Most of South Windsor's holiday events this year fall on two Saturdays. On Saturday, Nov. 21, a craft fair opens at 9 a.m., the town's Winter Market follows at 10 a.m., and Dzen Tree Farm opens for the season the same day. Two weeks later, on Dec. 5, the First Congregational Church fair on Main Street wraps up at 2 p.m., and the tree lighting at Evergreen Walk begins three hours after that.
That makes both days fairly predictable. Each one has a natural order from morning to evening. If you miss the window for one event, there isn't a later date for it.
Saturday, Nov. 21 Starts at 9 a.m. on Nevers Road
Here's Nov. 21 in order:
- 9 a.m. The Holiday Hoopla Craft Fair opens at South Windsor High School, 161 Nevers Rd.
- 10 a.m. The South Windsor Winter Market opens at the Parks and Recreation Facility, 350 Foster St. It runs until 2 p.m.
- Same day Dzen Tree Farm opens for the 2026 season at 215 Barber Hill Road.
Holiday Hoopla is the biggest of the three. The Patch listing posted by SW Operation Graduation says more than 85 crafters and vendors will be there. All proceeds go to Operation Graduation, which organizers say keeps seniors safe on graduation night. That means every gift you buy there also funds a South Windsor tradition for the class of 2027.
The Winter Market opens an hour later and keeps shorter hours. The Winter Market announcement on Patch calls it the annual South Windsor Winter Market and gives the same 10 a.m. to 2 p.m. window. The South Windsor Parks and Recreation calendar lists it too, as the 2026 Winter Market. The market closes at 2 p.m., so the craft fair is the event with more flexible timing.
Of the three, only Dzen's opening is the start of a season and not a one-day event. The farm's own site gives Nov. 21 as opening day but doesn't post daily hours. For hours, call the farm at (860) 648-2233.
Dzen Charges One Price for Every Tree
Dzen Tree Farm posts one 2026 price for any size and any variety: $95 cash or check, or $100 by credit card. A flat price changes how you shop. The decision is about which tree fits your living room, because a taller fir costs the same as a shorter spruce. The $5 card difference is the only price choice you'll make.
The farm on Barber Hill Road also sells wreaths, tree stands, snacks and gifts at the Rockin' Reindeer Cafe. The site also invites visitors to see Santa's live reindeer as they get ready for Christmas Eve.
Opening on Nov. 21 puts Dzen a week ahead of Syme Family Farm at 72 Windsorville Road in Broad Brook. The Syme Family Farm Christmas page lists cut-your-own on three Friday-to-Sunday weekends, starting Nov. 27 and ending Dec. 13, at $87.68 including tax and the reservation fee. Its Christmas Barn is open the same days from 9 a.m. to 4 p.m. If you want a tree up before Thanksgiving, the South Windsor farm has the earlier opening.
Between the Saturdays, Sullivan Avenue Has Something New
Thanksgiving falls on Nov. 26, right between the two Saturdays, and a new bagel shop on Sullivan Avenue is open in that stretch.
CTbites' November 2026 roundup of Connecticut restaurant openings reports that family-owned Benson's Bagels has opened its third location at 1014 Sullivan Avenue. CTbites says the shop bakes more than 15 varieties of bagels every day, along with pancakes, coffee, tea, breakfast and lunch sandwiches, and smoothies. CTbites also suggests checking a new restaurant's own pages for current hours before you go.
Dec. 4 to 6 Runs From Main Street to The Green
The second Saturday actually starts the evening before. First Congregational Church of South Windsor holds its 79th Heritage Holiday Fair at 993 Main St. over three days, with free admission each day. On Saturday, Evergreen Walk holds its evening event once the church fair has closed.
| Day | First Church Heritage Holiday Fair, 993 Main St. | Evergreen Walk, The Green |
|---|---|---|
| Friday, Dec. 4 | 5 to 8 p.m. | |
| Saturday, Dec. 5 | 9 a.m. to 2 p.m. | Torchlight Parade and Tree Lighting, 5 to 7 p.m. |
| Sunday, Dec. 6 | 1 to 4 p.m. |
The town calendar listing for the Heritage Holiday Fair shows how the fair differs from the Nov. 21 craft fair. Along with crafts, it sells things for the house. The sample list includes homemade fudge, home-baked treats and candy, vintage and fashion jewelry, crochet, quilted and knit items, Rada cutlery, handmade ornaments, cemetery boxes, fresh greens arrangements and centerpieces, and artificial greens and wreaths. Fresh greens are one item that changes depending on which day you go. The Friday evening session is the earliest chance to buy them.
Three hours after the fair closes on Saturday, the Shops at Evergreen Walk start their annual Holiday Torchlight Parade and Tree Lighting on The Green. The schedule lists Santa arriving with the torchlight parade, a tree lighting with Santa and the South Windsor Fire Department, photos with Santa and a free gift for every child while supplies last. It also lists live holiday music, treats from the restaurants at Evergreen Walk, giveaways, and Renee DiNino as emcee.
That gives you a 9 a.m. start on Main Street and a 7 p.m. finish at Evergreen Walk, with the afternoon open for Dzen Tree Farm or Benson's Bagels in between. Since the free gifts run while supplies last, it helps to arrive near the 5 p.m. start.
Dec. 19 Brings the Library Into It
Later in the month, the South Windsor Public Library at 1550 Sullivan Avenue has a holiday program of its own. On Saturday, Dec. 19, the library's Edible Holiday Cookie Dough program runs from 2 to 3:30 p.m., and the listing names the Children's Program Room. All ages are welcome, children under five need a parent or guardian with them, and registration is required.
The library and Benson's Bagels are both on Sullivan Avenue, at 1550 and 1014. That makes Dec. 19 a natural day for both.
Here are the dates to put on your calendar: Nov. 21 for the craft fair, the Winter Market and Dzen's opening; Dec. 4 through 6 for the Heritage Holiday Fair; the evening of Dec. 5 for the Evergreen Walk tree lighting; and the afternoon of Dec. 19 at the library. Because the season is packed into so few days, missing one Saturday means missing several events at once.
If you're thinking about putting your house on the market after the holidays, these quieter weeks between the two Saturdays are a good time to find out where it stands. Cindy Muska can put together a free home valuation for your South Windsor house before the January rush. Call or text, and Cindy will work around your Saturdays.
