Where will you be at 5:30 p.m. on Saturday, December 5? Five events share the date this year, from a flea market at Alameda Point to a lighted boat parade on the Estuary. Three of them start within half an hour of each other.
From morning through midafternoon there's room to spare. A flea market opens at 10, a street market at 1, and you can walk between Park Street blocks at an easy pace. Then the sun drops. In about thirty minutes the City lights its tree on Santa Clara Avenue, Park Street businesses start pouring cocoa, and a line of decorated boats pulls away from the staging area by Fortman Marina. Plan around that half hour and the whole day goes smoothly.
10 a.m.: The Point first, because it closes at 6
Faction Brewing's Rock and Roll Flea Market runs from 10 a.m. to 6 p.m. at 2501 Monarch Street. It has 50 indoor vendors selling records, vintage clothing, handmade jewelry, musical instruments, tiki and Hawaiiana, and books. Admission is $5, and kids 12 and under get in free. The music lineup includes Deke Dickerson, Psycotic Pineapple, Surf Monster, Pollo Del Mar and Knights of Molino.
The market has run before. Faction held a holiday edition on December 7, 2024 and another market on July 26, 2025. This year it lands on the same day as everything downtown, which is why it belongs first on the list. It's the first of the five to close, and its 6 p.m. close comes half an hour after the yacht parade is due to start across the island. The Point gets your morning because it can't have your evening.
The indoor setup also makes it the safest bet if the weather turns. Rain matters less for the Point than for the waterfront.
1 p.m.: The Winter Market sets up off Park Street
The Downtown Alameda Winter Market runs from 1 to 7 p.m. It fills Central Avenue between Park and Oak, spreads across Parking Lot C, and continues onto Alameda Avenue. The Downtown Alameda Business Association promises music, twinkly lights, local artisans, gourmet food purveyors and food vendors. Its vendor application is still open, so the 2026 lineup is still coming together.
Last year gives a sense of the feel. The Alameda Post's recap of the 2025 market described live music all day, mixing carols, folk and pop covers, with musicians playing in front of the Alameda Theater.
The market's location matters for the evening. Central Avenue between Park and Oak is a short walk from City Hall at Santa Clara and Oak and from the Park Street storefronts. If you're browsing stalls at 4:45, you're already within a few blocks of two of the three sundown events. The third one, the parade, is on the water.
5 p.m. to 7 p.m.: Three starts, two parts of town
Here's the dusk window, laid out by clock:
| Time | Event | Where | Source |
|---|---|---|---|
| 5:00 to 6:00 p.m. | Winter Lights tree lighting | City Hall, 2263 Santa Clara Ave. | City of Alameda |
| 5:00 to 7:00 p.m. | Hot Cocoa Stroll | Downtown Park Street businesses | Downtown Alameda |
| Around 5:30 p.m. | Lighted Yacht Parade begins | Oakland–Alameda Estuary, from Fortman Marina | Lighted Yacht Parade |
| Until 7:00 p.m. | Winter Market winds down | Central Ave. between Park and Oak | Downtown Alameda |
Winter Lights. The City lists the celebration for 5 to 6 p.m. and says the page is being updated with 2026 details. The 2025 version, per the Alameda Post, drew hundreds of people who filled the block in front of City Hall to watch the tree light up. Performers included the Tap Dancing Christmas Trees, the Alameda Community Band and the Alameda Sings! Community Choir. Volunteers handed out free cookies for the Building Futures Jammie Drive, the Alameda Fire Department brought a decorated fire truck, and the Alameda Free Library gave away copies of The Snowy Day. Treat all of that as last year's program until the City posts this year's.
Hot Cocoa Stroll. It runs 5 to 7 p.m. and it's free. Participating businesses serve sips and nibbles while supplies last, and the 2026 list is due "soon." In 2025, more than a dozen businesses took part. Toy Safari handed out treats, SIGNAL Coffee Roasters brought back its Mexican hot chocolate and cookies, and lines formed outside the Alameda Cineplex and Daisy's Mercantile.
Lighted Yacht Parade. Boats gather between Wind River and the Fortman Marina public pier. Around 5:30 p.m. they head down the Alameda side of the Estuary, 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 and run back along it to the staging area. The organizers' FAQ says to expect the start "just after sundown," and the parade runs rain or shine. Its listed beneficiaries include the Alameda County Community Food Bank.
The route shapes your plan. Boats travel the Alameda shoreline on the way out and the Oakland shoreline on the way back. If you're watching from the Alameda side, the parade comes to you early in its run, close to the 5:30 start.
Picking your 5:30
Two of the three sundown events overlap, and the third overlaps both. The tree lighting ends at 6 and the cocoa stroll keeps going until 7, so City Hall and Park Street fit together nicely. Watch the tree come on, then walk to the storefronts for cocoa. That's how the Post described 2025: as it got dark, marketgoers moved toward Park Street for the stroll.
The parade is the one that won't move. It starts around 5:30, during the tree-lighting hour, and the Alameda-side pass comes early. Here are three ways to arrange the evening:
- Downtown all evening. Be at City Hall by 5 and stay through the lighting. After 6, work Park Street for cocoa and the market stalls on Central, since both wrap up at 7.
- Waterfront all evening. Leave the market in late afternoon and pick a spot on the Estuary. Organizers say you can watch from anywhere between Jack London Square and Fortman Marina on either side. A 2022 Alameda Post preview pointed to Pasta Pelican and the waterside windows and decks at the Encinal Yacht Club. Check current access before counting on either.
- Split the evening. Catch the parade's Alameda-side pass, then head downtown for the last stretch of the cocoa stroll. Cocoa runs while supplies last, so arriving late means fewer stops to choose from.
If you end up on Park Street after the stroll closes, UMe Tea held its grand opening on October 17 at 1321 Park Street, at Alameda Avenue. The Alameda Pulse lists its hours as noon to 8 p.m. daily, which keeps it open an hour past the last cocoa.
The rest of the season, by weekend
December 5 is the busiest day, but the holiday calendar starts this weekend.
- November 7 and 8: The 46th Alameda Holiday Boutique, 10 a.m. to 4 p.m., at 641 West Redline Avenue, run by Alameda Recreation and Parks.
- November 1 onward: The City's Alameda All Wrapped Up shop-local campaign, with 12 themed prize baskets. Downtown Alameda lists it through December 31, while the City's campaign page gives December 15, so check the deadline before you count on late receipts.
- November 28: Small Business Saturday, the Saturday after Thanksgiving.
- December 12: The West Alameda Business Association's Yule Midwinter Market, noon to 5 p.m. The venue hasn't been posted yet. ARPD's Breakfast With Santa is the same day.
- December 19 to 21: ARPD's Santa home visits.
I've lived through a lot of Alameda holiday seasons, and I'm always glad to share where I'd stand on December 5 or which Park Street stops are worth the line. If you're curious what your own home on the island is worth heading into the new year, Anne McKereghan offers a free home valuation, on your schedule and with no pressure.
