On the evening of November 28, a set of 1850s painted sleighs will sit on the Simsbury Historical Society lawn. Down Hopmeadow Street, gingerbread houses built to the theme "Historical Significance" will fill Simsbury Free Library until the exhibit closes promptly at 7:15 p.m. The gingerbread theme marks America's 250th anniversary. It also describes the rest of Simsbury's 2026 holiday calendar. Simsbury Celebrates is the town's big night, but it is one evening. Across November and December, the Historical Society campus at 800 Hopmeadow Street and 10 Phelps Lane carries twelve days of programming.
So the season runs on the Historical Society's calendar more than the town's. The season starts with a deadline that comes before any of the events, and a full calendar in date order closes the post.
The Gingerbread Deadline Comes First
The town's gingerbread competition is part of Simsbury Celebrates, and everything else in it depends on its registration deadline. Registration closes Tuesday, November 17, 2026. The first 30 entries are guaranteed a spot, and late entries get in only if space allows. Finished houses go to Simsbury Free Library, 749 Hopmeadow Street, on Sunday, November 22, between 1:00 and 3:00 p.m., and stay on display for a week.
There are two changes this year. The "Historical Significance" theme ties into America's 250th, though following it is encouraged rather than required. A new People's Choice Award will be decided by votes at the Gingerbread House Cocktail Party. Registration is on the Town of Simsbury recreation page for the competition.
Drop-off on November 22 starts the one-week display, so the houses are up during Thanksgiving week and come down shortly after Simsbury Celebrates. If a family member is building one, November 17 matters more than November 28.
November 21 Comes a Week Before Celebrates
The Saturday before Thanksgiving is the Historical Society's busiest November day, and two of its programs connect directly to what happens on Hopmeadow a week later.
- Blacksmithing Class, 9 a.m. to noon. Participants work at the forge in the Griswold-Ensign Blacksmith Shop under blacksmith Paul Spirito. The fee is $95 per person per class, participants must be 18 or older, classes are small, and pre-registration is required. The same class runs again on December 19.
- Slate and Sled Painting, 10 a.m. to noon or 1 to 3 p.m. This one is at the Ellsworth Visitor Center. All materials are included, and advance registration and payment are required.
The sled painting takes place a week before 1850s painted sleighs go on display on the same society's lawn for Simsbury Celebrates. Whoever paints a sled on November 21 can see the 19th-century version on November 28.
The week before, on Sunday, the Simsbury Public Library's Comfort & Joy Holiday Card Drive runs all day on November 15.
Simsbury Celebrates, Saturday, November 28
The date appears on the Simsbury Celebrates event schedule and in the October 22, 2026 Culture, Parks and Recreation Commission agenda. Performances and activities run along Hopmeadow Street from 5:00 to 7:15 p.m. The Simsbury Volunteer Fire Company's decorated firetruck parade follows at about 7:30 p.m., and fireworks launch at 8:15 p.m. from Simsbury Meadows Performing Arts Center.
The evening has more performances than anyone can see in two hours and fifteen minutes. The table below shows the schedule as currently posted, grouped by building so a route can be planned from one end of the street to the other.
| Venue | What's scheduled | Times as posted |
|---|---|---|
| Simsbury Free Library | Gingerbread House Exhibit; Farmington Valley Chorus of Sweet Adelines | Exhibit closes promptly at 7:15 p.m. |
| Simsbury Historical Society | 1850s Painted Sleighs on the lawn; 18th Century Workshop and Phelps Tavern Historic Kitchen; Winter in a Wigwam Tour | 5:00 to 7:15 p.m. window |
| Historical Society Meeting House | Modern Vintage Opera | 5:20, 5:55, 6:30, 7:00 p.m. |
| First Church of Christ, Palmer Hall | HARTT Community Division, "The Nutcracker" | 5:15, 5:45, 6:15, 6:45 p.m., 15 minutes each |
| First Church of Christ | Live Nativity | 5:00 to 7:15 p.m. window |
| Simsbury United Methodist Church | Messiah Community Sing Along with the Farmington Valley Chorale; Carillon Concert | 6:00 to 6:45 p.m.; 7:00 to 7:30 p.m. |
| Simsbury Public Library | Selfies with Santa and Jingles the Elf on the lawn; Danny Reilert in the Children's Room; Falcetti School of Music, then Playhouse on Park, in the FSPL Room; Mandell JCC and FVJC in the Tariffville Room | Reilert 5:15, 6:00, 6:45 p.m.; Falcetti 5:00 to 6:05 p.m.; Playhouse on Park 6:10 to 7:15 p.m. |
| Scout Hall | Kinetic Ukes | 5:15, 6:00, 6:45 p.m. |
| 1820 House Lawn | S'mores and fire pits with Scout Troop 76 and Liberty Bank | 5:00 to 7:15 p.m. window |
| CVS parking lot | Play Strong Block Party | 5:00 to 7:15 p.m. window |
| Coffee Spot | Theater Guild of Simsbury | 5:00 to 7:15 p.m. window |
The schedule also lists ice sculpting sponsored by Northwest Community Bank, a strolling holiday cabaret from SHS, and a Valley Simsbury Church adventure tent with a food bank collection on the Bank of America lawn. Eno Hall has its own lineup: animal demonstrations, STEAM stations, Simsbury Garden Club displays, a Salvation Army Band performance, and a booth for recording holiday greetings for Simsbury Community TV. The Simsbury Camera Club gallery is in the Eno Youth Room.
