Downtown San Leandro's December Runs Through Estudillo Avenue: Tree Lighting, Library Nights, and Where to Warm Up

At 5:30 p.m. on Friday, December 4, the lights go on at Estudillo Plaza, where Estudillo Avenue meets E. 14th Street. This is the tree lighting for the 29th annual It's a Wonderful Night. Up the same avenue at 300 Estudillo, the Main Library will host almost every other dated event this month: a singalong, a menorah lighting, a marionette show, a gingerbread morning, a screening of White Christmas and a balloon drop at noon on New Year's Eve.

Most of San Leandro's holiday dates for 2026 come from public institutions, mainly the City of San Leandro calendar, the San Leandro Public Library and the Downtown San Leandro district. Those institutions are clustered downtown, so the season is too. Thanks to a café that opened inside the library this year, you can now spend a December afternoon there without going back to the car.

The night that opens the season

It's a Wonderful Night is on Friday, December 4, from 5 to 9 p.m., and the City lists it as free. The Downtown San Leandro event page puts the main event on W. Juana Avenue in Butterfly Plaza. The tree lighting is at Estudillo Plaza.

Here's how the evening runs:

1. 5:00 p.m. The event opens on W. Juana Avenue.
2. 5:30 p.m. The tree lighting at Estudillo Plaza.
3. Through 9:00 p.m. Holiday performances, free photos with Santa, holiday train rides, a kids zone, a holiday market, holiday drinks and a toy drive.

If you're bringing something for the toy drive, have it in hand before you head out. The tree lighting is at Estudillo Avenue and E. 14th, on the same avenue as the Main Library, which is busy the very next afternoon.

The library takes it from there

On Saturday, December 5, from 3 to 4 p.m., the Main Library hosts A Seasonal Singalong. It's a free, family-friendly program with live music. After that, the library has something going on most weeks until the end of the year. Unless noted, everything below is at the Main Library, 300 Estudillo Ave.

Saturday, December 19 is the busiest day on the list. Families can go to the gingerbread playdate in the morning and stay for White Christmas at 2 p.m. That leaves a few hours in between, and since February those hours are easy to fill without leaving the building.

The café inside the library

Berkeleyside reported in February that As Kneaded Café planned to open at the Main Library on February 14. It's open now at 300 Estudillo Ave. and serves salads, sandwiches, pastries and espresso drinks. The coffee comes from Counter Culture, including the "Big Trouble" and "Hologram" blends.

The café changes how the month works. Without it, the gap between the gingerbread playdate and the movie meant driving off somewhere. Now there's lunch in the same building. The same goes for the Mug + Book Swap on December 15. It starts at 5:30 p.m., and the As Kneaded Café counter is right there.

Around the same time, Berkeleyside reported that Gold Bean Cafe had soft-opened at 138 Pelton Center Way. The outlet described it as a specialty-drinks café whose menu includes a churro latte and a Vietnamese-inspired egg coffee. Pelton Center is part of the same downtown, so Gold Bean is close by for a coffee before the singalong or the puppet show.

W. Juana Avenue after the tree lighting

The December 4 event takes over Butterfly Plaza on W. Juana Avenue, and two places with addresses on that block serve food and drinks.

Fieldwork Brewing, 100 W. Juana Ave. The taproom's location page lists daily hours, rotating beers, pizza, salads and small plates. Its menu is dated 11/8/2026. Fieldwork's San Leandro taproom is in the middle of the main event area.

Sons of Liberty Alehouse, 150 W. Juana Ave. The alehouse offers indoor seating, patio seating and takeout, with cocktails, wine, beer and comfort food. Sons of Liberty is a few doors down from Fieldwork.

Rocky's Charcoal Grill, 300 W. Estudillo Ave. Rocky's posts its hours and takes online orders for burgers, steak sandwiches, chicken and ribs. If you'd rather pick up dinner than wait for a table on a crowded night, Rocky's is the practical choice.

For more on how this stretch of downtown filled in over 2026, see our August post on what opened along E. 14th and why the corridor finally walks.

The rest of the city calendar stays close to E. 14th

The events outside the library follow the same pattern. They're run by the City or the police department, and most are on E. 14th Street.

• Holiday Cookies with the Cops. Thursday, December 10, 5:30 to 8:30 p.m., at the San Leandro Police Department, 901 E. 14th St. It's free and includes Santa, cookie decorating, crafts and games. The Bingo Bash at the library ends at 5 p.m. that day, so you can easily do both.
• Senior Community Center Holiday Event. Monday, December 21, 2 to 4 p.m., at 13909 E. 14th St. It's for ages 50 and up, with holiday trivia and seasonal treats.

Thanksgiving week comes first. On Wednesday, November 25, the Senior Community Center hosts a Thanksgiving Luncheon from noon to 2 p.m. with Spectrum Community Services. The same morning, from 8 a.m. to noon, City Recreation and Parks holds its annual Swim Now, Gobble Later lap swim at the Boys & Girls Club Pool, 2200 San Leandro Blvd. It costs $5 per person, and you need to register. All San Leandro public libraries are closed November 26 and 27 for Thanksgiving, so the library's holiday programs pick up again in December.

A note on San Leandro Boulevard

The swim is on a street with a major project on its schedule. Alameda CTC's project page for the East Bay Greenway set October 2026 as the construction start for the San Leandro Boulevard section and November 2027 as the expected finish, and the agency posts specific work locations about five days before crews arrive on a block. The work covers protected bike lanes, bus stop upgrades, repaving, new curbs and sidewalks, and landscaping. These are the points that matter for a December outing:

• Crews will work on no more than two blocks in a row, and the boulevard drops to one lane in each direction inside active work zones.
• Work hours are 7 a.m. to 7 p.m. on weekdays, with weekend work from 8 a.m. to 7 p.m. if needed.
• AC Transit Route 28 may have temporary stop closures and detours.
• Door hangers go up about five days before work starts on a block, and No Parking signs go up at least 72 hours ahead.

The Wednesday-morning swim falls inside weekday work hours. If you're driving to the pool, look for posted signs before you park. The project's outreach team can be reached at [email protected] or 1-888-642-4555.

Planning the month from one address

Put it all on one map and 300 Estudillo Ave. is the center. The library hosts seven of the December events in the table above, with the eighth at its Manor Branch. The library also has the café, and the tree lighting that opens the season is down the same avenue. A household could plan most of the season around that one building:

• Friday, Dec. 4: tree lighting at 5:30 p.m., then dinner on W. Juana.
• Saturday, Dec. 5: coffee at As Kneaded, then the singalong at 3 p.m.
• Thursday, Dec. 10: Bingo Bash at 4 p.m., then Cookies with the Cops at 5:30.
• Saturday, Dec. 19: gingerbread at 10:30 a.m., lunch at the café, White Christmas at 2 p.m.
• Thursday, Dec. 31: the balloon drop at noon.

Families who live in Estudillo Estates or close to downtown can walk to much of this. Everyone else can park once and stay put. Our San Leandro neighborhood page has more on the parts of the city around this stretch of E. 14th.

At Annie Tegner, we follow downtown San Leandro season by season, from the library calendar to new businesses opening along E. 14th. If you own a home near Estudillo Avenue and want to know what this year's changes mean for its value, get your free East Bay home valuation and we'll go over it with you.