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Address
15 Corbin Dr
Darien, CT 06820 -
Randy Musiker
Darien lights its holiday tree at Tilley Pond Park on Saturday, December 5. By then, most of the season's other dates will already have happened. The markets, the Turkey Trot bib pickup and the fundraising run for The Depot are spread over the two weeks around Thanksgiving, and much of that activity sits on one short stretch of Heights Road in Noroton Heights.
Darien Commons is at 102 Heights Road. The Depot is at 25 Heights Road. Magnolia, one of the best-known names at the Commons, is at 134 Heights Road. If you plan November around that strip and treat Tilley Pond as the final stop, the calendar makes sense.
The first big holiday date is Saturday, November 21, and it has two markets in two parts of town.
The Darien Nature Center Holiday Market runs from 10 a.m. to 2 p.m. at 120 Brookside Road. Vendors are local artisans and crafters selling handcrafted, sustainable gifts, and the center also lists food and face painting.
The same day, Pop Shop Market sets up at Darien Commons, outside sweetgreen at 102 Heights Road, and admission is free. The listed hours don't agree. The Darien Chamber of Commerce listing says 11 a.m. to 5 p.m., and Pop Shop Market's own season page lists the "Holiday Pop Shop Darien" from 10 a.m. to 4 p.m.
Under either set of hours, one order works for both markets:
Going in the other direction is riskier. If you linger at the Commons into the early afternoon, the Nature Center market may be packing up by the time you arrive.
The Pop Shop market isn't a one-time holiday event. Pop Shop's 2026 season and the Chamber both list four dates at Darien Commons: August 22, September 19, October 17 and November 21. That makes the November market the last one of the season. Darien Commons is listed as the event's organizer, and Pop Shop Market curates the vendors.
Pop Shop Market has been running artisan markets since 2012, and it calls Darien Commons a new venue for its 2026 season. The market takes place outdoors in the Commons' main parking lot, with vendors in 10-by-10-foot spaces. The organizer lists the rain date as "TBD." If the forecast for November 21 looks wet, check with the organizer that morning.
The Chamber listing names these product categories:
Between the two markets, one November Saturday covers a lot of holiday shopping. The Nature Center focuses on handcrafted, sustainable gifts. The Pop Shop market leans toward style and home goods. Both are run by local organizations, not national chains.
The Pop Shop market sets up next to a full retail center, so the stops around it are as useful as the booths. The Darien Commons directory lists several places that suit a cold Saturday afternoon:
The directory marks Magnolia as "New," but it has been at the Commons longer than that suggests. Patch covered its ribbon-cutting at 134 Heights Road in December 2024, so this will be its second holiday season in Darien.
Six days after the markets, Heights Road gets busy again for a different reason. The Darien Depot Overstuffed Turkey Trot takes place on Friday, November 27, the day after Thanksgiving, on the Darien High School cross-country trail. Proceeds go to The Depot.
The race registration page lists two starts:
Bib pickup is where Heights Road comes in again. Early pickup is at The Depot, 25 Heights Road, during three windows:
Race-day pickup opens at 9 a.m. If you're hosting Thanksgiving, the Tuesday evening window fits neatly with a grocery run. If you'd rather keep Tuesday free, the 9 a.m. Friday pickup also works, though it adds a stop on race morning.
The two sources disagree on how long the morning lasts. The Depot's own calendar lists the event from 9 to 11 a.m., while the RunSignup event listing gives the 5K an end time of noon. Plan around the start times, and if you need to be somewhere afterward, leave room until midday.
Two weeks after the November markets, the season's main town event takes place at Tilley Pond Park. Darien Parks & Recreation's listing describes it this way:
"This FREE, all-ages event will feature cookie decorating, holiday crafts, an ice sculpture display, a holiday market, and more seasonal activities to enjoy with family and friends."
An Old Fashion Holiday runs from 2 to 5 p.m. on Saturday, December 5, and ends with the lighting of the town's holiday tree. The town gives the address as 40 West Avenue, and the same listing's location field says Lakeside Avenue and West Avenue, so either one will get you to the park.
The event includes a holiday market, which means Darien has three markets this season in three locations: Brookside Road and Heights Road on November 21, then Tilley Pond on December 5. If you skip the November markets, the Tilley Pond market is your last chance at an in-town market this season. Because the tree lighting closes the afternoon, the best time to arrive is between late afternoon and 5 p.m.
The date moves a little each year. Patch reported that the 2025 event was held on Saturday, December 6, also from 2 to 5 p.m.
The weekend right after the Turkey Trot is the one open question. In 2025, Patch's coverage of the Spirit of the Season program listed a town-wide Holiday Lights and Shop Small Saturday on November 29. It also listed the annual Darien Sport Shop tree lighting on Sunday, November 30, from 4:30 to 5:30 p.m., with Santa arriving at 5 p.m. The Darien Chamber of Commerce, Darien Parks & Recreation and Darien Sport Shop organized that program together.
In 2026, that weekend is November 28 and 29. The 2026 versions of those events haven't been posted yet, so the Chamber's community calendar is the place to check.
If this calendar has you thinking about which side of Darien you'd like to be living in next December, Randy Musiker can walk you through the Noroton Heights side and the Tilley Pond side street by street. Let's talk about your next move. Contact Randy for a consultation.
Address
15 Corbin Dr
Darien, CT 06820
Randy Musiker