Most of December on Smithtown's Main Street costs something to get in. A seat at the Smithtown Performing Arts Center's Frozen Jr. is $26.50. The Polar Express movie night is $15 for adults and $12 for children. The Smithtown Historical Society's Holiday Trail of Lights is $10 a person.
The newest event this season charges nothing. On Saturday, December 12, from noon to 4 p.m., the Greater Smithtown Chamber of Commerce holds its first Mistletoe Market on Main, a holiday street festival. It becomes the free daytime centerpiece of a December that has mostly been sold one ticket at a time. It also falls on a Saturday when the PAC, at the center of Main Street, has a 2 p.m. Frozen Jr. matinee.
What the Chamber Is Putting on Main Street
The event listing on LongIsland.com marks the market as a free event on Main Street, Smithtown, 11787. The listing describes it this way:
"Main Street in Smithtown will be transformed to a holiday street festival, including a North Pole Express train ride, Ice Sculpting, Hot Cocoa, Craft vendors, Photos with Santa, Ornament Decorating, Bounce House, cookie contest and more!"
That quote is the whole program so far, and nearly all of it is built for kids:
- North Pole Express train ride
- Ice sculpting
- Hot cocoa
- Craft vendors
- Photos with Santa
- Ornament decorating
- A bounce house
- A cookie contest
The event is set up around local business support. The Greater Smithtown Chamber of Commerce invited businesses to partner on it, with sponsorship packages starting at $250 and Main Street holiday banners offered in the same campaign. The website on the listing's contact entry goes to Freebird Festival Productions.
The Rest of December Comes With a Ticket
Main Street's ticketed season runs the length of the street. The Historical Society's grounds are at the east end, and the PAC sits close to the middle at 2 East Main Street.
| Event | Where | When | Cost |
|---|---|---|---|
| Frozen Jr. | Smithtown Performing Arts Center, 2 E. Main St. | November 21 to December 30 | $26.50 per person |
| The Polar Express Movie Night & Holiday Extravaganza | Smithtown Performing Arts Center | Thursday, December 3, 6 to 9 p.m. | $15 adults, $12 children |
| Holiday Trail of Lights 2026 | Smithtown Historical Society, 239 E. Main St. | Multiple dates | $10 per person, kids under 3 free |
| Mistletoe Market on Main | Main Street | Saturday, December 12, noon to 4 p.m. | Free |
Each ticketed event has its own audience. The Polar Express night is a fundraiser hosted by the Smithtown High School West Interact Club and the Smithtown Sunrise Rotary Club. Doors open at 6 p.m. for caroling by the Smithtown High School West Carolers, photos with Santa, holiday storytelling and raffle baskets. The film starts on the main stage at about 7 p.m., pajamas are encouraged, and all proceeds go to Smithtown Charities.
The Holiday Trail of Lights turns the Historical Society grounds into a lit path lined with trees from the Society's Tree Contest. Food and drinks come from local vendors, and the evening adds marshmallows roasted over a fire, live music, photos with Santa and shadow puppets. Parking is on the grounds at 239 East Main Street.
Frozen Jr. has the longest run of anything on the street. It is based on the 2018 Broadway musical and includes five songs written for that production. Families who need a quieter house can book the sensory performance on Friday, December 4, at 7 p.m.
So Santa appears three times on this list. At the Polar Express night and the Trail of Lights, a photo with him comes with the price of admission. At the Mistletoe Market, it comes free with a walk down Main Street.
December 12 at 2 East Main
On the PAC's Frozen Jr. schedule, December 12 has a 2 p.m. performance, two hours into the market's four. The audience for a junior production of Frozen overlaps heavily with the families a bounce house and Santa photos draw. For one afternoon, the season's biggest free event and its longest-running ticketed one share the middle of Main Street.
A family holding matinee tickets can plan the day around both:
- Arrive near noon while the market opens, and do the Santa photos and ornament decorating first, before lines build.
- Head to the theater ahead of the 2 p.m. curtain at 2 East Main Street.
- Come back out after the show for hot cocoa and the craft vendors before the market closes at 4 p.m.
Parking that Saturday will be the sticking point. The PAC's parking guidance points theatergoers to the Town lot on the north side of Main Street between Bank Street and Landing Avenue, which has 110 spaces, plus street parking on Lawrence Avenue. The same page says the People's United Bank lot and the back lot at Walgreens can be used only with permission. A market crowd and a matinee crowd will be after the same 110 spaces, so arriving early does more good on December 12 than on any other date in the run.
Families who want Frozen Jr. without the street festival have plenty of other matinees. There are 2 p.m. shows on the weekend after Thanksgiving, on December 13, 19 and 20, and again in the days after Christmas.
The Other December Traditions on Smithtown's Calendar
The Mistletoe Market joins a few December traditions that Smithtown already has, and recent years show when they tend to fall.
The Town of Smithtown has held its holiday tree lighting at Town Hall, 99 West Main Street. In 2024 it ran on December 3 from 5 to 6:30 p.m., and the Town's notice for that evening listed it as free for Smithtown residents, with Santa and local performances on the program.
The Smithtown Fire Department's Christmas parade ran on December 20 in 2025. It started at 4 p.m. from department headquarters on Elm Avenue, after cookies with Santa at 2 p.m.
Put those patterns beside this year's market and the month fills out. The tree lighting has come early in December, the parade has come in the week before Christmas, and the Mistletoe Market now takes a Saturday in between.
A Warm-Up on West Main
The west end of Main Street has a newer holiday stop too. Taste Buds Kitchen held its grand-opening ribbon cutting on August 20, 2026. Its studio at 102 West Main Street, Suite H, offers cooking classes and events for children and adults. The Smithtown studio's page lists Gingerbread House Decorating workshops with November and December availability. The studio is almost directly across from Town Hall at 99 West Main, which makes it an easy weeknight warm-up before the street festival.
From 99 West Main to 239 East Main, Smithtown's December covers the full length of its downtown. On December 12, the Chamber's market makes Main Street itself the event, and the listing marks it free.
A busy Main Street in December shows a hamlet at its best, and many sellers want a listing to look the same way. At Bona Fide Fine Homes & Estates, our in-house design and restoration team prepares Smithtown homes so they photograph and show well in winter light, and we time each launch with the season in mind. If you're thinking about a sale in early 2027, Schedule a List & Launch Consultation and we'll plan the prep work and the timing with you.
