Stafford WinterFest returns on Saturday, December 12, 2026, from 3:00 to 7:00 p.m. in downtown Stafford. If the weather is bad, it moves to Sunday, December 13. The official schedule lists a museum open house, a live nativity, wagon rides, a pop-up market, school performances, a bonfire, Santa, and hundreds of luminaries along Main Street.
Almost all of it is timed around one event: the Parade of Lights, which steps off at 5:00 p.m. The wagon rides pause while it runs. The band plays just before it starts, and the choir sings as it heads down Main Street. A road closure moves with the parade from 4:30 to 6:30 p.m. Once you plan around the parade, the rest of the evening is easy to fit in.
Saturday, Built Around 5:00 p.m.
Here is the Events & Celebrations Committee's schedule, set against the parade. The town notes that times may change.
| Time | What | Where | How it fits the parade |
|---|---|---|---|
| 2:00 p.m. | Main Street parking ban begins | Main Street | Clears the route three hours early |
| 3:00 to 7:00 p.m. | Museum open house | Stafford Historical Society, 5 Spring Street | Open the whole time |
| 3:00 p.m. | Live nativity with actors and animals | First United Methodist Church lawn, 8 Church Street | Starts two hours before step-off |
| 3:00 p.m. onward | Pop-up market of makers and community groups | Haymarket Common, 31 Main Street | Opens with the festival |
| 3:00 to 4:45 p.m. | Hyde Park wagon rides, first run | Meet near 5 Spring Street | Ends before the parade |
| About 4:45 p.m. | SHS Band and Color Guard | Haymarket Common | Just before step-off |
| 5:00 p.m. | Parade of Lights steps off | Olympic Annex and West Main Street | The main event |
| About 5:45 p.m. | Caroling with the SHS Choir | Haymarket Common | While the parade is on Main Street |
| 6:00 to 7:00 p.m. | Hyde Park wagon rides, second run | Meet near 5 Spring Street | Starts once the parade has passed |
The wagon rides make the pattern easy to see. They are first come, first served, they run in two blocks with a gap from 4:45 to 6:00, and the schedule says they "may vary based on road closure schedule." If a wagon ride is on your list, aim for the first block. After the parade, the second block falls in the last hour of the festival.
The Route, From Olympic Annex to Holt Fountain
The parade starts at the corner of Olympic Annex and West Main Street, also Route 190. It turns onto Main Street and ends at Town Hall and Holt Fountain. The town keeps the viewing advice short:
"Viewing is everywhere between Olympic Circle and Town Hall."
That line comes from the WinterFest page on Explore Stafford. The parade starts just after dusk, and every entry is asked to be brightly lit.
Holt Fountain at the end of the route is older than any of these traditions. A 2022 town planning draft says the Holt Memorial Fountain was built in 1894 from Monson, Massachusetts stone as a drinking spot for people and animals. Joanna Holt and Celia Holt donated it in memory of the manufacturer Charles Holt, Joanna's husband and Celia's father. The parade ends there, at the same fountain, more than 130 years later.
Haymarket Common at 31 Main Street hosts the market, the band, and the choir, so it fills up at 4:45 and again at 5:45. The site used to be a gravel lot. The town took it on as an ARPA-funded improvement project, with plans calling for pavers, seating, lawn, lighting, plantings, and space for public events and the arts.
Parking Is Decided at 2:00 p.m.
According to the Events & Celebrations Committee, the Main Street parking ban starts at 2:00 p.m., an hour before the festival opens. The road closure starts at 4:30 and moves with the parade from Olympic Circle to Holt Fountain until about 6:30. If you plan to drive, park off Main Street before 2:00.
For its downtown evenings, the town lists these free parking spots:
- The Spring Street public lot next to Eagle Mart
- Stafford Town Hall, 1 Main Street
- Side streets, unless posted otherwise
The Spring Street lot is closest to the wagon rides, which leave from near the Historical Society at 5 Spring Street.
