Newtown's holiday calendar starts on Thanksgiving morning, takes a week off, then fits most of what's left into one Saturday and Sunday. The Turkey Trot runs on Thursday, November 26. The Friends of C.H. Booth Library hold their Holiday Sale on Saturday, December 5. The next day, Newtown Youth & Family Services brings its 41st Annual Hometown Holiday Festival to Historic Main Street from 11 a.m. to 4 p.m.
For five hours that Sunday, Edmond Town Hall, Trinity Episcopal Church, the Newtown Historical Society and four decorated homes act as one venue on a shared schedule. Some of the best parts run on fixed times that end well before 4 p.m., and one of them doesn't finish until the following week.
Thanksgiving Morning Opens the Season
The Newtown Turkey Trot starts at 7:45 a.m. on Thanksgiving, Thursday, November 26, at Newtown Middle School, 11 Queen Street. It's the first fixed date on the town's late-fall calendar, and it kicks off a quiet ten days before the first weekend of December fills up.
Saturday Belongs to the Library
On Saturday, December 5, the Friends Holiday Sale at C.H. Booth Library runs from 9:30 a.m. to 5 p.m. in the library's Meeting Room. With the sale the day before the festival, Main Street gets two days of holiday traffic in a row. If you want to browse without the Sunday crowds, Saturday is your chance to get some holiday shopping done near the center of town first.
Sunday Runs on a Clock
The Hometown Holiday Festival is NYFS's largest annual fundraiser. All proceeds go to the organization's mental health, autism and community services. The festival page sells one pass for the whole day and links each part of the event to its own page with times, locations and ticket details.
The hours say 11 to 4. The timetable inside those hours is tighter:
| Time | What's happening | Where |
|---|---|---|
| 11:00 a.m. | Festival opens: market, house tours, Festival of Trees | Main Street, Edmond Town Hall Gym, Trinity Episcopal Church |
| 11:10 a.m. | First trolley departure | Edmond Town Hall front parking lot |
| 12:00 p.m. | First Nutcracker Suite performance | Edmond Town Hall Theatre |
| 12:30 p.m. | Newtown Historical Society opens to house-tour visitors | 44 Main Street |
| 2:05 p.m. | Last trolley departure | Edmond Town Hall front parking lot |
| 2:30 p.m. | Second Nutcracker Suite performance | Edmond Town Hall Theatre |
| 4:00 p.m. | Festival closes | Main Street |
| 4:15 p.m. | Festival of Trees raffle drawing | Trinity Episcopal Church, Glover Community Room |
Trolley departures leave Edmond Town Hall's front parking lot at 11:10 a.m., 11:45 a.m., 12:20 p.m., 12:55 p.m., 1:30 p.m. and 2:05 p.m. The festival pass includes one ride, and tickets are limited and handed out first come, first served. If you arrive at 2:30 for a relaxed afternoon, you've missed every trolley.
The Nutcracker Sets Everyone's Schedule
The Nutcracker Suite, presented by Newtown Centre of Classical Ballet & Voice, plays twice at Edmond Town Hall Theatre, at noon and 2:30 p.m. Each ticket admits one person to the one performance they choose. The trolley and the theater share a building, which helps with planning. A family seeing the noon show can catch the 12:55 or 1:30 trolley straight afterward. A family seeing the 2:30 show needs to have ridden the trolley by 2:05.
The Market Is the Part You Can Do Without a Pass
The holiday market runs from 11 a.m. to 4 p.m. outdoors along Main Street and indoors in the Edmond Town Hall Gym. Shopping inside is free, with food vendors, artisans and local musicians. So the gym works for a quick stop on the way to somewhere else, or for neighbors who just want a warm room and a few gifts before the season gets busy.
The Houses and the History Share a Street
The Holiday House Tours run from 11 a.m. to 4 p.m. This year's homes are on Main Street, Hanover Road and Glover Street. You can buy tickets for the house tours alone without the full festival pass. The tour is a good chance to step inside some of the town's most distinctive homes while they're decorated for the season. NYFS pitches it to people looking for decorating ideas and to people who love historic houses.
