Pleasanton Upcoming Holiday Events Guide

The holiday season brings a warm, joyful glow to the San Francisco East Bay, and nowhere is that festive spirit more alive than in Pleasanton. Tucked in the heart of the Tri-Valley, this charming town sparkles with lights, laughter, and community cheer. From cozy evenings downtown to classic hometown celebrations, the holidays here are all about connection, gratitude, and creating moments to treasure.

Whether you’re visiting for the weekend or have lived in Pleasanton for years, this season offers endless ways to enjoy the town’s welcoming holiday charm. Gina Piper and her team at Elation Real Estate are delighted to share some of Pleasanton’s most beloved seasonal events that make this time of year truly unforgettable.

Small Business Saturday

Saturday, November 29

Kick off your holiday shopping by supporting local favorites on Small Business Saturday. Downtown Pleasanton transforms into a shopper’s paradise filled with cozy cafés, adorable boutiques, and one-of-a-kind finds. Every purchase helps the small businesses that make our city special. Pick up a “Support Local” tote at participating stores and enjoy a day of shopping, gratitude, and community spirit.

Magical Holiday Evening

Friday, December 5, 4 p.m. to 7 p.m.

Step into the holiday season at Pleasanton Downtown Association’s Magical Holiday Evening. Downtown becomes a glittering winter wonderland where families can take photos with Mr. and Mrs. Claus, meet Santa’s elves, and enjoy live festive music. Kids can create crafts, savor hot cocoa at the hot chocolate bar, and explore a cozy Christmas market featuring local artisans. It’s a heartwarming kickoff to the most wonderful time of the year.

Hometown Holiday Celebration

Saturday, December 6, starting at 5 p.m.

The Hometown Holiday Celebration is one of Pleasanton’s most cherished traditions. Main Street shines with lights, laughter, and holiday joy as a lively parade fills the streets. Colorful floats, marching bands, and local groups spread cheer for all ages. Afterward, gather near the Museum on Main for a festive tree lighting ceremony with music, performances, and a special visit from Santa himself.

Finding Frosty Scavenger Hunt

December 5–19

Enjoy a bit of playful fun during the Finding Frosty Scavenger Hunt. Pick up a map at Towne Center Books or Five Little Monkeys, then explore downtown shops to find hidden Frosty the Snowmen. Collect signatures, turn in your completed map to the Pleasanton Downtown Association office, and enter to win fun prizes. It’s a lighthearted way to experience downtown while making holiday memories with loved ones.

Holiday Window Decorating Contest

December 5–31

Downtown shop windows come alive with twinkling lights and creativity in the Holiday Window Decorating Contest. Take a stroll through Main Street to admire the festive displays, vote for your favorite, and soak in the charm of the season. Whether you’re window-shopping or sipping cocoa with friends, Pleasanton’s downtown is sure to dazzle at every turn.

Spirit and Sweater Stroll

Saturday, December 13, 5 to 8 p.m.

Slip into your coziest or most festive sweater for the Spirit and Sweater Stroll. Over fifteen downtown stops invite guests to taste seasonal cocktails and festive drinks while mingling with neighbors and friends. Start at the Museum on Main to grab your glass, wristband, and map, then explore downtown at your own pace. With music, laughter, and glowing lights all around, it’s a joyful way to toast to the holidays.

Final Thoughts

Pleasanton truly shines during the holidays, offering moments of joy, laughter, and togetherness that reflect the spirit of this wonderful community. From lively parades and twinkling lights to cozy nights downtown, each tradition reminds us of the warmth that makes this city so special.

If you find yourself falling in love with the charm of this vibrant town, Gina Piper and her team at Elation Real Estate are here to help you discover the perfect place to call home. Whether you are exploring homes for sale in Pleasanton or looking to settle in one of the nearby Tri-Valley communities, Gina and her team would be honored to guide you home for the holidays and beyond. Contact us today.

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