Foundation. The RCA will also share a link to buy toys online. The Carver Foundation explains that the Rowayton Fire Department and the RCA deliver the gifts together. Joan DeRegt co-founded the tradition. It now carries the name of the late Mike Barbis, a former Rowayton commissioner and longtime Carver advocate. Gifts have included toys, books, sporting equipment, and gift cards.
After the lights go on
The RAC Holiday Gift Show and the Winter Small Works show both stay up through Christmas Eve, so the gallery at 145 Rowayton Avenue keeps its holiday shows open well after the Stroll weekend ends. Rowayton Library closes Thursday, December 24 through Saturday, December 26. If you were counting on the library for something for the kids that week, plan around those days.
If you have family coming for the Stroll weekend and want help planning around the river and the road closure, or if a guest at the light-up starts asking about life in Rowayton, Rachel Walsh is happy to share what she knows about the village. Book an appointment whenever it suits you, before or after the holidays.