B Street Is Becoming Downtown San Mateo's Stage. The Everyday Counters Are Moving Around It.

For 25 years, the glazed doughnuts and bear claws at Donut Delite on B Street were part of the downtown routine. In September, a letter went up in the front window. "We are truly grateful for the memories and relationships we have made," it read, as quoted by the San Francisco Chronicle. The shop closed after the property owner sold the building, and the site is slated to become a four-story building.

A building sale cleared one of B Street's longest-running counters. More and more, the stretch of B Street between First and Third avenues is a place the city and the Downtown San Mateo Association program by the date: a market here, a trick-or-treat afternoon there. The everyday counters are reshuffling around it, especially on Third and Fourth avenues. If you live here, it helps to know which is which, because the calendar and the storefronts now change on different schedules.

The site on B Street that won't reopen as it was

The Donut Delite block runs from 31 to 57 S. B St., and the City of San Mateo already tracks it as a commercial mixed-use project. The San Mateo Daily Journal described the replacement as a four-story building of about 41,200 square feet for retail, restaurants and offices, with completion expected in 2027.

So the doughnuts aren't gone for good, and neither is the operator. Owner Sung Khov runs two other Donut Delite locations, in Redwood City and Menlo Park, and told the Daily Journal he hopes to find a nearby space at a more affordable price. For now, the closest Donut Delite counters are a drive away. The B Street site enters a construction phase likely measured in seasons, not weeks.

Third and Fourth avenues are where the new counters are landing

While one long-running B Street counter closes for redevelopment, new food is opening in the storefronts just off it. Most of these openings take over existing spaces, so the change shows up as new signs on familiar doors.

The Roma Antica timeline has moved once already. On Aug. 19, Palo Alto Online reported a late-September opening for 172 E. Third Ave. Two days later, WhatNow reported that the team was training staff, aiming for October, and hadn't finalized a date. Before you plan a dinner around it, check whether the doors are open.

Pineapple King Bakery is the one to watch as the holidays get closer. The Almanac's September roundup puts its opening in December at 145 E. Third Ave., the former Shabuway space, with no specific day yet. The same roundup lists Auntea Jenny for 253 S. B St., in the former Hereetea, also without a date. On Fourth Avenue, OOOTea at 165 E. Fourth Ave. ran a one-day, 20% anniversary promotion on Aug. 22.

Turnover reaches past the core blocks, too. Hey Yogurt held a soft opening Aug. 25 through 30 at 310 S. San Mateo Drive. According to the DSMA's October 2026 newsletter, Thonglor Thai Bistro is under new ownership and is offering a weekday lunch special.

The counters that stayed are changing when they're open

The established spots on B Street are changing what they serve and when. That is a quieter kind of turnover. Rise Woodfire at 2 N. B St. launched its Rise & Shine weekend brunch and Daily Dose Coffee Bar with a public grand opening on Sept. 26. Brunch now runs Saturdays and Sundays from 9:30 a.m. to 2 p.m.

The October newsletter lists more of these small shifts. Pausa has a new bar menu, served until 6 p.m. in the bar area and outside and all day at the bar. Tai Er added weekday lunch combos, from 11:30 a.m. to 2:30 p.m., at $25 for one and $55 for two. Fish With You is serving roast duck. Blue Moon Bar added Bar Bingo on Tuesdays from 6 to 8 p.m. A weekday lunch or a Tuesday night downtown now has options it lacked in September, behind the same storefronts.

The business that has outlasted every turnover sits off the main strip

Takahashi Market has been at 221 S. Claremont St. long enough to celebrate its 120th anniversary this fall. DSMA listed the Sept. 27 celebration in the market's front parking lot, with performances, food and vendor booths. At that event, according to the Consulate General of Japan in San Francisco, Deputy Consul General Takeshi Ishihara presented the market with the Consul General's Commendation for its contribution to Japan–California relations.

Against a 25-year doughnut shop and a string of new arrivals still waiting on opening dates, 120 years on Claremont Street makes clear how unusual that kind of run is downtown. It is also a good reason to walk a block past B Street now and then.

How B Street gets booked between Halloween and New Year's

The city and the DSMA program the B Street pedestrian mall between First and Third avenues by the date. The City of San Mateo Parks and Recreation Department and the DSMA scheduled Boos and Brews on B Street for Saturday, Oct. 24, from 3 to 5 p.m., with trick-or-treating, arts and crafts, a reptile petting zoo, music, and food and drinks. HEAD WEST Marketplace comes back to the same stretch on the third Saturday of each month.

The holiday rink is the season's biggest fixture, and it sits in Central Park, not on B Street. San Mateo on Ice runs from Nov. 13, 2026, through Jan. 10, 2027, on an outdoor rink with 11,000 square feet of real ice. The rink's public skate page lists $20.33 per skater, skates included. The operator's site also lists free community skate days on Nov. 16, Dec. 1, Dec. 8 and Dec. 10.

Here's the calendar from Halloween through the December market:

1. Saturday, Oct. 31: Doggoween returns to the Fieldwork Brewing San Mateo beer garden in Bay Meadows Town Square from noon to 2 p.m., with a dog costume parade and a contest decided by public vote. Pinstripes at Hillsdale Shopping Center hosts a Halloween Kids Party the same day.
2. Through Friday, Nov. 13: Bay Meadows' Cans for Change food drive collects canned goods for the San Francisco-Marin Food Bank at The Russell leasing office, 3098 Kyne Street West.
3. Sunday, Nov. 8, Wednesday, Nov. 11, and Saturday, Nov. 14: Pinstripes at Hillsdale holds Brunch & Burn, a pizza-making class and Kids Club.
4. Friday, Nov. 13: San Mateo on Ice opens in Central Park.
5. Saturday, Nov. 21: HEAD WEST Marketplace runs on B Street between First and Third avenues, 11 a.m. to 4 p.m.
6. Saturday, Nov. 28: The Bougie Brunch at Golden Moon Studios.
7. December: Pineapple King Bakery's expected opening at 145 E. Third Ave.
8. Saturday, Dec. 19: HEAD WEST Marketplace comes back to B Street, 11 a.m. to 4 p.m.

Planning a December Saturday around the market and the rink

The way these pieces fit together is practical. A December Saturday can start at the HEAD WEST Marketplace on B Street and move to the rink in Central Park, with a stop on Third Avenue in between if Pineapple King has opened by then. The rink stays open until Jan. 10, so the season runs past the holiday markets and well into the new year.

Meanwhile, the block where Donut Delite stood for 25 years is headed for a building expected in 2027. When it's finished, the new restaurant and retail space will add one more storefront to the reshuffling.

If you'd like to talk about how these new arrivals and the 2027 building on B Street fit into your plans, I'm always happy to compare notes over coffee downtown. Let's Connect with Julie Baumann.