In 2026, Westerly's biggest downtown holiday events fall on two weekends. The first is Thanksgiving weekend, when Santa arrives at Dixon Square on Friday evening, the Nutcracker Trail lists its kickoff for the same Friday, and two tree lightings follow on Saturday afternoon. The second is Sunday, December 13, when a band concert at the Armory and the Light Parade on High Street share one afternoon and evening. Between those weekends comes the Chamber's Holiday Stroll, set for a Wednesday night in downtown Westerly-Pawcatuck. It's the one most likely to catch a busy household off guard.
Here's how the season falls, with times as the organizers have posted them.
| Date | Event | Where | Time |
|---|---|---|---|
| Sat., Nov. 21 | Stonington Lobster Trap Tree lighting | Stonington, CT | 4:30 p.m. |
| Fri., Nov. 27 | Santa's Arrival | Dixon Square, 4 High St. | 6 p.m. |
| Fri., Nov. 27 | Nutcracker Trail kickoff | Listed, time TBD | TBD |
| Sat., Nov. 28 | Make Your Own Wreath | Westerly Library | 9 a.m. to noon |
| Sat., Nov. 28 | Annual Tree Lighting | Wilcox Park | 4:30 to 5 p.m. |
| Wed., Dec. 2 | 29th Holiday Stroll & Luminaria | Downtown Westerly-Pawcatuck | 5 to 9 p.m. |
| Sun., Dec. 13 | Westerly Band holiday concert | Westerly Armory | 2 p.m. |
| Sun., Dec. 13 | 7th Westerly Light Parade | High Street | 6 p.m. |
| Dec. 19 and 20 | Christmas Pops | Chorus of Westerly | Several times |
Friday Night Starts at Dixon Square
The season opens downtown the day after Thanksgiving. The Ocean Community Chamber of Commerce lists Santa's Arrival for Friday, November 27, at 6 p.m. at Dixon Square, 4 High Street. The event is free. According to the Chamber's listing, Santa heads back to the North Pole only after he has greeted every child, so the night runs as long as the line does.
The same Friday is also the listed kickoff for the second year of the Nutcracker Trail. Its 2026 page puts the kickoff at "Friday, November 27, 2026," with the time still to be announced. A paragraph lower on the same page says "Friday, November 28th," and November 28 is a Saturday this year. Check the trail's page again before Thanksgiving week. The page also says tickets will be sold the day of the event and that the auction link goes live in November.
The trail and the downtown events have the same organizer behind them. The trail's site gives 401-596-7761 as its contact number, the same number the Chamber lists for questions about the Holiday Stroll. The Westerly Sun described the 2025 trail as the region's first and said it was planned as the finale to the Chamber's centennial year. The trail's own 2025 exhibit page listed 110 hand-painted nutcrackers, each six feet tall and each sponsored by a local business, organization, school or family. Before the event, The Day put the count at 105, and a Westerly Sun photo caption said 100.
Saturday Puts Two Tree Lightings on the Same Clock
Saturday, November 28, is the fullest single day of the season.
- Morning at the library. Westerly Library & Wilcox Park lists its Make Your Own Wreath workshop from 9 a.m. to noon.
- Late afternoon in Wilcox Park. The library's Annual Tree Lighting runs from 4:30 to 5 p.m. Members of the Chorus of Westerly sing carols, the Friends of Westerly Library & Wilcox Park bring holiday treats, and Washington Trust provides hot cocoa. The event is weather permitting.
- Same start time in Watch Hill. An events calendar from Kids Out and About lists the Ocean House tree lighting for the same afternoon, 4:30 to 5:30 p.m., with Santa, fireworks, hot chocolate, cookies and an optional toy donation. That calendar notes that dates and times can change, so check with Ocean House before you go.
Both lightings start at 4:30, so a family can catch the start of one but not both. The Wilcox Park lighting is listed at 30 minutes and is the shorter of the two.
Anyone who wants a head start can try Stonington. The Chamber lists the sixth annual Stonington Lobster Trap Tree lighting for Saturday, November 21, at 4:30 p.m., and the tree stays up through January 3, 2027. That lighting comes a full week before Thanksgiving weekend.
