Alameda's Holiday Season Saves Its Biggest Night for One December Saturday

On Saturday, December 5, Alameda has four separate holiday traditions in the same few hours. The Downtown Alameda Winter Market runs from 1 to 7 p.m. The City's Winter Lights Celebration takes place in front of City Hall from 4 to 6 p.m., and the tree lighting starts at 5:30. The Lighted Yacht Parade starts down the Alameda side of the estuary at about 5:30, the same moment. The Hot Cocoa Stroll starts as daylight fades. The next morning, the Alameda Point Antiques Faire opens for its December date.

Most of the season's big public events fall on that one weekend. The rest of the calendar, from this weekend's Haunted House to Breakfast with Santa a week after the tree lighting, is spread out. The weekends between are when you can take each event at an easy pace and save your energy for the 5th.

December 5, Hour by Hour

Here's the evening laid out in order, using times the organizers have posted.

The table makes the one real conflict easy to see. The tree lighting and the yacht parade both happen around 5:30, so you have to pick one.

Planning Around the 5:30 Conflict

Everything else that day fits together. The Downtown Alameda events page describes the Winter Market and the Hot Cocoa Stroll as one continuous evening: "As daytime turns to dusk, the lights start to twinkle and the Hot Cocoa Stroll will begin." Participating businesses will offer "a delectable assortment of sips & nibbles," and the stroll is free.

Here are the two versions of the evening I'd suggest:

1. The downtown version. Get to the Winter Market in the afternoon while there's still daylight, then head to City Hall before 5:30 for the tree lighting. The City's Fall 2026 activity guide lists music, Dancing Christmas Trees and photos with Santa during the 4-to-6 window, with more entertainment to be announced at alamedaca.gov/winterlights. After the tree lights up, go back for the Cocoa Stroll. The market stays open until 7.
2. The waterfront version. Do the Winter Market early, then head for the estuary. According to the parade organizer's route, boats line up between Wind River and the Fortman Marina public pier. Around 5:30 they head down the Alameda side, past the judges at the Encinal and Oakland Yacht Clubs and then past Pasta Pelican. At Jack London Square they cross to the Oakland side, run back along it and finish at the staging area by Fortman Marina. The route page doesn't say where the public can watch. The yacht clubs are listed as places the boats pass, not as public viewing spots, so check before you assume you can walk in.

The route loops back to where it started, so the boats are on the water for a while after 5:30. The tree lighting is a single moment at City Hall. If your group can't agree, that difference may decide it.

The Weekends Before Are the Easy Ones

The season starts well before December, and the first events are spread out.

This weekend, October 23 to 25, Alameda Recreation & Parks puts on its Haunted House at South Shore Shopping Center, between Daiso and TJ Maxx. Hours are 2 to 9 p.m. Friday and Saturday and 2 to 7 p.m. Sunday. Teen volunteers build it for visitors of all ages, and you'll need cash or a physical card to buy tickets at the door, so a phone wallet won't work.

Thursday @ the Avenue has two weeks left, tonight, October 22, and October 29. It runs from 5 to 7:30 p.m. on Alameda Avenue with live family-friendly music, outdoor games from All Good Living, and vendor pop-ups.

Halloween is on a Saturday this year, and the West Alameda Business Association has planned Howl-O-Ween on Webster for the whole day. Participating Webster Street businesses will hand out treats to trick-or-treaters during the day. The pet costume contest runs from 2 to 4 p.m. at Webster Park, 1435 Webster Street. "Last year showed us just how much people love seeing Webster Street filled with costumes, pets, families, and neighbors," WABA Executive Director Elissa Glickman told the Alameda Post. Entering the contest is free, but only the first 30 registered pets get on stage, so if your dog already has a costume, register early on WABA's Howl-O-Ween page.

November Is for Gift Shopping

The day after Halloween, the season turns to shopping, and November's events each get their own weekend.

• Sunday, November 1: Alameda Point Antiques Faire. The official ticket listing describes more than 800 dealer booths, items at least 20 years old, and free parking. The Faire's homepage lists November admission times from 6 a.m. through 3 p.m.
• November 1 through December 15: Alameda All Wrapped Up. The City runs this shop-local campaign with the Downtown Alameda Business Association and WABA. Each day features a different theme, such as Dining Around Alameda, Vintage & Handmade Art, Gifts & Home, and Kids & Family. You collect a ticket with each purchase or ask for one, then enter the ticket numbers online for that day's drawing. There are 12 themed prize collections. Winners are announced December 18. Details are on the City's All Wrapped Up page.
• November 7 and 8: the 46th annual Alameda Holiday Boutique. Local artisans sell handmade gifts, along with food and other activities, from 10 a.m. to 4 p.m. both days at 641 West Redline Avenue, according to the City's events page. The City's activity guide gives that address as the Albert H. DeWitt O'Club.
• Saturday, November 28: Small Business Saturday. Downtown Alameda lists the Saturday after Thanksgiving as its day to shop and dine locally.

All Wrapped Up runs the whole time, so every November purchase at a participating business can also count as a drawing entry. A Holiday Boutique gift or a Small Business Saturday dinner can earn a ticket, as long as you remember to ask for one.

After the Big Weekend

The second half of that weekend comes the next morning. The Antiques Faire's December date is Sunday, December 6. The Faire's homepage lists November hours, so confirm December hours closer to the date.

On Saturday, December 12, Breakfast with Santa returns to the O'Club at 641 West Redline Avenue from 10 a.m. to noon. Everyone needs to register in advance, whatever their age, and registration closes December 4, the day before the busy Saturday. Prices are $35 for residents and $40 for nonresidents age 13 and up, and $15 and $20 for ages 2 to 12. Children under 2 are free. Space is limited, and the City's guide says no refunds or credits will be issued. If you plan to go, put the registration deadline on your calendar now.

Christmas Tree Lane on the 3200 block of Thompson Avenue doesn't follow a city schedule. Its 2026 dates and hours hadn't been posted as of mid-October. The tradition began in 1938 and has paused only a few times, during World War II. In a 2022 Alameda Post guide written with residents of the lane, the lights generally came on the first weekend of December and stayed on nightly from 5 to 10 p.m. through the month. That's a past pattern, not a 2026 announcement. If it holds this year, the lane would light up the same weekend as the tree lighting and the yacht parade. The same guide suggested parking a block away and walking. For drivers, it said Fernside Boulevard has less traffic coming in, and it asked everyone to drive slowly.

The All Wrapped Up drawings end December 15, and the City announces winners December 18.

A lot of the homes on Thompson Avenue and around downtown are older Alameda houses that people have cared for over many years, and I enjoy seeing them lit up. If a walk through the neighborhood this season gets you thinking about your own house, whether that's an update, a repair you've been putting off, or what comes next for a family home, I'm glad to talk it through at no cost. Joe LoParo is here when you're ready. Let's Connect.