Cityline Winter Ice opens at Redwood Square, 273 S. Murphy St., on Tuesday, November 24, and runs through January 3, 2027. The night that matters most this season comes one day after opening. Starting Wednesday, November 25, every Wednesday has its own theme and a local radio host, with sessions at 7:30 and 9 p.m.
That Wednesday schedule shapes the whole season. Weekday public hours don't start until mid-afternoon, and private buyouts take some early-December evenings, so the Wednesday night sessions are the most predictable public time on the ice.
Six Wednesdays, two sessions each
Cityline's rink page lists the season's "Midweek Magic on Ice" nights, put on with iHeart Radio's local stations:
| Wednesday | Theme | Hosted by | What to bring |
|---|---|---|---|
| Nov 25 | Glow Night | STAR 101.3 | Nothing extra. A free glow-in-the-dark surprise is handed out while supplies last |
| Dec 2 | K-Pop Night | Wild 94.9 | Your favorite group's colors or merch |
| Dec 9 | Taylor's Birthday | STAR 101.3 | An outfit from your favorite era |
| Dec 16 | Millennial Magic | Wild 94.9 | Early-2000s nostalgia |
| Dec 23 | Ugly Sweater Night | Wild 94.9 | The loudest holiday sweater you own |
| Dec 30 | 80s Night | Greatest Hits 103.7 | Neon, leg warmers, retro gear |
All six nights have the same two start times, 7:30 and 9 p.m. Glow Night falls the night before Thanksgiving and 80s Night the night before New Year's Eve. The four Wednesdays in between land squarely in December.
Why early December runs on Wednesday nights
From November 30 to January 3, public skating on weekdays starts at 3 p.m. and runs until 10 p.m. Weekends run from noon to 10 p.m. Every session is 60 minutes.
Private parties take some of those weekday hours. From November 30 to December 16, the rink rents out exclusive sessions on select Mondays, Tuesdays and Wednesdays from 4 to 7 p.m. They cost $5,000 for up to 200 guests, and public skating is closed while a private group has the ice. Cityline pitches these sessions for holiday celebrations and corporate gatherings, and the 4 to 7 p.m. window covers most of the weekday afternoon public hours.
The private window ends at 7 p.m. The first themed session starts at 7:30. So on December 2, 9 and 16, even a Wednesday with a private booking in the late afternoon still has both public theme sessions later that night. If you're aiming for a weekday skate in the first half of December, the Wednesday evening sessions are the ones that sit outside the buyout hours.
When the schedule opens up
Two stretches of the season run on longer holiday hours, with the ice open from noon to 10 p.m. every day:
- November 25 to 29, which covers Thanksgiving week from Glow Night through the Sunday after
- December 19 to January 3, which covers the last two weeks of the season, including Ugly Sweater Night and 80s Night
Between those two stretches, weekday public skating doesn't start until 3 p.m. From December 19 on, the rink opens at noon every day until the season ends.
What $25 covers, and what costs extra
General admission is $25, and skate rental is included. The extras:
- Locker: $5
- Skate helper: $6. These are for beginners who need support, and there are only a few, given out first come, first served
- Socks: $5
If you're bringing a first-time skater, arrive early to get a skate helper. The skate change area holds up to 125 people, and the restrooms are portable units on site. Skates aren't allowed inside the restrooms. Cityline suggests comfortable layers, a jacket and gloves, because the ice can feel chilly.
Parking is free in Cityline's nearby garages and lots, and the rink is within walking distance of the Sunnyvale Caltrain station. That works well for a Wednesday after work. You can skip the drive home, take the train in, skate the 7:30 session, and catch a train back.
This season the rink is also partnering with Second Harvest of Silicon Valley on Skate for Meals. The goal is to raise $26,000, enough for 52,000 meals for people facing food insecurity in Santa Clara and San Mateo counties. Donations go through Second Harvest's campaign page.
The block around the rink has grown since the rink started
The rink debuted in 2019, took 2020 off and came back for a season that ran from November 19, 2021, to January 2, 2022, as the Sunnyvale Voice reported at the time. In 2026, there's a lot more to do before and after a session within a short walk of Redwood Square.
Coffee and tea before a 3 p.m. skate. Home Coffee Roasters opened at 200 W. McKinley Ave., Suite 100, on June 27, 2025, according to Palo Alto Online. Check Cityline's store page for its current hours before you go. In the same building at Suite 105, teazzi Tea Shop lists its hours and takes online orders, so you can pick up a drink on the way to the rink.
A burger between the 7:30 and 9 p.m. sessions. Shake Shack's address is 275 S. Murphy Ave., two street numbers from the rink's 273 S. Murphy St. address. The Mercury News reported in March that it was set to open on April 1, 2026. It now appears in Cityline's directory.
A sit-down dinner. The same directory lists Senro Sushi, Pacific Catch, Urban Plates and the Melt. City permit records put Senro at 240 S. Taaffe St., Suite J134. If you'd rather cook, Whole Foods and Target are in the same development.
Names still marked "Coming Soon." Cityline's directory shows Haldiram's, Joe & the Juice and Sana'a Coffee House with that label. Check the directory before you plan around any of them.
The rink page itself points skaters toward Historic Murphy Avenue for food after a session. Murphy Avenue starts a block away.
The first weekend in December, off the ice
The first weekend after the Dec. 2 K-Pop Night packs three local events into about 18 hours.
- Friday, December 4, 4 to 5 p.m. The Sunnyvale Main Library at 665 W. Olive Ave. hosts a free Holiday Postcards program. You don't need to register, but space is limited.
- Saturday, December 5, 8:30 to 11 a.m. The City's Breakfast with Santa is at the Sunnyvale Senior Center, 550 E. Remington Drive. Tickets went on sale October 7.
- Saturday, December 5, 9 a.m. to 1 p.m. The Sunnyvale Farmers' Market sets up at Murphy Avenue and Washington. It runs every Saturday, year-round, rain or shine.
Saturday's weekend rink hours start at noon. That means December 5 can run from breakfast on Remington, to the market on Murphy before it closes at 1 p.m., to the ice at Redwood Square once it opens at noon. The City lists Winter Ice and Breakfast with Santa together on its special events page as part of its winter holiday schedule.
Tickets for every session, including the six Wednesday theme nights, are sold through the "Buy Tickets" link on Cityline's rink page. For ticketing questions, call (408) 676-7877.
See you on the ice! If you're skating K-Pop Night or showing up to Ugly Sweater Night in full pom-pom glory, tag me so I can share it. Downtown Sunnyvale is part of my everyday, and I love seeing my neighbors out there. If all this holiday energy has you curious about what your own place downtown is worth these days, Homes by Brianna can put together a free home valuation for you, no pressure and no ice skates required.