The Wednesday That Fills the Gap
After Thanksgiving weekend, the next big downtown night comes three days into December, and it's a Wednesday. The Chamber lists the 29th Annual Holiday Stroll & Luminaria for December 2, from 5 to 9 p.m., "throughout Downtown Westerly-Pawcatuck." Luminaria line the sidewalks. Visitors get a free cup of hot chocolate and a cookie, and stores run special promotions and hand out coupons. The event runs rain or shine.
The stroll fits with the Nutcracker Trail. Last year, The Day reported, the nutcrackers stood at the United Theatre for three days and then moved out to locations around the region on December 1. The Day named Westerly, Pawcatuck, Stonington and Mystic among those locations. The Westerly Sun described the figures greeting people outside storefronts and in window displays "all season long." If 2026 follows the same pattern, walkers at the stroll will find nutcrackers in the shop windows they pass.
The trail map on the organizer's site is undated. It currently names hosts on both sides of the river, including 13th Hour Distilling, Amigos Taqueria and Bella Vita in Westerly, Bogue's Alley in Pawcatuck, and HŌMbädi Boutique at 104 Bay Street in Watch Hill. The 2026 page says sponsors and artists will be added as each nutcracker is finished, so this year's lineup is still coming together.
United Theatre fills the evenings between the stroll and the parade. Its coming-soon calendar lists:
- Jazz On A School Night Open Jam, Tuesday, December 1, 7 p.m., Knick Music Lab
- Watkins Family Hour, Friday, December 4, 8 p.m., Black Box Auditorium
- "UNITED Holiday Spectacular – We Need More Lights!", Sunday, December 6, 1:30 and 4 p.m., Black Box Auditorium
- Ana Gasteyer's Sugar & Booze Holiday Spectacular, Thursday, December 10, 8 p.m., Black Box Auditorium
December 13 Runs From the Armory to High Street
The second busy weekend is really one Sunday with two parts. The Westerly Band's "Tribute to America and the Holidays" is listed for 2 to 3:30 p.m. at the Westerly Armory. At 6 p.m., the 7th Annual Westerly Light Parade starts on High Street. The concert ends two and a half hours before the parade starts, leaving time for an early dinner downtown in between.
The parade is young by Westerly standards. The Westerly Sun reported that it began in 2019 as part of the town's 350th-anniversary celebration. It has grown into a night of floats, music and holiday displays lit with thousands of LED lights moving down High Street. The entries come from the community. The Chamber invites businesses and organizations to enter a float, a walking group or another "glowing" entry, and its 2026 application is posted on the parade's event page.
The night before the parade, United Theatre lists Rickie Lee Jones for Saturday, December 12, at 8 p.m. in the Black Box Auditorium. That makes the weekend as busy as Thanksgiving's. It also falls on the last night of the season at The Nordic in Charlestown, which lists December 12, 2026 as its closing date.
The Rain Date Lands on Christmas Pops Weekend
The Light Parade's posted rain or blizzard date is Sunday, December 20. That weekend is already booked. The Chorus of Westerly lists Christmas Pops for Saturday, December 19, at 6 p.m. and for Sunday, December 20, at 3 p.m. and 5:30 p.m. If weather pushes the parade back a week, the 5:30 Pops performance and the 6 p.m. parade start would overlap on the same Sunday evening. Anyone holding Pops tickets for that last show should check the Chamber's parade page if December 13 looks stormy.
The run continues into Monday. United Theatre lists two screenings of National Lampoon's Christmas Vacation on December 21, at noon and 7 p.m. That evening it also hosts the Roots Music Stomp at 6 p.m. in the Gallery Events Space.
At Hillary Olinger, we love the weeks when downtown Westerly fills up after dark, and we're glad to point friends and neighbors to the nights worth saving. If you're hosting family over Thanksgiving weekend and want a hand planning a Friday and Saturday around Dixon Square and Wilcox Park, let's connect.
