The Rowayton Civic Association has planned this year's Holiday Stroll as a day-long event. Santa arrives by boat at Pinkney Park at 11 a.m. on Saturday, December 5. The tree lights don't go on until 5 p.m., and the hours in between are full of events. The RCA describes the change plainly. The Holiday Market "expands with more vendors and a full-day schedule," it sits next to the Rowayton Gardeners Christmas Market, and a holiday beer garden runs into the early evening.
So the tree lighting is now how the day ends. On Saturday, the time to plan around is 2 p.m., when Rowayton Avenue closes to cars between Witch Lane and McKinley Street. Every event before then is easy to get to by car, and every event after it is easier on foot. The rest of the season, from mid-November to mid-December, builds up to this weekend in Pinkney Park.
The run-up starts November 17
The weeks before the Stroll fill in gradually.
- Tuesday, November 17. The Rowayton Library calendar has a Noir-vember Movie Matinee from 3 to 5 p.m. You need to register. It's followed by the Silent Book Club from 6 to 8 p.m.
- Sunday, November 22. The Rowayton Arts Center opens its Winter Small Works Juried Show with a reception from 4 to 6 p.m. Sandra Pelletier is the juror and Best in Show wins $250. The work on the walls is deliberately not holiday-themed. The show runs through December 24.
- Thursday, November 26. The RCA's Turkey Trot starts at 9 a.m. in front of the Rowayton Community Center, 33 Highland Avenue. There's a 5K and a 1-mile Gobble Gallop for kids.
The Turkey Trot is the only big event of the season that isn't in Pinkney Park, and its logistics are the opposite of the Stroll's. Bib pickup opens at 7:45 a.m. and check-in is at 8:30 near the library. The RCA does not guarantee bibs on race day and suggests picking them up ahead of time. You can run without a bib, but you won't get a time. Timing chips are read at the start line, so the RCA asks runners not to crowd forward when the horn sounds. Gobble Gallop runners should line up at the back. Because turnout has been at record levels, organizers suggest arriving at least 15 minutes early. Parking is at Graham Capital, 40 Highland Avenue, across the street, and spectators come free.
Friday night happens on Lower Rowayton Avenue
The Stroll weekend starts Friday, December 4, from 6:30 to 8:30 p.m. with the second annual Holiday Bike Parade. Riders are asked to decorate their bikes with lights. The RCA says places to gather and watch will be "all over Lower Rowayton Ave."
The Rowayton Arts Center's Holiday Gift Show also opens December 4 and runs through December 24. It sells ornaments, jewelry, pottery and ceramics, candles, wooden objects, knitted and crocheted pieces, and fiber art. Exhibiting members also sell original cards and small prints. Since the gift show opens the same day as the Stroll, the village's three holiday shopping options are all available that weekend: the RAC show, the RCA market and the Gardeners' market.
Saturday, December 5, by the clock
This is how the RCA and the Rowayton Gardeners have scheduled the day:
- 10:30 a.m. The Stroll officially opens. Watch parties gather 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. The Rowayton Gardeners Christmas Market opens in the park at the same time and runs until 7 p.m.
- Around 1 p.m. Santa's photo window in the park ends.
- 2 p.m. Rowayton Avenue closes between Witch and McKinley, and the merchants' decorations and treats take over the street.
- 2:30 to 4:30 p.m. The holiday cocktail contest runs at the Rowayton Fire House.
- 4:45 p.m. Santa leaves the Firehouse and walks to Pinkney Park, and anyone can walk along.
- 5 p.m. Rowayton Elementary carolers sing, then the park lights up for Light Up Rowayton.
- 7 p.m. Both markets close and Rowayton Avenue reopens. The RCA says Post Parties will keep going on Rowayton Ave.
The middle of the day is now the busiest part. Between Santa's photo window and the lighting there are several hours, and the RCA's expanded schedule fills them with the markets, the beer garden and the cocktail contest.
The cocktail contest is in its 13th year
The Fire House contest began as the eggnog contest. The RCA counts this year as the 13th, and it has opened the competition to any festive holiday cocktail, with local favorites competing for best in town. Tasting runs from 2:30 to 4:30 p.m.
That timing puts the contest right after the road closes and ends it just before Santa leaves the same building at 4:45. If you're at the Fire House at the end of the tasting, you're already at the start of the walk to the lighting. On a day with this much going on, that's the most efficient handoff on the schedule.
Where the cars go after 2 p.m.
The RCA lists three places to park for the afternoon:
- Witch Lane lot. It stays open during the closure.
- Rowayton Elementary School. It's the same school whose carolers sing before the lights go on.
- Rowayton train station.
The Gardeners point their market shoppers to Old School Field. Morning visitors who come for Santa and the markets can leave before the road closes. If you're staying for the lighting, it's easiest to park in one of the listed lots from the start so you don't have to move your car at 2.
What to bring to Pinkney Park
Bring your phone. The RCA says there is no official photographer for the Santa photos, so families take their own. Kids can also go to the Holiday Bounce House, write a letter to Santa, have milk and cookies, or ride the mechanical reindeer.
Bring an unwrapped toy too. The Mike Barbis Toy Drive collects toys at both the park and the Fire Station. The RCA also plans to share a link for buying toys for the Carver Foundation, for ages 0 to 13.
At the Gardeners' tables, members sell wreaths and arrangements they make themselves, along with holiday gifts and a silent auction of gifts, experiences and local favorites. Prosecco is complimentary while you shop. Proceeds support the club's beautification, conservation, education, outreach and scholarship work during the year. RCA Holiday Market vendors will be announced in the days before the event.
A week later, Pinkney Park again
The park hosts one more big evening before the season ends. The Rowayton Nativity Pageant takes place Saturday, December 12, from 6 to 7 p.m. Local performers and clergy tell the Nativity story with live music, and Rowayton pets join the pageant.
The RCA's annual Christmas tree sale comes right after the pageant weekend. It starts at 9:30 a.m. and trees are $45 each. To confirm the sale date, email the RCA at [email protected].
If you're planning dinner around any of these evenings, note that Pearl at 89 Rowayton Avenue has closed for the season and says it will be back in 2027. Rowayton Seafood, at the same address, lists weekly restaurant service and menus on its site.
Pinkney Park on December 5, with Santa's boat at the dock and the lights coming on at dusk, is the kind of scene that sticks with people about Rowayton. If you live within a walk of the park and the river and want to know what your home is worth this season, the Coastal Collective Team can walk you through it. Request Your Free Home Valuation.
