When does the holiday season actually start in Darien this year? By the town's own calendars, it starts Saturday, November 21, five days before Thanksgiving. It wraps up one week later, on Saturday, November 28. In between, the events move among three parts of town: Brookside Road, Heights Road and the Post Road downtown. The dates are easy to remember, but the hours on each day take more planning.
Here is the full week, in order:
- Saturday, Nov 21: Darien Nature Center Holiday Market, 10 a.m. to 2 p.m., and the Pop Shop Holiday Market at Darien Commons, 11 a.m. to 5 p.m.
- Monday, Nov 23: The Festival of Wreaths opens at the Nature Center, early bib pickup for the Turkey Trot begins at The Depot, and Darien Library shows Planes, Trains and Automobiles that evening.
- Tuesday, Nov 24: The last early bib pickup windows.
- Wednesday, Nov 25, 3 p.m.: Darien Library closes for Thanksgiving.
- Friday, Nov 27: The Overstuffed Turkey Trot in the morning, then the Lit Tree Lane Stroll when the library reopens that evening.
- Saturday, Nov 28: Spirit of the Season: Shop Small Business Saturday, 8 a.m. to 6 p.m.
The Two Markets Overlap for Three Hours on November 21
The Darien Nature Center Holiday Market runs from 10 a.m. to 2 p.m. at 120 Brookside Road. It's free, and you don't need to register. The Nature Center has already named several vendors:
- DoChéri Chocolate, European-inspired chocolates handcrafted in Darien
- Turtle Moon Health, a Wilton-based company selling honey, teas and natural wellness products
- Ceramics by Maggie Chow, nature-inspired handmade pottery
- The Perfect Stitch, handmade dog kerchiefs and accessories
- Noonday, jewelry and accessories handcrafted by women around the world
The same day on Heights Road, Darien Commons hosts the Pop Shop Holiday Market outside sweetgreen at 102 Heights Road, from 11 a.m. to 5 p.m. It's also free. The Darien Chamber of Commerce's listing describes apparel, handmade jewelry, home décor, self-care products, gifts and specialty goods, and it lists Darien Commons as a partner of Pop Shop Market CT.
Both markets are open from 11 a.m. to 2 p.m., so that's your window if you want to see both. Brookside closes earlier, at 2, so it makes sense to start there. Then head to Heights Road, where the Pop Shop vendors stay until 5.
The market is only the first Nature Center event of the week, and the next one also takes place on Brookside Road.
Brookside Road Stays Busy Through December 3
Two days after the market, the Nature Center opens its Festival of Wreaths. One-of-a-kind wreaths made by local artists, businesses and community members will be on display and open for bidding from November 23 through December 3, 10 a.m. to 5 p.m. The proceeds support Nature Center programming. A community reception and final bidding are set for Thursday, December 3, from 6 to 7:30 p.m.
Since the wreaths are up during the day, you can stop by any weekday morning of Thanksgiving week. The market is a single Saturday, but you have eleven days to see the wreaths and place a bid.
Heights Road Gets Busy Again Before Thanksgiving
The Pop Shop vendors pack up on Saturday, and on Monday, Heights Road fills up again for a different reason. The Depot, Darien's youth center at 25 Heights Road, is handing out early bibs for its 4th Annual Overstuffed Turkey Trot. Pickup hours are Monday, November 23, from noon to 2 p.m., and Tuesday, November 24, from 8:30 to 10:30 a.m. and again from 5 to 7 p.m.
Early pickup saves you a stop on race morning, and the Tuesday evening slot is the easiest one to fit around a workday. If you miss both days, bibs are also handed out on race day starting at 9 a.m.
Registration costs more the closer you get to the race. Adult entry was $45 through November 1. It's $50 from November 2 through 26 and $55 on race day, plus fees. Kids ages 6 to 12 pay $30, plus fees. As of this week, adults pay $50, and that price holds until Thanksgiving Day.
Monday evening has another option. Darien Library's November calendar lists a Monday Night Movie screening of Planes, Trains and Automobiles on November 23, from 6:30 to 8:30 p.m. Registration is required. The library's event page describes a story about a trip home for Thanksgiving, which makes it a fitting choice for the Monday before the holiday.
Friday Starts on the Cross-Country Trail and Ends at the Library
Most of this week's planning comes down to the day after Thanksgiving.
The morning belongs to the Turkey Trot on the Darien High School cross-country trail. A timed 1-mile walk/run starts at 10 a.m., and the 5K walk/run follows at 10:30. The Chamber's listing says last year's race drew more than 550 runners and included music, children's games and food, and all proceeds go to The Depot. The timing works well for families: kids can run the mile at 10, and the adults can still make the 5K start half an hour later.
The evening belongs to Darien Library at 1441 Post Road and its 4th Annual Lit Tree Lane Stroll, from 6:30 to 8 p.m. It's free. Community members, designers and local organizations decorate trees, each one inspired by a beloved book, and the evening includes festive music and refreshments.
The library's Thanksgiving hours shape that evening. The library closes at 3 p.m. on Wednesday, November 25, and stays closed until 6 p.m. on Friday, November 27. That means the doors open just 30 minutes before the stroll starts. You won't be able to drop off a book or pick up a hold Friday afternoon and then stay for the trees. The library is closed all day until 6, and the first chance to walk in is the stroll itself.
So Friday is split between a 10 a.m. start on one side of town and a 6:30 p.m. start on Post Road, with a free afternoon in between.
Saturday Moves Downtown
The week ends with the Chamber's Spirit of the Season: Shop Small Business Saturday on November 28, from 8 a.m. to 6 p.m. The Chamber says Darien businesses will offer deals along with one-of-a-kind products and services, and the downtown lamp posts will have holiday lights.
The hours are long. The 8 a.m. start makes it easy to shop before a weekend of leftovers and houseguests, and the 6 p.m. finish means the last hour of shopping happens after sunset, when the lamp-post lights are on.
If the Nature Center market on the 21st introduced you to a maker like DoChéri Chocolate, the following Saturday is the Chamber's day for shopping locally all across town. The two Saturdays bookend the week. One introduces local makers under one roof on Brookside Road, and the other spreads the shopping across downtown.
If you have guests coming for Thanksgiving week, this schedule makes it easy to show them around. The Nature Center wreaths are good for a weekday morning, the Friday trot works for the whole family, and the Lit Tree Lane Stroll fills Friday evening. I've lived next door in Wilton since 2002, and I enjoy helping neighbors plan around what's happening locally, whether that's a holiday week or something bigger. If this season has you wondering what your own home might be worth, Lovisa Wisdom can help. Get Your Instant Home Valuation, and I'm happy to follow up over coffee once the holiday rush settles.
