How To Spend Christmas In Willow Glen, A Bubbly San Jose Neighborhood

This post is all about Willow Glen, a San Jose neighborhood known for its holiday magic, bubbly neighborhood walks, and swanky restaurants.

Willow Glen, a district in San Jose, was originally its own town until a vote resulted in it being annexed by San Jose in 1936. Not known to most non-Bay Area residents, when someone familiar with it asks where I grew up, and I answer Willow Glen, I usually get a “oohhh” response with a familiar nod or eyebrow raised, like I said something exotic or remote like the North Pole.

I lived in the same modest house through adulthood, and while much has changed over the years, a lot has stayed unchanged. Willow Glen remains one of the most expensive San Jose neighborhoods to live in (as well as businesses to lease in).

a woman holding a gingerbread house to represent the author, Tina Casalino, growing up in a home in a holiday town

The center of Willow Glen continues to revolve around its charming downtown area featuring Lincoln Ave., the main thoroughfare.

Locals love to frequent numerous events throughout the year, including wine walks and farmers’ markets, as well as locally-owned businesses from salons and barber shops, eclectic vintage and consignment stores, and children’s bookstore Hicklebee’s.

downtown Willow Glen — photo by Tina Casalino

And, of course, the food scene, a flourishing sea of independent, family-friendly sidewalk café-style restaurants with umbrellas lined up from one end of the street to the other, unique with diverse menus and cuisines, lots of lit-up signs, and plenty of outdoor seating.

Here’s our guide to Willow Glen, San Jose, a charming Bay Area day trip getaway (especially during the holidays)!

Table of Contents

Willow Glen, San Jose Travel Guide

Willow Glen Town Square — photo by Tina Casalino

Willow Glen Architecture

Stepping away from the bustling downtown area, and looking closer at Willow Glen’s residential neighborhoods, not every house looks like it belongs in Disneyland’s Storybook ride (a common misconception). While there is a section of town off Lincoln Ave. that features many enchanting storybook-style homes, visitors will find a variety of architecture, including cottage-style, Tudor bungalows, and mid-century modern Eichlers (also known as California Modern) that feature glass walls, lots of beams, and atriums.

Some houses are none of these styles, though, and it’s become common to tear down and reconstruct older homes to feature more modern-day luxury styles. If House Beautiful is your magazine of choice, you could make a day out of driving around the many avenues here, admiring beautifully manicured front yards, A-lined trees, and the diversity of architecture.

Best Time To Visit

holiday lights display at Willow Glen — photo by Tina Casalino

Any time is excellent to visit Willow Glen, but it’s most magical during December. It’s not just me who thinks so – I asked over fifty Willow Glen residents what they loved most about Willow Glen, and the holidays came up an overwhelming amount of times!

From small, decorated Christmas trees lining the front yards of many streets to over-the-top holiday displays to large, illuminated snowflakes hanging from trees, to a large display of Santa and his reindeer with a brightly-colored sleigh showcase spanning for a few houses on one street, the holidays are not to be missed in Willow Glen!

Willow Glen neighborhood lights display from one of the homes in Willow Glen — photo by Tina Casalino

Also unique to the season is a 30-minute cable car ride (December 8th through 19th) around the most animated avenues and downtown’s annual Holiday Bubbly Walk (December 7th) for an afternoon of wine and shopping.

Travel Tip: Festive décor is Willow Glen, but for some of the most spectacular lights, head to Willow Street Frank Bramhall Park and follow the lights! Park and walk, especially on weekends when traffic is the most congested (but bring flashlights and reflective clothing for visibility). And, look online for possible Santa appearances – he usually makes several stops in Willow Glen, including on Lincoln. He has also been spotted hanging out at various houses throughout the neighborhood.

Things To Do In Willow Glen San Jose

photo of glasses filled with sparkling wine clinking, to represent Willow Glen Bubbly Walk, one of the seasonal wine walks in Willow Glen — photo by Artem Kniaz

Whether you’re visiting specifically for one of Willow Glen’s holiday events, or just want to check out different options for activities, there’s plenty to choose from (across the year). Here are some ideas to help plan your itinerary.

Travel Tip: A car isn’t necessary to visit Willow Glen but is nice if visiting multiple areas. Assuming you’re starting downtown, there are plenty of free two-hour parking spots on Lincoln Ave, numerous parking lots behind businesses, and parking spaces on surrounding residential streets seconds away.

