The gazebo in Wolcott Park shows up again and again on Sewickley's 2026 holiday calendar. Santa sits there on the night of Friday, December 4, and he's back the next morning after the parade. On each of the four Sundays after that, horse-drawn carriages leave from the same corner of the park. When the season wraps up on Saturday, January 16, 2027, the last stop is the ballot box a few blocks away at the Sewickley Public Library.
Most of the busiest events this year fall within three days, Thursday, December 3 through Saturday, December 5. The Sewickley Valley Chamber of Commerce has set up the rest of the season to last about seven weeks, beginning the day after Thanksgiving and ending well after New Year's. Light Up Night is the centerpiece, but the Chamber's calendar opens a week before it and runs well past it.
Three Days in Early December
The early-December cluster starts the night before Light Up Night. Below is how the Chamber's calendar lays out that stretch.
| Day | Event | Where | Time |
|---|---|---|---|
| Thu., Dec. 3 | The Confluence, a Watersmith Guild film and conservation evening | The Lindsay Theater | 5:30 to 10 p.m., screening at 7:30 |
| Thu., Dec. 3 | Mahjong & Mistletoe, a Child Health Association fundraiser | Allegheny Country Club | 5:45 to 9:30 p.m., $100 per person |
| Fri., Dec. 4 | Sewickley Light Up Night | Broad, Walnut and Beaver Streets and Wolcott Park | 5 to 8:30 p.m. |
| Sat., Dec. 5 | Santa Parade, sponsored by the Rotary Club of Quaker Valley | Downtown Sewickley | 10:30 a.m. to noon |
| Sat., Dec. 5 | Village Garden Club Greens & Goodies sale | St. Stephen's Henning House | 10 a.m. to 3 p.m. |
The two Thursday events are aimed at different crowds. The Watersmith Guild's evening at The Lindsay is built around a film screening and a conservation theme. The Mahjong & Mistletoe listing promises mahjong, small plates, shopping, prizes and raffles for the Child Health Association. Both start in the early evening, and only the film night takes place in the village itself.
Friday Night, Block by Block
Light Up Night covers more of the village than any other event this season. The Chamber's 2026 Light Up Night program assigns different activities to different streets, so it helps to plan the evening by location.
- Broad Street: The main stage, with KDKA's Larry Richert as emcee. Wexford School of Rock opens at 5 p.m., and Neon Bridges Band and JAGGERZ are both listed in the 6:55 p.m. slot.
- Walnut Street: The youth stage, with Tom Forrest as emcee. John Tucci performs at 4:55 p.m., and more youth sets follow until just before 8.
- Beaver Street: Horse-drawn carriage rides from 5 to 8 p.m., leaving from FNB. A public safety and first aid tent stands at Beaver and Broad.
- Beaver and Chestnut Street parking lot: The ice sculpting contest, 5 to 7 p.m.
- Green Street parking lot: More than 20 food trucks.
- Borough Hall lawn: A Kids' Zone that the program marks as new for 2026, with SweetRide, cotton candy, face painting and a Santa Hotline.
- Wolcott Park: Santa in the gazebo.
- Sewickley Public Library: Kids' activities.
- The Lindsay Theater: A warming center.
Fireworks close the night at 8 p.m.
Because the events are spread out, parking matters more than usual. The program lists free parking at Heritage Valley Hospital, Sewickley Presbyterian Church, the Sewickley Public Library, St. James Church, St. Stephen's Church and the YMCA upper lot. Portable toilets will be at Hegner Way and Division Street. The Chamber also calls Light Up Night a PRC Zero Waste Event and asks visitors to sort compostable, recyclable and landfill trash.
Saturday Morning Moves to Wolcott Park
After Friday night fills five blocks, Saturday stays closer to the park. The Santa Parade steps off downtown at 10:30 a.m. under the Rotary Club of Quaker Valley's sponsorship. Afterward, Santa returns to the Wolcott Park gazebo until 1 p.m. That makes Saturday morning the easier time to see him without the Friday crowd.
On the same morning, the Village Garden Club holds its Greens & Goodies sale at St. Stephen's Henning House from 10 a.m. to 3 p.m. The sale offers plants, floral arrangements, soups, cookies and ornaments. It also serves as the pickup point for wreaths ordered ahead, and preorders were due November 6. Anyone who missed that deadline can still shop the rest of the sale on Saturday.
Four Sundays of Carriage Rides
After the opening weekend, the calendar settles into a weekly pattern. FNB sponsors free horse-drawn carriage rides on Sundays, December 6, 13, 20 and 27, from noon to 4 p.m., leaving from Wolcott Park.
The rides take place on both Light Up Night and these Sundays, but in different spots. On Friday the carriages leave from FNB on Beaver Street in the dark, between stage sets. On Sundays they leave from Wolcott Park in the afternoon, when the village has no stage, food trucks or fireworks. The ride is the same, but the setting is much quieter. The December 27 ride lands in the week after Christmas, so there's still a holiday outing in the village once family plans are over.
Ten Days to Vote on the Windows
On Light Up Night, the village storefronts become a contest. According to the Chamber's Holidays in the Village listing, participating businesses must be brick-and-mortar shops inside the Sewickley Business District, and their windows must be decorated by December 4.
There are two awards:
- Best of Show. The Mayor of Sewickley, the Chief of the Fire Department and the Chief of Police visit every display and vote together. The winning business chooses a nonprofit to receive a $250 donation.
- People's Choice. Anyone can vote from Light Up Night through December 13 by scanning the QR code on a poster at each display. Each person gets one vote.
Since the windows are judged in person, the vote pulls people back to the storefronts for more than a week after Light Up Night. Winners will be announced on social media.
The Passport Runs Past New Year's
The Holiday Village Passport is the longest-running piece of the season. It starts Friday, November 27, the day after Thanksgiving, and ends Saturday, January 16, 2027. That's one week before the Light Up Night fireworks, and about six weeks after them.
The Chamber's rules work like bingo:
- Pick up a passport at any participating business, or download one from the Chamber's page.
- Complete the activities on the card between November 27 and January 16.
- Visit participating businesses, each of which has a special Holiday Village Passport dot to confirm the visit.
- Fill in five squares in a row, horizontally, vertically or diagonally.
- Write your name, email address and phone number clearly, then drop the passport in the branded ballot box at the Sewickley Public Library during regular library hours, by 5 p.m. on January 16.
Winners are drawn at random from eligible entries. Prizes are one $250, one $100 and one $50 gift card, each to the participating business of the winner's choice. Winners are announced on the Chamber's social media and contacted by email or phone.
Because the passport counts visits rather than purchases on one weekend, early January matters as much as December. A five-square line can be finished during the quiet weeks after the holidays, when the shops are less crowded. The library connects the whole season. It hosts kids' activities on Light Up Night and the ballot box on the final day.
The Chamber ties the shop-local push to a bigger point of pride. Its page notes that USA Today's 10Best named Sewickley No. 1 on its 2026 list of Best Small Towns in the Northeast, announced April 8, 2026.
A practical way to plan the season is to put the ballot-box deadline on the calendar right next to December 4. Light Up Night will take care of itself. Saturday, January 16, at 5 p.m. at the Sewickley Public Library is the date that's easy to forget.
Our team lives and works on the same streets where these carriages leave and these windows go up. We spend a lot of time thinking about the parts of village life that never appear on a listing sheet. If you're thinking about how a Sewickley home fits into the next chapter of your life, or you'd just like to know what it's worth in today's market, The Monica Sample Group would be glad to help. Request a Free Home Valuation, and we'll see you in the village this season.
