Cherry Festival

The day begins at ten in the morning near the South Parking Lot of the San Leandro BART station. The Cherry Parade forms there, turns down Parrot Street and up East 14th Street, and runs just under a mile to the San Leandro Main Library on Estudillo Avenue. Community organizations and local businesses ride floats, drive classic cars, and walk in costume. The streets along the route are closed to traffic from 8 a.m. to noon. The 2026 edition was held Saturday, June 6. The parade ran an hour, and at eleven the crowd moved a few blocks over to the festival.

West Estudillo, the Boulevard to Hays

The festival fills West Estudillo Avenue in the historic downtown, between San Leandro Boulevard and Hays Street, until 6 p.m. The vendor market runs to more than 150 booths. Artisans sell handcrafted goods and packaged cherry foods to take home. Interactive booths offer face painting, sand art, wax hands, spin art, ring toss, and a spin-the-wheel. Nonprofit agencies hand out information on volunteering, health, schooling, faith groups, and the arts. There is also a fresh cherry market, a family fun zone, and beer and wine. Classic cars stand parked for the whole afternoon in the car show, which is open to vehicles from 1980 and older. The 2026 show was its fourth annual. No loud music is allowed from the cars.

There are two stages. On the community stage, local groups and individuals perform without pay. The 2026 main stage opened at 12:15 with Farenhyte5150, a Bay Area R&B and funk band. Conjunto Karabali followed at 2:15 with Mike Spiro and the percussionist Karl Perazzo, billed as a fourteen-time Grammy winner. The Purple Ones, “California’s Premier Prince Tribute Band,” played from 4:15 to 5:45.

The festival is hosted by the Downtown San Leandro Community Benefit District, a nonprofit formed in 2013 and supported by downtown property owners. The City of San Leandro and its Recreation and Parks Department also appear as hosts. The district counted more than 30,000 people at the 2025 festival, using geofence data.

Cherry on every menu

Food vendors cook on the street under a firm rule: every one must carry a cherry or cherry-themed item. Approved menus are “strictly enforced,” and the City tries to limit how many vendors sell the same dish. Cecilia Phillips of KQED’s Check Please! Bay Area came to the festival for an episode on KQED 9. She sampled cherry carnival lemonade, cherry ice cream sundaes, cherry-rosemary focaccia, and maraschino cherry cupcakes.

Lattice tops and a three-by-five card

Pies for the baking contest go to the Pie Contest Booth between 11:00 and 11:30 in the morning, and late entries are refused. Crust and filling must both be homemade. The pie comes in a dish the baker will not get back, with the recipe written on a 3-by-5-inch index card. Judges score tasting and presentation in three categories:

• Traditional: a crust filled with cherries under a lattice or plain top.
• Non-traditional: a variation on cherry filling and crust, with toppings, fillings, and crusts free to vary.
• Youth: open to bakers 13 and younger.

In 2026 Linda Rexrode took first place in traditional and Julia O’Roarke second. Henry David won non-traditional, with Madie Weiland second. Nadav Gilbert won the youth category and also Best in Show overall.

The pie-eating contest crowns a cherry pie champion. The first was Latu Fanaika, who, in the organizers’ words, “made history” on Saturday, June 3, 2023, as San Leandro’s first pie-eating champion.

The Cherry City, 1909

The ground under the festival was Jalquin Ohlone country before it became part of José Joaquin Estudillo’s Rancho San Leandro, a cattle ranch. Gold Rush squatters arrived in the 1850s. San Leandro served as the seat of Alameda County from 1855 to 1873, then took a quieter path once the seat moved to Oakland. Farmers found they could grow almost anything on the flatlands, and bay access and early railroads carried the produce to distant markets. The town had dairies, chicken ranches, wheat, and vegetables, though orchards covered much of the land.

According to the San Leandro Historical Society, in 1909 the town decided to hold a cherry festival to celebrate a bumper crop of cherries. The festival established San Leandro as the Cherry City. “Cherry festivals have been held off and on ever since,” the Society writes.

The town carried other names in the same years. Settlers from the Azores, joined in the 1890s by Portuguese sugar workers left jobless by depression in Hawaii, earned it the title “the Portuguese Capital of the West.” By the late 1800s it also had factories making tractors, combines, and hay presses, along with a cannery. San Leandro remained the Cherry City until floriculture began to replace farm fields. In the 1930s it called itself the City of Sunshine and Flowers.

World War II brought thousands of newcomers, and the population kept growing through the 1950s and 1960s. Farm fields were sold to developers for housing, and the town began billing itself as the “City of Industry.” Housing discrimination at first shut out African Americans, Asian Americans, Hispanics, and Latinos. After California’s Rumford Fair Housing Act took effect, San Leandro became, in the Society’s account, one of the most diverse cities in the state. Of the old landscape, the Society records: “The elk and grizzlies, the vast cattle ranches, and the cherry orchards are gone.”