The Newtown Historical Society at 44 Main Street opens to house-tour visitors after 12:30 p.m. Its later opening suggests a natural order. Start with the houses in the late morning, stop at the Historical Society after lunch, and you've seen Main Street's homes and then the history behind them.
The Festival of Trees Outlasts the Festival
The Festival of Trees fills Trinity Episcopal Church's Glover Community Room from 11 a.m. to 4 p.m. It features decorated trees, wreaths, baskets and displays made by local businesses, organizations, families and community members, with music from "The Handbell Trio." Raffle tickets carry an additional fee, and you drop them into the box of whichever item you hope to win.
Raffle tickets are $10 for 5, $20 for 15, or $25 for 25. At the top tier you pay half as much per ticket as at the bottom tier, so a household that wants to spread tickets across several trees gets the most out of the $25 option.
The drawing is at 4:15 p.m., fifteen minutes after the festival officially closes, and NYFS encourages ticket holders to stay for it. Winners can pick up their items that evening from 5 to 6:30 p.m., or on Monday, December 7, from 10 a.m. to noon and 4 to 7 p.m., all at the Glover Community Room. Bring the raffle ticket that matches NYFS's records. Anything not collected by then moves to the NYFS office, where it's held until Saturday, December 12. Items still unclaimed after that are donated. If you win a full-size decorated tree, you'll want a car and a plan, possibly by Monday evening.
The Festival of Trees is still looking for decorators. NYFS is asking local businesses, organizations, families and community members to donate and decorate a tree, wreath, basket or display. With more than a month to go, a neighborhood group or small business could still take part.
Where the Day Ends: Sandy Hook
Main Street's schedule wraps up in the late afternoon. Sandy Hook has a new place to finish the day this year. CT Insider reported that Red Brick Tavern opened at 1 Glen Road in September 2026, co-owned by Ben Zirolli and John Gazzola. It took over the building where The Foundry Kitchen & Tavern ran from 2013 until March of this year. CT Insider's October restaurant roundup placed it in Towne Hall Hospitality's group, which also runs Cover Two Sports Café in Newtown.
According to CT Insider, the building dates to the 1850s and keeps its original woodwork and tin ceiling, with warm wood furniture, vintage-style wallpaper and a brick patio overlooking the Pootatuck River. The menu is New England tavern food: beer-battered fish and chips with a charred-jalapeño tartar sauce, clam chowder, lobster rolls, and a black-truffle mafaldine. The drinks list includes a cocktail based on the vintage champagne cocktail named for Marilyn Monroe and Arthur Miller, who lived in nearby Roxbury.
The village's own December tradition is still to come. In 2025, the Sandy Hook Organization for Prosperity held its tree lighting on the first Saturday of December, with Santa and caroling. It also ran a lamppost adoption program for the village's 79 lampposts, starting at $75, as The Newtown Bee reported last year. The Bee's same roundup covered the Ram Pasture lighting in the center of town, which raised money for bulbs and luminaria through $10 donations. Both are annual traditions, and the 2026 dates will come from the organizers and the Bee. Once they're announced, Newtown's December will have a second fixed date to plan around.
A Three-Day Plan for the First Weekend
Everything above fits into a short sequence:
- Saturday, December 5: Friends Holiday Sale at C.H. Booth Library, 9:30 a.m. to 5 p.m.
- Sunday, December 6, late morning: house tours and the indoor market, where shopping is free, then a trolley seat on the 11:45 or 12:20 if you're seeing the 2:30 Nutcracker, or the 12:55 or 1:30 if you're seeing the noon show.
- Sunday afternoon: Historical Society after 12:30, the Festival of Trees before 4, and the 4:15 drawing if you bought raffle tickets.
- Sunday evening: dinner at Red Brick Tavern on Glen Road.
- Monday, December 7: last same-week pickup window for raffle winners, 4 to 7 p.m.
The house tours are a reminder of how Newtown homes look when they've been prepared and shown at their best. If December has you wondering what your own home would bring, Elizabeth Casey can give you a clear, local answer based on more than 30 years of Fairfield County sales. Get Your Instant Home Valuation, and enjoy the festival knowing where you stand.
