The holiday tree at Tilley Pond Park goes on at the end of a Saturday afternoon. It closes out three hours of cookie decorating, holiday crafts, an ice sculpture display and a small holiday market. Darien Parks & Recreation holds the event, called An Old Fashion Holiday, on Saturday, December 5, from 2 to 5 p.m. at 40 West Avenue. It is free and open to all ages.
In many towns the tree lighting starts the season. In Darien it comes last. By December 5, the Darien Nature Center's wreaths will have been on display for nearly two weeks, and their bidding will have closed two days earlier. Darien Library's book-themed trees will have had their opening night a week earlier. Two holiday markets will already have come and gone.
The calendar has one long-running display you can visit on almost any day, plus single-day events with fixed start times. The display opens two days after the first markets and gives you room to plan around it. Most of the single-day events fall on three Saturdays and the Friday after Thanksgiving, and two of those Saturdays pair events that hand off neatly from one to the next.
The Wreaths Set the Deadline
One display sets the pace for the season, and it doesn't need you there at a set hour.
The Darien Nature Center's Festival of Wreaths has one-of-a-kind wreaths made by local artists, crafters, businesses and other community members. They're auctioned to support the Nature Center's education programs. According to the Nature Center's festival page, the wreaths are on display and open for bidding from November 23 through December 3, ending with a reception and final bidding on December 3. The Darien Chamber of Commerce listing gives display hours of 10 a.m. to 5 p.m. at 120 Brookside Road and a reception from 6 to 7:30 p.m. that Thursday.
Darien Library's Lit Tree Lane Stroll comes four days into the wreath run. On one evening, Friday, November 27, the library hosts a stroll among book-inspired trees decorated by local artists and organizations.
| Event | Where | Starts | Ends | What closes it |
|---|---|---|---|---|
| Festival of Wreaths | Darien Nature Center, 120 Brookside Road | Monday, November 23 | Thursday, December 3 | Reception and final bidding |
| Lit Tree Lane Stroll | Darien Library, 1441 Post Road | Friday, November 27, 6:30 p.m. | Friday, November 27, 8 p.m. | End of the stroll |
The wreath festival runs 11 days and has a firm deadline for anyone who wants to bid. It is open before every other event on the calendar except the first market Saturday, and it closes two days before the tree lighting. If you plan to bid on a wreath, finish at Brookside Road by December 3.
Thanksgiving Friday Has Two Events, Eight Hours Apart
The busiest single day of the season is the Friday after Thanksgiving, not the holiday itself.
The morning belongs to The Darien Depot's Overstuffed Turkey Trot on the Darien High School cross-country trail at 80 High School Lane. Both RunSignup and The Depot list it for Friday, November 27, 2026, and The Depot pitches it as a way to work off Thanksgiving dinner the day after. The timed 1-mile walk/run starts at 10 a.m. and the 5K walk/run at 10:30 a.m. All proceeds go to The Depot, Darien's youth center.
What runners need to know, according to the race listings:
- Cost: Adults pay $50 plus fees from November 2 through 26 and $55 on race day. Children ages 6 to 12 pay $30 plus fees, and children 5 and under run free. Teams of five or more save $5 per adult runner.
- Bib pickup: Early pickup is at The Depot, 25 Heights Road, on Monday, November 23, from noon to 2 p.m., and Tuesday, November 24, from 8:30 to 10:30 a.m. and 5 to 7 p.m. Race-day pickup opens at 9 a.m.
- Rules: Dogs are not allowed on the Darien High School campus. Strollers are allowed only in the 1-mile event.
- Weather: The backup date is Saturday, November 28, and it will be used only if it snows.
The Chamber listing says last year's race drew more than 550 runners, along with music, children's games and food.
That evening, the Lit Tree Lane Stroll runs at the library from 6:30 to 8 p.m., with festive music, refreshments and a craft and scavenger hunt for children. It is free and needs no registration. The morning race and the evening stroll are eight hours apart, which leaves the afternoon open.
On Saturday, November 28, the Chamber's Shop Small Business Saturday runs from 8 a.m. to 6 p.m., with holiday lights on the downtown lamp posts. The Chamber's business directory lists the participating shops.
Two Saturdays, Each Built for Two Stops
The single-day markets fall on the Saturdays at either end of the season, and both days have room for two events.
Saturday, November 21, comes first. The Darien Nature Center Holiday Market runs from 10 a.m. to 2 p.m. at 120 Brookside Road. It features local businesses, artisans and gifts you won't find elsewhere. It is free, open to all, and needs no registration. At Noroton Heights, the Pop Shop Holiday Market at Darien Commons runs from 11 a.m. to 5 p.m. outside sweetgreen at 102 Heights Road. It is part of a series of artisan markets that Darien Commons hosts with Pop Shop Market, featuring independent makers selling apparel, handmade jewelry, home décor, self-care products and specialty goods. The two markets overlap from 11 to 2, and the Heights Road market stays open three hours after Brookside Road closes. A morning at the Nature Center and an afternoon at the Commons fits easily into one day, and the Commons restaurants can cover lunch or dinner.
Saturday, December 5, works the same way and ends with the tree. The Darien Community Association's Merry Meadowlands holiday market runs from 10 a.m. to 2 p.m. at 274 Middlesex Road. The DCA lists 40 selected vendors, admission is free, and purchases support the DCA's programs and properties. The Chamber listing adds that the Meadowlands house will be decorated for the season. Merry Meadowlands closes at 2 p.m., the same time An Old Fashion Holiday opens at Tilley Pond Park. It runs until 5 p.m. and ends with the tree lighting.
The two Saturdays fit together. November 21 is the first day for holiday shopping, and December 5 is the last day for it on the town calendar. Between them come the wreath bidding, the Thanksgiving Friday events and Small Business Saturday.
The Season in Order
- Saturday, November 21: The Darien Nature Center Holiday Market, 10 a.m. to 2 p.m., then the Pop Shop Holiday Market at Darien Commons, open until 5 p.m.
- Monday, November 23: The Festival of Wreaths opens for display and bidding at the Nature Center. Early Turkey Trot bib pickup starts at The Depot.
- Friday, November 27: The Overstuffed Turkey Trot at 10 and 10:30 a.m., then the Lit Tree Lane Stroll from 6:30 to 8 p.m.
- Saturday, November 28: Shop Small Business Saturday downtown, 8 a.m. to 6 p.m.
- Thursday, December 3: The Festival of Wreaths reception and final bidding, 6 to 7:30 p.m.
- Saturday, December 5: Merry Meadowlands at the DCA, 10 a.m. to 2 p.m., then An Old Fashion Holiday at Tilley Pond Park, 2 to 5 p.m., with the tree lighting at the close.
Six of the 15 days from November 21 through December 5 have something new on the calendar, and the wreaths are on view for 11 of them. Bidding on the wreaths closes on Thursday evening, December 3, and the tree at Tilley Pond Park is lit two days later.
When conversations at the wreath reception or on the Tilley Pond lawn turn to the year ahead, Serena Richards of CT Home Keys is glad to talk through what the coming season could mean for your Darien home. Request a Private Market Consultation whenever you're ready.
