Pleasanton Upcoming Festive Season Events

November 8, 2025

The holidays bring a special kind of magic to the San Francisco East Bay, and nowhere is that spirit more alive than in Pleasanton. Nestled in the heart of the Tri-Valley, this charming city glows with festive lights, joyful gatherings, and a sense of community that shines bright all season long. From hometown parades to cozy evenings downtown, the holidays in Pleasanton are all about connection, celebration, and creating memories that last.

Whether you are visiting for a day or have called Pleasanton home for years, the season offers countless ways to experience its warmth and wonder. The Elation Real Estate team is delighted to highlight some of the most beloved local traditions that make this time of year so special.

Small Business Saturday

Saturday, November 29

Downtown Pleasanton comes alive with local pride on Small Business Saturday. Stroll along Main Street and discover charming boutiques, cozy cafés, and one-of-a-kind gifts that make Pleasanton’s downtown so special. Every purchase supports the small businesses that give our city its heart and character. Pick up a complimentary “Support Local” bag at participating shops and enjoy a day filled with gratitude, community spirit, and holiday cheer.

Magical Holiday Evening

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

Kick off the holiday season with the Pleasanton Downtown Association’s Magical Holiday Evening, a celebration that transforms downtown into a sparkling winter wonderland. Families can enjoy free photos with Mr. and Mrs. Claus, meet Santa’s cheerful elves, and listen to live holiday music. Children can join in festive crafts, sip warm cocoa at the hot chocolate bar, and explore a charming Christmas market filled with local vendors. It’s a night that captures the joy and wonder of the season.

Hometown Holiday Celebration

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

Experience the magic of Pleasanton’s beloved Hometown Holiday Celebration, where Main Street glows with lights, laughter, and community spirit. The evening begins with a spectacular parade featuring colorful floats, marching bands, and local organizations spreading cheer. As the parade concludes, gather by the Museum on Main for a heartwarming tree lighting ceremony with music, performances, and a visit from Santa. This cherished tradition truly embodies the heart of the holiday season in Pleasanton.

Finding Frosty Scavenger Hunt

December 5 to 19

Gather your family and friends for a playful adventure through Downtown Pleasanton during the Finding Frosty scavenger hunt. Pick up a map at Towne Center Books or Five Little Monkeys, then set off to locate Frosty the Snowman hidden in participating shops. Collect signatures as you go, and return your completed map to the Pleasanton Downtown Association office for a chance to win exciting prizes. It’s a festive way to explore, connect, and share holiday smiles.

Holiday Window Decorating Contest

December 5 to 31

Take in the beauty and creativity of the season during Pleasanton’s Holiday Window Decorating Contest. Downtown shops transform their storefronts into twinkling works of art, each display telling its own holiday story. Pick up a map, enjoy a festive stroll, and vote for your favorite by scanning the QR code on the window. Whether you’re admiring the lights or window-shopping with cocoa in hand, downtown will dazzle at every turn.

Spirit and Sweater Stroll

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

Slip into your coziest or most festive sweater and join the merriment at the Spirit and Sweater Stroll. More than fifteen downtown stops invite guests to sample handcrafted cocktails and seasonal sips in a lively, cheerful atmosphere. Check in at the Museum on Main for your glass, wristband, and map, then explore at your own pace. With music, laughter, and twinkling lights all around, it’s the perfect evening to toast to the season with friends.

Final Thoughts

From luxury real estate in Pleasanton, Livermore, and Danville to charming homes in Dublin, Alamo, Alameda, Walnut Creek, Oakland, and Berkeley, Elation Real Estate is proud to serve communities where life is rich with celebration and connection.

For us, the holidays are about more than decorations and events. They are about local traditions passed through generations, and the comfort of gathering with loved ones in a space that feels truly yours.

If you are considering buying or selling in the San Francisco East Bay, including the Tri-Valley, contact Elation Real Estate today. Let our team help you find your perfect place to call home, where every season brings new reasons to celebrate.