On the day after Thanksgiving, with a house full of relatives, where can a six-year-old and a wine-loving uncle spend the same evening without anyone getting bored? In Saratoga the answer is a single stretch of Big Basin Way. On Friday, November 27, the Village runs three events back to back, from 3 p.m. to 9 p.m. Each one is aimed at a different crowd, and each is timed to hand off to the next.
This is a standing date on the calendar. The Saratoga Chamber of Commerce held its holiday wine stroll on Friday, November 28, 2025, which was also the day after Thanksgiving. The 2026 schedule keeps the same order. A free afternoon for kids leads into a public tree lighting, which leads into a ticketed tasting. The handoffs overlap, though, and a mixed-age group can get split up during that overlap.
Six Hours on One Block
All three events take place within a short walk of the Saratoga Chamber of Commerce office at 14460 Big Basin Way.
| Time | Event | Where | Cost |
|---|---|---|---|
| 3 to 5 p.m. | Candy Cane Village | 14460 Big Basin Way | Free |
| 5 p.m. | Wine Experience check-in opens | 14460 Big Basin Way | Ticketed |
| 5:30 to 6:30 p.m. | Annual Holiday Tree Lighting | Blaney Plaza | Public event |
| 6 to 9 p.m. | Saratoga's Holiday Wine Experience | Historic Saratoga Village | $50 advance, $60 day of |
The afternoon is built for children. The City of Saratoga's listing for Candy Cane Village promises free photos with Santa and his elves, horse-carriage rides, holiday arts-and-crafts tables for kids, and live sing-along music. The city bills it as the event "held before the Tree Lighting Ceremony." That phrasing tells you how the day is organized. Candy Cane Village is the opening leg, and it ends half an hour before the lights come on.
The Hour When Both Crowds Share the Street
Two shifts, one for families and one for adults, would be easy to plan around. The tricky part is that they overlap.
Check-in for the wine event opens at 5 p.m. at the Chamber, the same address that hosts Candy Cane Village. Thirty minutes later, the tree lighting starts at Blaney Plaza and runs until 6:30. The tasting opens at 6. Between 5 and 6:30, ticket holders picking up wristbands, families coming out of Candy Cane Village, and people arriving for the lighting are all on the same blocks.
The city's own description of the tree lighting tells visitors to come early or stay late to enjoy Village shops and restaurants. For a group with both kids and wine drinkers, that advice settles the plan. Anyone who leaves the tree lighting at 6:30 is going home or going to dinner. Anyone with a wristband is starting a tasting that is already half an hour underway.
A Plan for a Mixed-Age Group
Once the overlap is clear, the evening sorts itself out. Here is one way a household with children and wine-tasting adults can run it:
- Arrive by 3:30 p.m. Candy Cane Village runs only two hours, and the horse-carriage rides and Santa photos are the reason to come early.
- Send one adult to check in at 5. Check-in requires a valid photo ID for every attendee plus the ticket confirmation, which can be on a phone. Each guest gets a wristband, a wine glass and the brochure listing tasting locations. Getting this done while the kids finish their crafts saves a wait later.
- Regroup at Blaney Plaza by 5:30. The tree lighting is the only part of the evening that everyone in a mixed group can attend together.
- Split at 6. Tasters head into the Village. Everyone else goes to dinner or home.
- Watch the clock if buying at the door. Day-of tickets cost $60 and are sold at the Chamber's door only until 7:30 p.m.
Parking shapes the plan too. The Chamber says free parking is available throughout the Historic Saratoga Village. It also suggests a late lunch or early dinner reservation as a way to get a good spot. On a day that starts at 3 p.m. and ends at 9, a car that arrives for Candy Cane Village can usually stay through the tasting. That favors one early arrival over two separate trips.
Where to Sit Down Between Shifts
If the plan includes a meal reservation, Big Basin Way has enough restaurants to cover very different moods within a few addresses. The places below come from the Saratoga Chamber's restaurant directory. They are listings, not confirmed event participants, so call ahead for holiday-weekend hours.
- For the kids' leg: Big Basin Burger Bar at 14413 Big Basin Way, Dos Burros at 14560, and Kandoo Patisserie & Café at 14510.
- For a relaxed early dinner after the lighting: Florentine Trattoria at 14510, Bai Tong Thai Bistro at 14515, and La Fondue at 14550.
- For a reservation dinner while the tasting runs: The Plumed Horse at 14555 and Hashiri Bettei Kaiseki Aoki at 14417, Suite A.
Several of these share address blocks. Florentine Trattoria, Kandoo, Hong's Gourmet, Mandala Indian Cuisine and Masu Japanese Bistro are all listed at 14510 Big Basin Way, so a group can split up by appetite and still be steps apart.
What the Wine Ticket Covers
The ticket is where planning ahead pays off most. The Chamber lists three prices for the Holiday Wine Experience: $50 in advance, $60 on the day, and $375 for a group of eight. Processing fees and tax are extra on all three. Eight advance tickets bought one at a time come to $400, so the group rate saves $25 before fees. Buying ahead saves $10 per person compared with the door. Online sales close at noon on November 27.
Other terms to know before buying:
- The event happens rain or shine.
- Tickets are nonrefundable but can be transferred to a friend or family member.
- The Chamber says the event often sells out.
- Live music comes from Kurt & Johnny.
The 2026 listing does not publish a winery lineup. Tasting locations are printed in the brochure handed out at check-in. For a sense of the Village's year-round wine scene, the Chamber's winery directory lists Shyr Wines at 14440 Big Basin Way, Suite 10, which it describes as a speakeasy-style tasting room open Thursday through Sunday from 4:30 to 8:30 p.m., and Roudon Smith Winery at 14572 Big Basin Way. The Chamber's broader directory also lists the Big Basin Vineyards Tasting Room at 14598 Big Basin Way, Suite B; the Mindego Ridge Tasting Room, which shares 14598 with Lexington Wine Co.; and Uncorked! at 14500. Those are regular Village addresses, not a confirmed event roster. They do show how much tasting fits onto a few blocks on an ordinary weekend.
Guests Who Stay Into December
The Friday relay starts the season, and a few more dates follow for guests who stay longer or come back. Saratoga Federated Church lists a Community Carol Sing for Saturday, December 5, at 6:30 p.m. The next afternoon, Hakone Gardens holds a tea ceremony demonstration on Sunday, December 6. Garden admission is separate. Hakone's Cultural Exchange Center is also showing "UMI," an exhibit by Chris Sicat that runs through December 2026. On the following Saturday, December 12, the city has scheduled a Quarry Park clean-up from 9 a.m. to noon.
These December dates are spread across separate weekends. On November 27, the family program, the tree lighting and the tasting all happen on one block in a single evening, and the order of the evening is set by the Chamber's 5 p.m. check-in and the 5:30 tree lighting.
Visiting family often leads to a longer talk about what makes a home in Saratoga work across generations. When those conversations start, Riese Real Estate Group can bring the same block-by-block knowledge of the Village to your own plans. Schedule a free consultation whenever you're ready.