The Parade Has a Contest This Year
This year the Events & Celebrations Committee is adding a float and entry contest, with entries decorated in festive holiday themes competing for recognition in several categories. Entering the parade is free. Businesses, clubs, civic groups, and individual residents can all enter a float, a marching group, or a decorated vehicle.
Entries line up on the west side of downtown, and the instructions are specific:
- Lineup begins at 4:00 p.m. on Olympic Avenue, and step-off is "5:00 PM sharp."
- All parade vehicles enter through Summer Street from Monson Road, also Route 32, across from Sara Mart/Getty. Olympic Avenue is one-way during staging, and entry from Olympic Circle is not allowed.
- Check in at the corner of Summer Street and the Olympic Field parking lot to get your lineup spot. Entries are placed in order of arrival, grouped by type.
- The Olympic Field lot has limited parking for non-parade vehicles, and cars parked there cannot leave until the parade has left Olympic Avenue. The American Legion at 10 Monson Road is letting non-parade vehicles use its lot, but you will have to cross Route 32 on foot.
- To drop off walkers, enter Olympic Circle from Route 190 and leave by Olympic Annex. Drop-off vehicles are not allowed in the staging area.
Registration and the full rules are on the parade registration page. With a contest added, expect more effort on the lights. Lighted decorations, string lights, and battery-operated lights are all encouraged.
Friday Night Comes First
The night before WinterFest is the second Friday of December, which means Arts on Main. The town lists the December session for Friday, December 11, at 6:00 p.m. The monthly event runs 6:00 to 8:00 p.m. at participating businesses along Main Street.
The town's description of Arts on Main lists local artists and makers, live demonstrations, DIY art projects for all ages, special sales at participating businesses, pop-up performances, and live music. The Main Street Businesses put on the Main Street Music Series, and its concerts have been held at Haymarket Common. The Arts on Main Stafford page on Facebook posts each month's participating businesses and featured artists.
Friday has no parking ban and no road closure. Both nights use the same stretch of Main Street, but only Saturday is organized around a moving closure.
Eating Around the Closure
Saturday's food plans depend on which places are open when.
LuAnn's Bakery & Cafe, 42 Main Street, is open Monday through Saturday from 6:30 a.m. to 2:00 p.m. On WinterFest Saturday, it closes as the parking ban starts, so it works for breakfast or lunch before the festival but not for parade night. Its holiday specials at the Stafford cafe began November 2. The 2026 Thanksgiving menu takes orders through Thursday, November 19.
Stafford House of Pizza, 19 Main Street, lists Friday and Saturday hours running until 10:30 p.m. or later for the week of November 9 on its ordering page. Check the page that week for the December 12 hours.
Crazy Cock Cider, the Stafford Cidery taproom at 68 Main Street, lists Saturday hours of 1:00 to 9:00 p.m. on its own site. It also pours Connecticut-brewed beer and wine. It does not serve food, but guests can bring their own. Pizza from 19 Main Street is close by.
Two Stops That Don't Depend on the Parade
The Stafford Historical Society museum at 5 Spring Street is open the full 3:00 to 7:00 p.m., with two floors of local history and a small gift shop. The building itself is part of the history. It went up between 1887 and 1889 as Julius Converse's office and mineral-water bottling plant. It became the town library after Julia Johnson bought it in 1896, and it became the Society's museum after the library moved in 2001. The collection includes photographs of the springs, hotel advertisements, and mineral-water bottles and labels. Wagon riders meet near the museum, so you can tour it while waiting for the 6:00 run.
The other is the big red Letters to Santa mailbox outside the Police Station. Each letter needs the sender's first and last name and a return mailing address so a reply can be sent. You can drop letters off at any point in the evening.
Keep Sunday, December 13, open in case the weather moves everything back a day.
If your WinterFest weekend also has you thinking about a move in the year ahead, the Moriarty Team would be glad to talk it through quietly, on your timeline. Pam Moriarty Real Estate works with Stafford homeowners and buyers across Tolland County. Schedule a free consultation.