One Way Through the Evening
Most of the performances that repeat do so every 30 to 45 minutes, so the order of stops matters less than knowing which ones only happen once. Here is one sequence that works with the posted times:
- 5:00 p.m., Simsbury Free Library. Start with the gingerbread houses, since the exhibit is open only during the activity window and closes promptly at 7:15.
- 5:15 p.m., Palmer Hall. Catch the first 15-minute "Nutcracker" slot from the HARTT Community Division.
- 5:30 p.m., Historical Society. See the painted sleighs, the Phelps Tavern Historic Kitchen and the Winter in a Wigwam Tour, then the 5:55 to 6:15 Modern Vintage Opera set in the Meeting House.
- 6:15 p.m., Simsbury United Methodist Church. Join the Messiah sing-along, which runs once, from 6:00 to 6:45, for its second half.
- 7:00 p.m. Stay at the church for the Carillon Concert, which runs until 7:30, or head to the 1820 House lawn for s'mores before the parade.
- About 7:30 p.m. Watch the firetruck parade, then the 8:15 fireworks over Simsbury Meadows Performing Arts Center.
The Messiah sing-along and the Carillon Concert are the only performances on that route that happen once.
December Moves to the Ellsworth Visitor Center
Once the fireworks are over, the town has nothing else on its holiday calendar for the season, and the Historical Society takes over. Its Holiday Market opens with a Holiday Sip & Shop on Wednesday, December 2, from 6 to 8 p.m. at the Ellsworth Visitor Center, 10 Phelps Lane. There are complimentary refreshments and no advance registration. After that, the market keeps daytime hours:
- Holiday Market, Week 1: Thursday through Sunday, December 3 to 6, noon to 4 p.m.
- Holiday Market, Week 2: Thursday through Sunday, December 10 to 13, noon to 4 p.m.
The society lists Simsbury and "Simsbeary" gifts and apparel along with jewelry, ornaments, handmade soaps, candles and artisanal food. Neither week requires registration. The market runs Thursday through Sunday afternoons, so the December 2 Sip & Shop is its only evening.
In the middle of Week 1, on Saturday, December 5, at 2 p.m., the society hosts a Victorian-style Children's Holiday Tea Party in the decorated Phelps Tavern at 800 Hopmeadow Street. It is for children 7 and older accompanied by an adult. The tavern is not wheelchair accessible. On December 5, one trip to the campus can cover both the tea party and the market a few steps away.
The final blacksmithing class is Saturday, December 19, 9 a.m. to noon, six days after the market closes.
The Season by Date
Counting each day separately, the Historical Society holds twelve days between November 21 and December 19: the Saturday programs, its part in Simsbury Celebrates, the Sip & Shop, eight market days, and the closing forge class. The town's Simsbury Celebrates is one evening, preceded by a registration deadline and a drop-off.
- Nov. 15: Comfort & Joy Holiday Card Drive, Simsbury Public Library
- Nov. 17: Gingerbread registration deadline
- Nov. 21: Blacksmithing and Slate and Sled Painting, Historical Society
- Nov. 22: Gingerbread drop-off, Simsbury Free Library, 1 to 3 p.m.
- Nov. 28: Simsbury Celebrates, 5 p.m. through 8:15 p.m. fireworks
- Dec. 2: Holiday Sip & Shop, Ellsworth Visitor Center, 6 to 8 p.m.
- Dec. 3 to 6: Holiday Market, Week 1, noon to 4 p.m.
- Dec. 5: Children's Holiday Tea Party, Phelps Tavern, 2 p.m.
- Dec. 10 to 13: Holiday Market, Week 2, noon to 4 p.m.
- Dec. 19: Final blacksmithing class, 9 a.m. to noon
Questions about any Historical Society event can go to [email protected], mentioning the event by name. The society's events page has registration links for the forge and painting sessions.
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