On the Saturday before Thanksgiving, the giant balloons get inflated on Hoyt Street at Summer Street. Fifteen days later, Santa comes down the side of Landmark Square, 22 stories up. Over those two weeks, Stamford's holiday calendar leaves downtown, goes to the harbor, heads up to the north end of the city and then returns to Bedford Street to finish.
Harbor Point holds its own tree lighting on a Wednesday, and downtown holds another the next Sunday. On the same Wednesday evening as the harbor lighting, a holiday market runs at the Stamford Museum & Nature Center on Scofieldtown Road. If you plan the season around neighborhoods instead of one headline date, it gets a lot easier to fit in.
Downtown Opens It on Hoyt and Summer
The Stamford Downtown Parade Spectacular is Sunday, November 22, from noon to 2 p.m. Stamford Downtown calls it the official kick-off to the holiday season and describes it as one of the largest parades of its kind in the country, with giant helium balloons, marching bands and dance groups.
The day before has its own program. The Point72 Giant Balloon Inflation Party runs Saturday, November 21, from 3 to 6 p.m. on Hoyt Street at Summer Street. It has live music, performances and an appearance by Santa, and you can watch the balloons fill up close.
That Saturday is the busiest day of the season, and most of it happens downtown:
- 11 a.m. to 12:30 p.m. The Ferguson Library's Bake & Decorate Cookies session for grades 3 through 5 meets in the Main Library CreateLab. Registration is required.
- 10 a.m. to 4 p.m. The Friends Book Shop's fall and winter Bag Sale runs in the Harry Bennett Branch auditorium.
- 3 to 6 p.m. The balloon inflation party on Hoyt at Summer.
- 8 p.m. Tommy James and The Shondells play the Palace Theatre.
The Palace has a show the night before too. Electric Avenue plays Friday, November 20, at 8 p.m.
Last year's route gives a rough idea of where people stand. The 2025 parade started near Summer and Hoyt, went south on Summer, turned east on Broad and then went south on Atlantic, according to Hey Stamford's 2025 parade guide. Its stage and viewing spots were near North Street, on Summer past Spring, at Broad and Atlantic, and at Atlantic and Main. The same guide listed the Bedford Street, Summer Place, Stamford Town Center and Landmark Square garages as free on Sunday. Stamford Patch reported that downtown road closures for the 2025 parade started between 7 and 8 a.m., with streets expected to reopen by 4 p.m.
The Run, Mapped by Part of the City
| Date | Event | Where in Stamford |
|---|---|---|
| Sat, Nov. 21, 3–6 p.m. | Point72 Giant Balloon Inflation Party | Downtown, Hoyt St. at Summer St. |
| Sun, Nov. 22, noon–2 p.m. | Stamford Downtown Parade Spectacular | Downtown |
| Thu, Nov. 26, 8–9:30 a.m. | 15th Annual Harbor Point Turkey Trot 5K Fun Run | Harbor Point |
| Fri, Nov. 27, 2–3 p.m. | 8-Legged Art Drop-in | Stamford Museum & Nature Center, Bendel Mansion |
| Wed, Dec. 2, 4–8 p.m. | Holiday Artisan Market | Stamford Museum & Nature Center, 151 Scofieldtown Rd. |
| Wed, Dec. 2, 5:30–6:30 p.m. | 16th Annual Harbor Point Christmas Tree Lighting | Harbor Point Square |
| Sun, Dec. 6 | Heights & Lights and the Holiday Tree lighting | Downtown, Landmark Square to Latham Park |
Thanksgiving Morning Moves to the Water
Four days after the parade, the season moves to the harbor. The 15th Annual Harbor Point Turkey Trot 5K Fun Run is Thursday, November 26, from 8 to 9:30 a.m. The Harbor Point events calendar invites runners and walkers alike.
The Stamford Museum & Nature Center is closed on Thanksgiving Day. It reopens Friday, November 27, with a free 8-Legged Art Drop-in from 2 to 3 p.m. in Bendel Mansion. That gives families a free afternoon in north Stamford on the day after Thanksgiving, while downtown is still cleaning up from the parade weekend.
The Palace fills the rest of that week. STOMP plays Wednesday, November 25, at 7 p.m., and Jessica Lynn plays Sunday, November 29, at 7 p.m.
Late November is also when Mill River Park says the Cohen Skating Center reopens for its 2026–27 season. The park's rink page has the latest on opening day.
December 2 Puts Two Events Across Town From Each Other
On Wednesday, December 2, the city has two evening events happening at once.
At Harbor Point, the 16th Annual Christmas Tree Lighting runs from 5:30 to 6:30 p.m. in Harbor Point Square. The calendar places it near the square's restaurants, Bareburger among them. This is the square's first holiday season since Fortina at 120 Washington Boulevard closed. Its last day was August 31, after more than 10 years, as Stamford Patch reported.
Up on Scofieldtown Road, the Stamford Museum & Nature Center's free Holiday Artisan Market runs from 4 to 8 p.m. in the Astronomy Center & Planetarium at 151 Scofieldtown Road, with more than 30 vendors.
The market starts an hour and a half before the tree lighting and runs an hour and a half after it ends. You can shop early and drive south for the lighting, or catch the lighting and drive north to shop before 8.
Downtown Finishes It at Latham Park
The season comes back downtown on Sunday, December 6, for Heights & Lights. Stamford Downtown says Santa Claus, Rudolph, the Grinch and friends will rappel 22 stories down Landmark Square, followed by a fireworks show. Then Santa and company march up Bedford Street to Latham Park for holiday music and the lighting of Stamford's Holiday Tree. Stamford Downtown suggests parking at Stamford Town Center, the Bell Street Garage or the Summer Street Garage.
That makes the second tree lighting in four days, in a second part of the city. The Harbor Point lighting takes an hour on a weeknight in the square by the water. The Latham Park lighting comes at the end of a rappel, fireworks and a parade up Bedford Street.
The Palace has one show at each end of that week. Songs of The Season plays Friday, December 4, at 7 p.m. Be Like Blippi! plays Sunday, December 6, at 2 p.m., the same day as Heights & Lights, so families with small children can make both.
Mill River Park's two-day Holiday Market comes the following weekend. It runs December 12 and 13, from 11 a.m. to 5 p.m., at the Whittingham Discovery Center, 17 W Park Place.
Quieter Dates Before the Parade
The Ferguson Library has two early events on the holiday theme. Thursday, November 12, is the date of the library's all-day Winter Tales Short Story Contest. It's virtual, open to all ages, and asks for original stories inspired by winter or the holidays. On Saturday, November 14, "Latin & Ballroom Dance Classes: Groove into the Holidays" runs from noon to 1 p.m. in the Main Library's Dudley N. Williams, Jr. Auditorium.
Eating Downtown on Parade Weekend
Two restaurant changes affect where you might eat on a parade or Heights & Lights day. The Stamford Advocate reported in September that Quartiere at 51 Bank Street had closed after five years. The same report said Peruvian restaurant Fiesta on Main was moving into that space from 249 Main Street.
On the west side of the city, 7th Street Burger lists a Stamford location at 2000 West Main Street. CT Bites reported in August that the location was planned to open in November 2026.
Over the years, the Marion Filley Team has learned that where a home sits in Stamford makes a difference: near the harbor, on the north end or a few blocks from Bedford Street. If this season has you thinking about what your place in the city is worth, request a home valuation and we'll go through it with you.
