Pleasant Hill's holiday season has two hosts, and each one keeps its own calendar. Downtown merchants and the City of Pleasant Hill light the tree on Saturday, November 21, and hold the last event on the calendar on New Year's Eve. Between those dates, most of the season takes place in the Pleasant Hill Recreation & Park District's Senior Center and Community Center. Four of the district's events fall in the six days from December 5 to December 10.
A tree lot runs in the background for nearly four weeks, staffed for a swim team. For a free evening, a ticketed concert or a Saturday breakfast with Santa, here is the season by date and host, with the deadlines that come before the events.
Saturday Night Downtown Comes First
Downtown's season opens with Light Up the Night on Saturday, November 21, a week after the Recreation & Park District's Holiday Boutique and Crafts Fair on November 14. Visit Pleasant Hill lists it from 4:30 to 7:30 p.m. downtown, with free admission and the tree lighting at 5:30 p.m. near Jack's. The listing promises holiday arts and crafts, music, dancers, caroling, a holiday train, free hot chocolate and coffee, and a visit with Santa. Performances run on both the Main Stage and the Kids' Stage from 4:30 to 7 p.m.
The finale comes after the stages close. At 7:10 p.m., Sacred Fire Dance Company performs a light-and-flame show on Crescent Drive. If you plan to leave once the tree is lit, you'll miss it.
The City of Pleasant Hill and the downtown merchants host the evening together. The Downtown Pleasant Hill events page lists it with different hours, 6 to 8 p.m. Before you set a dinner reservation around the lighting, check the City's official Light Up the Night page.
The Tree Lot Opens the Day After Thanksgiving
Six days after the downtown lighting, the season's longest-running event opens at a shopping center corner. The 42nd Annual Dolfins Tree Lot runs from November 27 through December 22, open every day from 9 a.m. to 9 p.m. It sits in the Winslow Center parking lot at 2590 Pleasant Hill Road, at the corner of Taylor and Pleasant Hill Road, and its proceeds benefit the Pleasant Hill Dolfins Swim Team.
That is 26 straight days of 12-hour shifts, starting the Friday after Thanksgiving. The lot has been part of the season for 42 years. Every other event on this calendar lasts a few hours. The tree lot is the one that's there all season, which makes it easy to fit into an ordinary errand on Taylor or Pleasant Hill Road.
Six Days in Early December, Run by the Rec District
Once the downtown lights are up, the action moves to the Recreation & Park District's buildings. Its Fall 2026/Winter 2027 Spotlight Recreation Guide packs most of its holiday programming into the first half of December. Rodgers Ranch Heritage Center adds a boutique on the same Saturday as Breakfast with Santa.
| Date | Event | Where | Cost |
|---|---|---|---|
| Sat., Dec. 5, 8:30 or 10 a.m. | Breakfast with Santa | Senior Center, Chateau Room | $12.50; $10 district residents |
| Sat., Dec. 5, 10 a.m.–4 p.m. | Rodgers Ranch Heritage Center Holiday Boutique | Rodgers Ranch Heritage Center | Not listed |
| Wed., Dec. 9, 5–8 p.m. | Winter Fest | Pleasant Hill Community Center | Free |
| Thu., Dec. 10, 7 p.m. | Clarinet Fusion Concert | Senior Center, Chateau Room | $10; $7 by Dec. 4; $5 students |
| Thu., Dec. 17, 7 p.m. | Diablo Regional Concert Band Holiday Concert | Senior Center, Chateau Room | Free; donations accepted |
The Saturday of December 5 is the busiest day on the calendar. Breakfast with Santa runs two seatings, at 8:30 and 10 a.m. The guide promises pancakes, sausage and live entertainment, and every attendee must register. The Rodgers Ranch Holiday Boutique opens at 10 a.m. the same day and stays open until 4 p.m., selling handmade gift items. Details are posted at rodgersranch.org. A family with an early seating could make both before lunch.
The two concerts in the Chateau Room bracket the middle of the month. Clarinet Fusion, which the guide calls "Pleasant Hill's very own," plays on December 10. The Diablo Regional Concert Band follows a week later. Its concert is free, and donations at the door are split between the band and the Pleasant Hill Senior Center.
Winter Fest Is the Old Winter Wonderland on a Wednesday Night
The biggest free event in the district's lineup has changed its name but kept its schedule. The Community Center at 320 Civic Drive hosted the 34th Winter Wonderland Holiday Festival on December 6, 2023, from 5 to 8 p.m. In 2024 the district listed the free event as Winter Fest, on Wednesday, December 11, from 5 to 8 p.m., at the same Community Center. The listing included Winter Express train rides, and no registration was required. The 2025 listing kept the name, the hours and the address for December 10, and its description included a Polar Express train, Santa, vendors, seasonal treats and winter crafts.
This year continues the pattern. Winter Fest falls on Wednesday, December 9, from 5 to 8 p.m. at the Pleasant Hill Community Center, with the Polar Express train, Santa, festive crafts and live performances through the evening. Three years running, the district has held it on a weeknight in the second week of December. That puts it at the end of a school and work day, between the downtown lighting and the weekend Santa morning downtown.
In 2023, the district's own event notes warned that parking was limited and that lines for Santa and the train were cut off at a 30-minute wait marker around 7:30 p.m. Those notes applied to the 2023 event. Still, they suggest arriving early in the evening rather than at the end.
Downtown Returns for Two Late-December Mornings
After the district's concerts, the season moves back to the shopping district. Downtown Pleasant Hill lists A Merry Morning with Santa on Saturday, December 19, from 11 a.m. to 1 p.m. It's set near Jack's Restaurant & Bar, where the tree was lit in November, and offers Santa photos, treats, face painting and balloon art.
That gives Pleasant Hill families two Santa mornings two weeks apart. The Recreation & Park District's breakfast on December 5 is ticketed and requires preregistration. Downtown's morning on December 19 runs as an open midday event.
Downtown's last date is Noon Year's Eve on Thursday, December 31, from 11 a.m. to 1 p.m., a daytime way to ring in the new year early. By then the Dolfins lot will have been closed for nine days, since its final day is December 22.
The Deadlines Come Before the Dates
Most of the free events need no planning beyond showing up. The district's ticketed events have their own deadlines, and two of them fall in the first four days of December.
- Breakfast with Santa: preregister online by noon on Tuesday, December 1. Every attendee must be registered for one of the two seatings.
- Clarinet Fusion: tickets cost $7 if you buy by December 4 and $10 after that. Online sales stop at 4 p.m. on the day of the show, and door sales depend on space. Student tickets are $5, and the front desk at (925) 798-8788 can help if the student discount doesn't apply in the online cart.
- Rodgers Ranch Holiday Boutique: check rodgersranch.org before December 5 for event information.
- Dolfins Tree Lot: open daily from 9 a.m. to 9 p.m., November 27 through December 22, at 2590 Pleasant Hill Road.
The Recreation & Park District published these dates in its seasonal guide, so check with the district before any event that needs a ticket or registration. For the downtown evenings, the City's Light Up the Night page is the official source.
At the Lupe Kemper Team, we live and work in these same Contra Costa neighborhoods, and the holidays are when that's easiest to see. If you're thinking about what your Pleasant Hill home might be worth heading into the new year, request a free home valuation, and we'll talk it through, maybe after you've picked up your tree at the Winslow Center.
