"There are usually about 20-30 gingerbread houses in the contest, they are down on entrants as they only have about 9 so far." That line from the draft minutes of Simsbury's Culture, Parks and Recreation Commission for its October 22, 2026 meeting summarizes what Director Tom Tyburski reported. In the same report, he said fundraising for Simsbury Celebrates was "going exceptionally well."
So, as of late October, the town had its sponsors and was short on gingerbread houses. The gingerbread houses are the part residents build themselves, and the entry deadline is Monday, November 16. That is twelve days before the festival fills Hopmeadow Street on Saturday, November 28.
That gap shapes Simsbury's whole season. Much of what people see in December is handmade by local residents: gingerbread in the library, hand-painted slates and sleds, and the craft tables at the Simsbury Historical Society's holiday market. Each of those pieces has its own date, and most of the dates come before the festival.
The Gingerbread Window Closes November 16
The Gingerbread House Exhibit has a reliable spot on festival night. The posted Simsbury Celebrates schedule puts it inside the Simsbury Free Library during the 5:00 to 7:15 PM block, and it notes that the exhibit closes promptly. The exhibit only fills if residents bring in entries. With about 9 entries against a usual 20 to 30 three weeks before the deadline, the library room could look noticeably thinner this year than in past years.
The Culture, Parks and Recreation department collects support for the festival through its Simsbury Celebrates page on the town recreation site, which lists a town email for questions. If you plan to enter a house, contact the department before Monday so your build goes into the exhibit and not your own kitchen window.
The sponsor side looks very different. The minutes name UConn Health as this year's presenting sponsor, with a booth at the event. BPS Lawyers joins as a new sponsor, and Vincent Funeral Home and the Goddard School have taken on large sponsorship roles. The Goddard School will also run the Santa photo line and put up an inflatable movie screen with holiday cartoons, so children waiting in line have something to watch.
November 21 Is the Workshop Before the Show
Five days after the gingerbread deadline, the Simsbury Historical Society holds the season's next hands-on event. Its Holiday Slate and Sled Painting runs Saturday, November 21, at the Ellsworth Visitor Center, with a morning session from 10 a.m. to noon and an afternoon session from 1 to 3 p.m.
The details:
- Slate painting: $20, on predrilled slates ready to hang
- Sled painting: $50
- Materials: supplied by the Historical Society, including design ideas for anyone who arrives without a plan
- Registration: required in advance, with payment, and space is limited
The workshop connects to festival night. During Simsbury Celebrates, the Historical Society's lawn shows 1850s painted sleighs, and its buildings host an 18th Century Workshop, the Phelps Tavern historic kitchen, and a Winter in a Wigwam tour. A sled painted on November 21 can be on someone's porch a week later, a short walk up Hopmeadow Street from sleighs painted about 170 years earlier.
Mornings at Simsbury Farms Run on a New Clock
The town's ice rink starts its season alongside the holiday calendar. At the same October meeting, Recreation Supervisor Jaimie Clout said Simsbury Farms Ice Rink was due to make ice the next day, under the tagline "Simsbury On Ice."
The minutes describe a reworked 2026-27 schedule meant to be more consistent:
| Session | When |
|---|---|
| Public skate | Every day, 10 a.m. to 12 p.m. |
| Skating lessons | Sunday afternoons, back to back |
| Sunday public skate | 2:15 to 4:15 p.m., right after lessons |
The rink is also running a BPS Free Skate this year, sponsored by the same firm that is new on the festival sponsor list. A "Skate Jam" event is under consideration. A daily late-morning session gives anyone with a free weekday morning a regular place to go well before the December rush.
Where It All Lands on November 28
Simsbury Celebrates follows a simple outline. Performances and activities run along Hopmeadow Street from 5:00 to 7:15 PM. The Simsbury Volunteer Fire Company's decorated firetruck parade follows at about 7:30 PM, and the fireworks launch from Simsbury Meadows Performing Arts Center at 8:15 PM.
