• Magical Memories Holiday: Trolley Rides & Visits with Santa

    *Complimentary with No Reservations Needed*

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    Announcing the return of our Magical Memories Holiday Program, made possible through the generosity of our sponsors, especially Presenting Sponsor, Linda Lester of Lester Square! Los Gatos’ newest tradition centered around Trolley Rides, Visits with Santa, Gourmet Hot Chocolate Sips and Sweet Surprises —brings joy, connection, and delight to families across our community. The experiences are free of charge, with no reservations required. Last year, we served over 800 families and 1,300 children. Watch our Magical Memories 2024 Highlights reel here.

     

    Share the Care!

    If you love Magical Memories, please donate to our official 2026 charity partner: Rebekah Children’s Services, providing mental health, foster care and adoption services in Santa Clara County. The purchase of a keepsake Magical Memories mug at Santa's Workshop or at the Chamber store at 10 Station Way also supports our program.

    While you’re downtown for Magical Memories, enjoy exciting perks and offers across our shops, restaurants and services, with a complimentary Los Gatos Perks Pass. This free mobile pass (no app needed) is ideal for both visitors and locals and is good through July 31, 2026.

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    Trolley Rides

    Saturday, December 6  (4 to 8 pm)
    Sunday December 7  (1 to 5 pm)
    Friday, December 12  (5 to 8 pm)
    Saturday, December 13  (1 to 5 pm)
    Sunday, December 14  (1 to 5 pm)
     
     
    Climb aboard our cable car style trolley and enjoy a unique experience with your friends and family. The Trolley will follow a scenic hop on/hop off loop through our beautiful downtown (about 15-20 minutes). To ensure the maximum number of guests experience this amenity, please limit your ride to one full loop. See below map for route and stops. Youth under 16 years of age must accompanied by an adult on the trolley. Our volunteers will be on hand to assist at the Town Plaza Park stop.
     

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    Visits with Santa

    Friday, December 12  (4 to 7 pm)
    Saturday, December 13  (1 to 6 pm)
    Sunday, December 14  (12 to 5 pm)
     
    Santa will greet children of all ages in his festive workshop at Old Town Los Gatos for three magical afternoons of visits filled with holiday cheer. Our Los Gatos Rotary elves will be on hand to help take photos on your phones. Enjoy live entertainment including holiday characters and music in the first-come, first served queue. There’s an Old Town trolley stop to make joining in on the fun easy. Upon departing the workshop, one holiday goodie bag (while supply lasts) awaits each family. Courtesy of Presenting Sponsor, Lester Square, these goodie bags,* are filled with fresh mini Icing on the Cake Cookies as well as other treats.
     
    To help Santa get back to the North Pole on time, we may close the workshop queue up to 30 minutes before the posted closing time if the wait reaches 30 minutes. Please plan ahead so we don't miss your visit. Also, to ensure the maximum number of families experience this complimentary amenity, visits are intended to be brief. Thank you for your understanding. *One goodie bag per family, while supply lasts.
     

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    Gourmet Hot Chocolate Sips

      

     
    Friday, December 12  (5 to 7 pm)
    Saturday, December 13  (2 to 4 pm)
    Sunday, December 14  (2 to 4 pm)

     

    Courtesy of our Magical Memories sponsors, warm up with a 4oz cup of rich, gourmet hot chocolate scratch-made with love (as well as dark chocolate, milk chocolate, white chocolate, and cream!) by Breaking Dawn/ First Born Restaurant. Stop by the First Born parklet for a taste during these times, while supply lasts. To ensure the maximum number of people enjoy this amenity, we are offering one cup per person.

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    Magical Memories Sweet Surprises Tent

    Saturday, December 6  (3 to 5 pm)
    Sunday December 7  (3 to 5 pm)
    Friday, December 12  (3 to 5 pm)
    Saturday, December 13  (3 to 5 pm)
    Sunday, December 14  (3 to 5 pm)

     

    Stop by our Magical Memories Sweet Surprises tent in the breezeway next to Automobuild (100 N. Santa Cruz Ave.) before or after your Visit with Santa or Trolley Ride, where one of our wonderful sponsors (Good Samaritan Hospital, West Valley College, and El Camino Health) will be onsite giving out family-friendly surprises from 3 to 5 pm (or until supply lasts). Due to limited quantities, we ask that each person be present to receive a surprise.

     

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    Trolley Route

    Hop on/ Hop off at the four stops marked by Trolley icons
    Youth under the age of 16 must be accompanied by an adult.
     
     

  • Thank You to our Sponsors 

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    Presenting Sponsor

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    Chamber Title Sponsors

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    Signature Sponsors

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    Spirit Sponsors

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    Supporting Sponsors

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    Charity Partner

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    Magical Memories Elves

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    2025 Chamber Title Sponsors

         

     

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