From Thursday, December 3, through Sunday, December 6, there's something going on in Smithtown every evening, and most of it is on or near East Main Street. Six days later, the Greater Smithtown Chamber of Commerce holds its first Mistletoe Market on Main.
So you only need two weekends on the calendar. The first one runs four nights in a row, and the second fits into one Saturday afternoon. Everything else this season fits around those dates.
Four Nights, Thursday Through Sunday
The first weekend starts on a weeknight, which is easy to miss. Here's how the four nights line up:
- Thursday, December 3, 6 to 9 p.m.: The Polar Express Movie Night & Holiday Extravaganza at the Smithtown Performing Arts Center. Holiday activities start at 6 p.m. and the movie starts at about 7. The Smithtown High School West Interact Club and the Smithtown Sunrise Rotary Club are hosting, and proceeds go to Smithtown Charities.
- Thursday, December 3, 6 to 9 p.m.: The Kings Park Chamber's annual holiday party is the same evening at Napper Tandy's, 15 E. Main St.
- Friday through Sunday, December 4 to 6: The Smithtown Historical Society's Holiday Trail of Lights on its grounds at 239 East Main Street. Each evening starts at 5:30 p.m.
- Sunday, December 6, 4 p.m.: The Christmas Tree and Menorah Lighting at Veterans Plaza in Kings Park.
The two Thursday events start at the same hour and are aimed at different crowds. The Polar Express night is for families with young kids. The Napper Tandy's party is a Chamber gathering, and it puts an East Main Street pub at the center of Thursday night.
The Trail of Lights Runs Through Three Centuries of Buildings
The Holiday Trail of Lights takes up three of the weekend's four nights, and its setting is part of the draw. The Smithtown Historical Society has been around since 1955, and its East Main Street grounds hold a set of buildings you won't find together anywhere else in town. Long Island Wave lists the Franklin O. Arthur Farm, whose farmhouse has a front section dating to the early 18th century. There's also the Epenetus Smith Tavern, a pre-Revolutionary stop on the Brooklyn to Sag Harbor stagecoach route, and the one-room Old Smithtown Library from around 1890. The Frank Brush Barn was built in 1900 by the town undertaker and moved to the grounds in 1988, and Roseneath Cottage is a restored 1918 arts and crafts bungalow that serves as the Society's headquarters.
During the Trail of Lights, those grounds become an illuminated path lined with entries from the Society's Holiday Tree Contest, plus lights and decorations. The Society's Eventbrite page also lists food and drinks from local vendors, marshmallow roasting over a fire, live music, photos with Santa, and shadow puppets.
Here's what to know before you go:
- Admission: $10 per person, and kids under 3 get in free.
- Tickets: Sold by night through Eventbrite, so pick your evening before you buy.
- Parking: On the grounds at 239 East Main Street.
- Start time: 5:30 p.m. each evening. Check the Eventbrite listing for closing time on your night.
The Society also hosts a seasonal luncheon. Its Holiday Luncheon at the Brush Barn costs $50 per person, and you need to RSVP by December 10.
Sunday Afternoon Moves to Kings Park
The Trail of Lights' last night overlaps with the Kings Park lighting, so Sunday, December 6, is the one day you'll have to choose or plan both. The Kings Park Chamber lists the Christmas Tree and Menorah Lighting for 4 p.m. at Veterans Plaza, with seasonal music by KPCSD and treats. It starts more than an hour before the trail opens on East Main Street at 5:30, so you can catch the lighting in Kings Park and still head to the Historical Society grounds afterward.
December 12 Is the Market's First Year
The second weekend is shorter, and it's all on Main Street. The Greater Smithtown Chamber of Commerce calls the Mistletoe Market on Main its inaugural holiday street festival, scheduled for Saturday, December 12, from noon to 4 p.m.
The timing sets it apart from the first weekend. The Polar Express night, the Chamber party, the trail and the Kings Park lighting all start late in the afternoon or after dark. The market runs in daylight, and since the Chamber is behind it, the business community is the host. Updates will be on the Greater Smithtown Chamber of Commerce site as the date gets closer.
Frozen Jr. Runs Through Both Weekends
The Smithtown Performing Arts Center's run of Frozen Jr. opens on Saturday, November 21, and runs through December 30, so it spans both weekends.
| Date | Time |
|---|---|
| Sat., Nov. 21 | 7 p.m. |
| Fri. to Sun., Nov. 27 to 29 | 2 p.m. |
| Fri., Dec. 4 | 7 p.m., sensory performance |
| Sat., Dec. 5 | 7 p.m. |
| Sun., Dec. 6 | 11 a.m. |
| Sat. and Sun., Dec. 12 and 13 | 2 p.m. |
| Sat. and Sun., Dec. 19 and 20 | 2 p.m. |
| Sat., Dec. 26, through Wed., Dec. 30 | 2 p.m. |
Two dates fit neatly around the bigger events. The Friday, December 4, sensory performance is the same night the Trail of Lights opens. On Saturday, December 12, the 2 p.m. matinee falls during the Mistletoe Market's hours, so you can do the market and a show on the same Main Street afternoon. The Thanksgiving weekend matinees on November 27, 28 and 29 come before everything else on this list.
Where to Eat Between Events
Everything on this list except the Kings Park lighting is in Smithtown along Main Street, so you can pick dinner by address. These spots on Main Street have been active recently:
- Napper Tandy's Irish Pub, 15 E. Main St.: Host of the Kings Park Chamber party on December 3. It's also a No Limit Pub Poker Tour venue with Thursday games.
- Smithtown Bistro & Pub, 65 E. Main St.: Takes reservations through its own site, and a Patch event listing showed live music on its bar side in August 2026.
- The Pizzeria, 88 E. Main St.: Took over the former Buona Sera space in spring 2025, according to Greater Long Island. You can order online through its website.
- Javier's Cafe, 101 E. Main St.: Offers online ordering and is open daily.
- Smoothie King, 114 E. Main St., Suite 10: New to East Main Street this fall. Patch reported it was already serving customers in early October 2026.
- Bull Smith's Tavern, 155 W. Main St.: On the West Main side, with its own events calendar.
- H2O Seafood & Sushi, 215 W. Main St.: Also on West Main, and it takes reservations through its own site.
There's also a reopening a short drive off Main Street. Big Belly Que, the barbecue spot in a West Jericho Turnpike strip mall, came back in September 2026. Patch reported that a fire in a neighboring unit had kept it closed for more than a year.
One more evening is worth knowing about. The Polar Express night on December 3 starts at 6 p.m., the same hour as the Chamber party at Napper Tandy's, so families going to the movie may want to eat early or plan a late dinner after it ends at 9.
Planning your December around Main Street? Kate Works is happy to share more about the Smithtown businesses and traditions that make this season feel like home, whether you're putting together a family night on the Trail of Lights or deciding where to eat before the Mistletoe Market.