Inside that outline, the posted schedule spreads events across a dozen buildings and lawns, and several offer timed sets you can plan around:
| Location | What's There | Times |
|---|---|---|
| First Church of Christ, Palmer Hall | HARTT Community Division, "The Nutcracker" | 5:15, 5:45, 6:15, 6:45 |
| First Church of Christ, Sanctuary | Farmington Valley Chorus of Sweet Adelines | 5:15 and 5:45 |
| Simsbury United Methodist Church | Messiah Community Sing Along with the Farmington Valley Chorale | 6:00 to 6:45 |
| Simsbury United Methodist Church | Carillon Concert | 7:00 to 7:30 |
| Eno Hall Auditorium | The Children's Museum Group, animal ambassadors and STEAM stations | 5:15 to 7:00 |
| Eno Hall, Old Court Room | Simsbury Garden Club holiday decoration displays and demonstrations | During the festival |
| Simsbury Public Library, Front Lawn | Selfies with Santa and Jingles the Elf | 5:00 to 7:15 |
| 1820 House Lawn | S'mores and fire pits with Scout Troop 76 and Liberty Bank | 5:00 to 7:15 |
| Fiddler's Green | Theatre Guild of Simsbury at the Coffee Spot; children's activities and book signings at The Lucky Gut Collective | During the festival |
A few smaller stops fill out the street. The Simsbury Camera Club shows photography in the Eno Hall Youth Room, and the Salvation Army Band plays on the front steps of Eno Hall. Northwest Community Bank sponsors an ice carving demonstration, and the Simsbury Lions Club runs family cornhole with cider and donuts at the library. Modern Vintage Opera and Danny Reilert's holiday music sets keep both the Historical Society's Meeting House and the library's Children's Room busy all evening.
Each of these ties back to the earlier deadlines. The gingerbread room at the Simsbury Free Library is the only stop on the list that depends on residents submitting entries in advance, and its line closes promptly. If you plan to see it, put it early in your route, before the 6:00 sing-along and well before the parade.
After the Fireworks, the Handmade Market Takes Over
Once the festival is over, the Ellsworth Visitor Center becomes the season's main stop. The Simsbury Historical Society runs its holiday events on a schedule that covers the first half of December:
- Wednesday, December 2, 6 to 8 p.m. The Holiday Sip & Shop opens the market with complimentary refreshments. No advance registration is needed.
- Thursday, December 3, through Sunday, December 6, noon to 4 p.m. Opening week of the Holiday Market, with Simsbury and "Simsbeary" gifts and apparel alongside jewelry, ornaments, handmade soaps, candles and artisanal food.
- Saturday, December 5, 2 p.m. A Victorian Holiday Tea Party in the 1771 Phelps Tavern, aimed at children ages 7 and up with an adult. Guests make a Victorian ornament and stay for holiday music. The fee is $40 per person, and registration is required.
- Thursday, December 10, through Sunday, December 13, noon to 4 p.m. The market's last week, with restocked inventory.
"Inventory is replenished so there's still time to find Simsbury and 'Simsbeary' gifts and apparel plus one-of-a-kind holiday gifts."
That line from the Historical Society's own listing explains why the market runs as two short weeks with a gap between them. The tea party is the only event in that stretch with a fixed seat count, and like the slate and sled sessions, it requires payment up front. In this part of the season, the events that need a sign-up are the ones with limited space, while the market's open hours have no limit.
All of this adds up to a calendar where most of the deciding happens in November. The gingerbread deadline is Monday the 16th. The painting sessions are Saturday the 21st. The festival is Saturday the 28th, and the tea party seats are already being filled for December 5. Everything after that is a matter of showing up between noon and 4 p.m.
At Jacek Mikolajczyk, our team works across the Farmington Valley every week, and Simsbury's December calendar is one we follow closely. Whether you are entering your first gingerbread house or looking for a parking spot near Hopmeadow Street on the 28th, we're glad to share what we know about the town. Our Simsbury neighborhood page is a good place to start. Let's Connect.
