Date ideas in Santa Clara County: 31 picks from the Santa Clara County guide, each linked to its source. Details can change. Check with the venue before you go.
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Outings near you
For a date with a story behind it, the Winchester Mystery House in San Jose was built over nearly four decades beginning in 1886 and is known for its maze-like architecture. Theater nights, museum evenings and other plans for two in Santa Clara County follow. Source: winchestermysteryhouse.com
Date ideas in Santa Clara County
Evenings out, scenic spots and shared experiences for two.
Everyone at SJMA's First Fridays can enjoy an inviting evening with open galleries and entertainment; late-night bites and a cash bar at El Cafecito, by Mezcal Restaurant. Register in advance for fast check-in.
Opening celebration of Irving Norman: Fight for Life, a focused survey of the late Bay Area artist known for monumental paintings critiquing the perils of modern life, with live music by The Brian Fitzgerald Trio. Register in advance for fast check-in.
Create a colorful acrylic pet portrait inspired by Andy Warhol, guided step by step by artist Mai Blasich; no experience needed, all materials provided. Indoors, limited to 10 participants; email a photo of your pet ahead of time.
Tradition meets revolution in Opera San Jose's new production of Fiddler on the Roof, with Eugene Brancoveanu in his role debut as Tevye. Doors open 12:30 PM for matinees and 6:00 PM for evening performances; preshow discussion at 1:00 PM and 6:30 PM. Passenger loading zone directly in front of the theatre entrance.
Dates
November 15 - November 29, 2026 (Sun Nov 15, Fri Nov 20, Sun Nov 22, Sat Nov 28, Sun Nov 29)
In 1969, The Who created a rock opera that changed the course of music history, and now it's back in a dazzling all-new production with "I'm Free," "See Me, Feel Me," "Sensation" and "Pinball Wizard." Recommended for ages 16+. 100 minutes with no intermission.
Fortino Winery's 23rd Annual Fall Market on Hecker Pass, with vendors, music by Carlos Padilla, food from California Inspirations and coffee from Taaza Coffee.
A strenuous 6-mile evening hike up the Canyon and Bella Vista trails to watch the sunset and full moon rise from Black Mountain's summit; bring your own food. Reservations open November 10 at noon.
Stroll the Historic Saratoga Village for an evening of wine tasting, live music by Kurt & Johnny and holiday cheer, hosted by the Saratoga Chamber of Commerce. Tickets are limited; rain or shine.
Nothing says the holiday season has arrived like hearing the voice of Karen Carpenter singing "Merry Christmas, Darling." This all-new production brings the brother-sister duo's unforgettable music back to the stage. 2 hours and 20 minutes, including a 20-minute intermission.
A remixed Nutcracker smashing hip hop dance and Tchaikovsky, with a dozen all-star dancers, a DJ, a violinist and MC Kurtis Blow opening the show. Grab your family and friends; about 2 hours with intermission. All guests entering the theater, regardless of age, must have a ticket; no lap seats.
Singer Debbie Taylor leads this Carpenters tribute band through the duo's greatest hits and the stories behind the music, without backing tracks, in Montalvo's Carriage House Theatre. ADA seating and parking available.
An evening of live music, storytelling and drag performances kicks off the holidays and celebrates the talents of San José's LGBTQIA+ community, with open galleries and free admission after 6pm.
Nathan Aspinall conducts Wagner's Siegfried Idyll, first performed on Christmas morning, Respighi's Trittico Botticelliano and Mozart's Symphony No. 39, with carolers in the lobby before the concert. Approx. 1 hr 50 min. with intermission.
Dates
Saturday, December 5 and Sunday, December 6, 2026
Hours
Saturday 7:30 p.m.; Sunday 2:30 p.m.
Cost
Single tickets from $35 (fees included); prices vary with demand
Jazz pianist David Benoit, longtime composer for the Peanuts TV specials, pays tribute to Charlie Brown with his own Christmas originals and the beloved Vince Guaraldi classics in the Carriage House Theatre. ADA seating and parking available.
A live-to-film concert of Richard Curtis' Christmas classic: a live orchestra performs the film's soundtrack, featuring Mariah Carey's "All I Want for Christmas Is You" and Craig Armstrong's score. Recommended for ages 17+. 2 hours and 42 minutes, including a 20-minute intermission.
An evening of analog games at SJMA: learn new games and make new friends, or bring your own analog games to share. Free admission after 6pm; cash bar at El Cafecito.
Tatsuya Shimono conducts Daugherty's American Gothic, Ravel's Piano Concerto in G Major with Jon Nakamatsu, and Mussorgsky's Pictures at an Exhibition (arr. Ravel). Approx. 1 hr 50 min. with intermission.
Dates
Saturday, January 23 and Sunday, January 24, 2027
Hours
Saturday 7:30 p.m.; Sunday 2:30 p.m.
Cost
Single tickets from $35 (fees included); prices vary with demand
From the creators of Avatar: The Last Airbender in Concert: celebrate 15 years of The Legend of Korra with a live symphonic performance. 2 hours, including an intermission. All guests entering the theater, regardless of age, must have a ticket. No lap seats.
Based on the 1992 film starring Whitney Houston and Kevin Costner, THE BODYGUARD is a thrilling, romantic musical featuring "I Wanna Dance with Somebody" and "One Moment in Time." Recommended for ages 13+. 2 hours 10 minutes, including a 20-minute intermission.
John Adams's Doctor Atomic in an all-new production chronicling the moral and emotional turmoil surrounding the Manhattan Project, conducted by Maestro Joseph Marcheso. Doors open 12:30 PM for matinees and 6:00 PM for evening performances; preshow discussion at 1:00 PM and 6:30 PM.
Dates
February 14 - February 28, 2027 (Sun Feb 14, Fri Feb 19, Sun Feb 21, Fri Feb 26, Sun Feb 28)
The touring production of the musical comedy Mrs. Doubtfire, based on the film, about an out-of-work actor who will do anything for his kids. Recommended for ages 8+. 2 hours 30 minutes, including a 20-minute intermission.
An immersive concert-style theater show chronicling the journey of Paul Simon and Art Garfunkel, with huge projection photos, original film footage and a full live band performing hits including 'Mrs. Robinson' and 'Bridge Over Troubled Water'. 2 hours and 15 minutes, including one intermission.
Section: Date ideasevent
