The first arrival of Rowayton's December comes by water. At 11 a.m. on Saturday, December 5, Santa comes up the Five Mile River by boat and lands at Pinkney Park. Watch parties line the river starting at 10:30. The day's centerpiece happens on foot. At 4:45 p.m. he leaves the Firehouse, walks to Pinkney, and the trees go on at 5:00.
Around those two moments, the Rowayton Civic Association's Holiday Stroll moves from the water to the park to Rowayton Avenue on a clock that barely changes from hour to hour. Several other groups have set their own schedules to match it. The Rowayton Gardeners, the Rowayton Arts Center and the Friday night bike riders all point at the same weekend. As a result, most of the village's holiday calendar falls into the stretch from Friday's 6:30 p.m. bike parade to Saturday's 7 p.m. close, a little over 24 hours.
Friday Night Opens It
The RCA describes this year's Stroll as "bigger and better" and spreads it over two days, December 4 and 5. Friday is the second annual Holiday Bike Parade, from 6:30 to 8:30 p.m. Riders are encouraged to decorate their bikes with lights, and spots to gather and watch are spread along lower Rowayton Ave.
Earlier that Friday, the Rowayton Arts Center at 145 Rowayton Avenue opens its Holiday Gift Show. Friday's opening-day hours are noon to 5 p.m., so the gallery closes before the parade starts. If you want to browse the gift show before the Saturday crowds arrive, Friday afternoon is the time to go.
The Saturday Clock
Saturday runs from 10:30 a.m. to 7 p.m. Here is how the day breaks down, using the times the organizers have posted:
| Time | What happens | Where |
|---|---|---|
| 10:30 a.m. | Watch parties begin along the river | Five Mile River |
| 11:00 a.m. | Santa arrives by boat, about two hours of photos | Pinkney Park |
| 11:00 a.m. | Gardeners Christmas Market opens, runs to 7 p.m. | Pinkney Park |
| 2:00 p.m. | Rowayton Ave closes between Witch and McKinley | Lower Rowayton Ave |
| 2:30 to 4:30 p.m. | Holiday cocktail tasting, 13th Annual Eggnog Contest | Rowayton Fire House |
| 4:45 p.m. | Santa leaves the Firehouse and walks to Pinkney | Rowayton Ave |
| 5:00 p.m. | Light Up Rowayton, with Rowayton Elementary carolers | Pinkney Park |
| 7:00 p.m. | Markets close, Rowayton Ave reopens | Pinkney Park and Rowayton Ave |
In the morning, the day centers on the park. The RCA is not hiring an official photographer, so families take their own Santa photos on their phones. Kids can also go to the Holiday Bounce House, write a letter to Santa, have milk and cookies, or ride the mechanical reindeer.
The Gardeners Christmas Market sits next to the RCA's Holiday Market in Pinkney Park. It sells handcrafted holiday wreaths and arrangements and gifts, holds a silent auction of gifts, experiences and local items, and pours complimentary Prosecco. The Gardeners' main listing gives 11 a.m. to 7 p.m. at Pinkney Park. A second event card lower on the same page says noon to 8 p.m. at the Community Center, so check with the Gardeners before you plan around a specific hour. The RCA's page prints the Holiday Market's opening as "11.00 PM," and the Gardeners' 11 a.m. start for their market in the same park is the more likely reading.
Why 2 p.m. Matters Most
The day changes at 2 p.m. That's when Rowayton Ave closes to cars between Witch and McKinley. The RCA says merchants will add decorations, holiday themes and treats along the closed stretch. Half an hour later, the Eggnog Contest begins at the Rowayton Fire House at 136 Rowayton Avenue. In its 13th year, the contest has widened to festive holiday cocktails, and tasting runs from 2:30 to 4:30.
The tasting ends 15 minutes before Santa leaves that same building for the park. People who stay at the Firehouse until the end of the tasting can walk behind him straight into Light Up Rowayton. The RCA invites people to join that walk and follow him into Pinkney, where Rowayton Elementary carolers sing before the trees are lit. The RCA also lists a holiday beer garden open through early evening and post parties continuing on Rowayton Ave.
The closure also determines where to park. The RCA lists three options:
- The Witch Lane lot, which stays open
- Rowayton Elementary School
- Rowayton Train Station
The Gardeners also mention parking at Old School Field. If you drive in for the morning boat arrival, you'll be parked before the 2 p.m. closure. If you drive in after 2, expect to walk in from one of the outer lots.
Bring an unwrapped toy. The Mike Barbis Toy Drive collects at both the park and the Fire Station, and the RCA says it will share a link for buying toys for the Carver Foundation, which serves children ages 0 to 13.
The Arts Center Matches Its Hours to the Stroll
The Rowayton Arts Center's regular Saturday gallery hours are 10 a.m. to 1 p.m., and it's open Tuesday through Friday from noon to 5. For the Holiday Gift Show, Saturdays stretch to 10 a.m. to 5 p.m., Sundays open from noon to 5, and the gallery stays closed on Mondays. On Stroll Saturday, December 5, it stays open from 10 a.m. to 7 p.m. That's six hours longer than a normal Saturday, and it closes when the markets in Pinkney Park close. Sunday, December 6, has added hours from noon to 5 as well.
The show runs December 4 through 24. On Christmas Eve it's open from 10 a.m. to 2 p.m., the last chance to pick up a gift there. Its posted materials list an opening day, not a separate reception. If you're looking for an evening opening, the Center's Winter Small Works Show holds its reception on Sunday, November 22, from 4 to 6 p.m.
The Weeks Around the Stroll
From Thursday, October 29, the Stroll is about five weeks out. The calendar between now and then, and the weeks after, is lighter and runs on a slower pace.
- November 1: Bayley Beach, reached by the drive at 11 Pine Point Road, begins its off-season pet period. The 6th Taxing District's Bayley Beach rules allow pets in the park from November 1 through March 31. The park is open year-round, weather permitting, and the district says off-season hours will be posted.
- Through November 14: The Rowayton Arts Center's Autumn Juried Show 2026 stays up. It opened October 18.
- November 22: Winter Small Works opening reception at the Arts Center, 4 to 6 p.m.
- November 26: The RCA Turkey Trot on Thanksgiving morning starts at 9 a.m. in front of the Rowayton Community Center, 33 Highland Avenue. Bib pickup opens at 7:45 and check-in is at 8:30.
- December 4 and 5: The Holiday Stroll.
- December 11: Shakespeare on the Sound presents a staged-reading benefit of "A Christmas Carol" at 7 p.m. in the United Church of Rowayton Community Room, 210 Rowayton Avenue.
- December 24: The Holiday Gift Show closes at 2 p.m.
The Turkey Trot and the Stroll both belong to the RCA, and they fall eight days apart. Thanksgiving morning begins at the Community Center on Highland Avenue, and the next big RCA event moves to Rowayton Ave and the river. The December 11 reading comes six days after the Stroll and is held at 210 Rowayton Avenue, on the same street as the Arts Center and the Fire House.
Still to Be Announced
Some parts of the Saturday program haven't been named yet. The RCA says Holiday Market vendors will be announced in the days before the event. It describes the cocktail contest as "local favorites" competing but hasn't listed the entrants. It also hasn't posted the beer garden's location or the post-party venues. Check the RCA's Holiday Stroll page during Thanksgiving week for those details, and check the Rowayton Gardeners for the final market hours.
The Stroll weekend shows how much of Rowayton's appeal is tied to a few blocks of Rowayton Avenue and the park on the river. If you'd like to know how your home's location relative to that stretch affects what it's worth today, Joshua Weisman can prepare a Free Home Valuation based on current Rowayton sales.
