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The Pleasanton Downtown Association has unveiled its schedule of special events for the year, saying that “creating shared experiences, strengthening community connections and supporting small businesses” is at the heart of the series of familiar and new offerings alike.
Headlining the lineup are the summer Concerts in the Park at Lions Wayside Park, two installments of Weekends on Main taking over Main Street and popular holiday showcases like the Bunny Hop Hunt, Halloween Brew Crawl and Spirit & Sweater Stroll. New additions are the inaugural Country Fest in June and the first Boo Bash for the whole family in mid-October.
“Designed to bring people together in Downtown Pleasanton, these events welcome residents, visitors, and guests from across the region to gather, connect, and support the local small businesses that make downtown such a vibrant and inviting destination,” PDA Executive Director Gabrielle Welk said in the press release last Friday.
“Whether you’re a longtime local or visiting Downtown Pleasanton for the first time, the 2026 event lineup invites everyone to stroll Main Street, discover unique shops and restaurants, enjoy live entertainment, and experience the joy of coming together — right in the heart of the city,” Welk added.
Leading things off will be annual St. Patrick’s Day Brew Crawl “featuring festive pours, green gear and plenty of Irish cheer” on March 14. Next up will be a pair of springtime favorites: the Bunny Hop Hunt on April 4 and the Wine Stroll on May 2.
Weekends on Main, which see Main Street closed to vehicular traffic from 4 p.m. Friday through 10 p.m. Sunday, return June 5-7 for the first of two installments. The Saturday (June 6) will offer Hot Rod Row while the Sunday (June 7) will bring Totally Mimosa and the first-ever Country Fest.
“Main Street transforms into a full-blown country playground with 4+ live band stages featuring country artists all day long, a BBQ smoker cook-off, corn hole tournaments, line dancing, a petting zoo, and local vendors lining the street,” PDA officials said of Country Fest.
Concerts in the Park return on Friday evenings from June 5 to Aug. 28 – with the band roster still to be released.
The Forkful Culinary Crawl showcases downtown’s diverse dining scene Sept. 12.
Weekends on Main are back from Oct. 2-4, including Pleasanton Palooza and the BMX Bike Fest on the Saturday (Oct. 3) and Porsches on Main on the Sunday (Oct. 4).
PDA will debut its new Boo Bash – “the grand finale of the month-long Pumpkins on Main Scavenger Hunt” – on Oct. 17.
“Families are invited downtown for an afternoon of Halloween music, festive carnival games, a pumpkin painting contest and fall fun,” PDA reps said. “Downtown businesses will also be open for trick-or-treating, giving kids another chance to fill their bags with goodies. Costumes encouraged — spooky and sweet fun guaranteed.”
Four popular returning events will round out the 2026 schedule for the PDA: Halloween Brew Crawl on Oct. 24, Small Business Saturday on Nov. 28, Magical Holiday Evening on Dec. 4 and Spirit & Sweater Stroll on Dec. 12.
To learn more about each event and the rest of the PDA’s activities, go to pleasantondowntown.net.