Seasonal Activities

Holiday Bubbly Walk: Cheers to an evening of sparkling wine tastings along Lincoln Avenue.
Spring Wine Walk: If you’ve always wanted to combine wine and shopping, and missed the Holiday Bubbly Walk, you can attend the Spring Wine Walk.
Music In The Glen: This annual concert series begins each summer at Willow St. Frank Bramhall Park. Lawn seats and blankets are welcome.
BBQ in the Glen: Love BBQ? BBQ In The Glen, an annual team-based BBQ competition, takes place every September.

Things To Do In Willow Glen This Weekend

little free library in Willow Glen neighborhood

photos (left, right) by Tina Casalino

Willow Glen Farmers’ Market: Here on a Saturday morning? Who doesn’t love a farmers’ market, where local small businesses sell everything from seafood and coffee to the freshest flowers, fruit and vegetables.
Little Free Library Tour: Many homeowners (on residential streets) have built charming little free libraries and placed them in front of their houses. The concept is simple – take a book, leave a book. If you love to read, gather all the books you’ve finished, didn’t like, etc. and bring them with you to disperse around town, and pick up some new ones!

Where To Gift Shop In Willow Glen

Petroglyph Ceramics, one of the best things to do in Willow Glen — photo by Tina Casalino

Petroglyph Ceramic Lounge: Feeling crafty? Head inside to Petroglyph Ceramic Lounge where you can create a gift for you or someone you love, or even a souvenir of your time spent in Willow Glen!
Glow Candle Lounge: Continue the DIY experience at Glow Candle Lounge where you can absorb the most heavenly scents while indulging in candle-making.
Hicklebee’s: One of the most popular children’s bookstores in California, Hicklebee’s has been around since 1979. Check out their event calendar to see what events and local authors may be there during your visit.

Travel Tip: If you love hunting for treasures, there are many to be found at multiple antique shops, vintage boutiques and thrift stores on Lincoln. Willow Glen Collective is great for nostalgia and Thrift Box is my favorite because it benefits Lucile Packard Children’s Hospital Stanford and is a volunteer-run store.

Where To Eat In Willow Glen San Jose

Willow Glen Restaurants featured image — photo by Tina Casalino

Are you hungry? You certainly will be once you start walking around downtown. You might think everything in Willow Glen is condensed to Lincoln Ave. since it’s the main downtown hub, but there are many other streets, areas and shopping centers (with great food) that shouldn’t be missed.

Breakfast

The Table : Start out the day at American restaurant The Table (corner of Willow and Lincoln) and sit outside for people-watching (and sidewalk cafe ambiance) while enjoying coffee, mimosas and brunch options like chilaquiles.
Toast Café & Grill: Toast is a spot locals love to hit up for breakfast. I just went for the first time and tried the carnitas skillet, a hearty portion of carnitas and country-style potatoes underneath two eggs of your choice and covered with cheese and salsa and served with…toast of course!

Lunch

Willow Glen San Jose downtown dining option, where green and red Christmas lights are strung up over outdoor eating area — photo by Tina Casalino

Bertucelli’s La Villa Gourmet: Expect standing room only for ordering (but a large outdoor seating area) and a crowd and a line for the most amazing Italian deli in all of San Jose! Order their world-famous raviolis which you can opt to get with cheese or beef, sauce or no sauce, cooked or uncooked (if you want to take it and cook later).
Giorgio’s: A family-owned Italian restaurant, Giorgio’s has served customers since 1959 on their tables decorated with red and white checkered tablecloths, offering diners many Italian favorites including pizza, pasta and calzone.
Mexico Lindo: Known for delicious Mexican dishes, The Original Mexico Lindo Restaurant has also been a staple in the community for more than 35 years (there are other Bay Area locations, but their Willow Glen spot remains iconic).

Travel Tip: Looking for dessert? Enjoy delicious gelato at Dolce Sicilia, grab donuts from Manley Donuts, try the signature “St. Louis silk” frozen custard at Willow Glen Creamery, or pop into El Rico Pan bakery for Mexican pastries.

Dinner

Lincoln Ave Willow Glen at night (sidewalk illuminated with strings of lights) — photo by Tina Casalino

Black Sheep Brasserie: For a swanky dining experience, head over to French bistro Black Sheep Brasserie and try brussels sprouts as a side dish (and the bread pudding for dessert).
Aqui: Counter-service local chain, Aqui features organic, fresh ingredients, fused by Californian, Mexican and Southwestern influences and their infamous Industrial Swirl margaritas (where customers are restricted to two each). Tons of inside seating and a spacious back patio, the vibe here is TGIF every day.