Long Island winter festivals come to Port Jefferson, Sag Harbor and Southold

No warm weather? No problem. Bundle up and brave the cold for an outdoor festival. There are three happening throughout Suffolk County for free. Here’s a rundown of where to go to experience a winter wonderland.

PORT JEFFERSON ICE FESTIVAL

Long Island’s biggest winter celebration returns to Port Jefferson as the seventh annual Ice Festival takes place Jan. 31 and Feb. 1, presented by the Port Jefferson Business Improvement District.

"This event grows every year. In 2025, the festival brought 22,000 people to the village," Port Jeff BID president James Luciano. "Everyone looks forward to it."

Ice sculptures are the main draw with 35 new ones installed each day spread throughout the village as well as three live daily carvings all created by 10-time U.S. National Ice Carving Champion Rich Daly, of Ice Memories in Mastic Beach. This year’s sculpture theme is superheroes and villains.

"This is going to be a little more of a challenge because you have to make sure that it’s a recognizable character," Daly says. "I’ll include Marvel heroes as well as video game icons like Mario and Bowser."

The live carvings take place on Mill Creek Road in the Frigate parking lot, each running 45 minutes to an hour and involving 900 pounds of ice.

"I’ll answer questions and make jokes as we go," Daly says. "The whole process of the way the ice is made, transported and how the blocks are put together gets explained as well."

Additionally, Daly has built interactive ice games such as bowling, tic-tac-toe, corn hole and mini golf along Mill Creek Road, which gets closed to traffic. Plus, there will be an ice graffiti wall on Main Street and East Broadway, where kids can use a battery-operated tool to engrave their name or a message.

Meet and greet Spider-Man at the Spice & Tea Exchange from 1 to 4 p.m. both days in Chandler Square. The Rinx, located on East Broadway in Harborfront Park, offers live ice-skating demonstrations along with a glow stick skate at 4 to 6 p.m. and 8 to 10 p.m. on Jan. 31 and 4 to 6 p.m. on Feb. 1 ($15, $12 for ages 11 and under , $7 skate rental).

Free tractor rides around the village are conducted by Gladysz Farms holding 35 people. Loading starts at Harborview Christian Church, continues north on East Main Street to Broadway then back up Main Street and loops back onto East Main Street.

"This village is booming in the summer but in the winter we get forgotten about," Luciano says. "We are trying to get people in the momentum that we are here year-round."

• WHEN | WHERE Noon to 5 p.m. Jan. 31-Feb. 1 (rain date: Feb. 14 and 15), throughout the village of Port Jefferson (Main Street, Mill Creek Road, East Main Street, Frigate parking lot)
• MORE INFO iloveportjeff.com

SAG HARBOR’S HARBORFROST

Bypass the bathing suit for a hat, gloves and scarf, then head down to Sag Harbor for the 15th annual HarborFrost, presented by the Sag Harbor Chamber of Commerce, on Feb. 7.

"This is a chance to enjoy Sag Harbor during the off season and experience the village in all its winter glory," committee chair/Chamber past president Ellen Dioguardi says. "Its charm doesn’t only exist between Memorial Day and Labor Day."

After his Port Jeff appearance, Daly comes to Sag Harbor for another round of ice sculpting on the Long Wharf. His sculptures will be set to a nautical theme.

"All the ice sculptures get placed in front of businesses that commissioned them around the village. We list the locations on our website so people can go hunt them all down," Dioguardi says. "Whoever takes the most pictures and tags us on Instagram gets entered into a contest to win a restaurant gift certificate."

Live music is offered at Kidd Squid Brewing and the Green Room at Sag Harbor Cinema. Local businesses have special deals and feature face painting, ice tattoos and hot chocolate, plus characters like Elsa from "Frozen" will be available to take selfies. Culinary treats are sold by local restaurants like Sen, K Pasa and Page Sag Harbor.

The big finale comes at 4:45 p.m. when Keith Leaf's Amazing Fire and Juggling Show  perform fire dances on Windmill Beach right before a professional fireworks display by Grucci over the harbor at 5 p.m.

Dioguardi notes, "It’s my favorite part of the day because you get to not only see flaming hoops and torches of fire set to music in the frigid cold, but the fireworks' reflection over the water is pretty spectacular."

• WHEN | WHERE 1 to 6 p.m. Feb. 7 (rain date: Feb. 8); throughout the village of Sag Harbor (Long Wharf, Main Street)
• MORE INFO sagharborchamber.com

SOUTHOLD WINTERFEST

Now in its sixth year, Southold WinterFest, run by the Economic Development Committee for the Town of Southold on Feb. 21, is scheduled to include five food trucks, 15 restaurants and more than 50 vendors. The waterside community welcomes both local residents and visitors to attend.

"Our restaurants offer free food samples while vendors sell everything from handmade crocheted items to fresh baked sourdough bread to local wine," committee chair Jennifer Del Vaglio says. "Anybody and everybody that wants to show their goods comes out and participates. It’s a way for smaller businesses to showcase themselves."

Folks can enjoy live country music at the gazebo across from the IGA on Main Road by the North Fork Dirt Band. A fun photo op is available at the same location in the 13-foot inflatable snow globe that can hold up to five people. To warm up, head inside the First Presbyterian Church and hit the free baked potato bar while catching a set of rock music from the Hoodoo Loungers.

Go back outside to see Dan Bergin of Apple Ice, from Deer Park, perform live ice carvings across from the IGA.

"I carve ice all year in the shop inside a freezer therefore I rarely get to see the sculptures all set up outside," Bergin says. "It’s a different experience being out with the public and witnessing their reaction to what I’m making. It’s nice to get direct feedback."

Uncle Tony’s Live Reptile Show puts on two performances throughout the day and an indoor obstacle course will be available for kids to tackle. The event concludes with a drawing of a free-ticketed four basket raffle filled with items and gift certificates from local stores and restaurants.

"The spirit of this event is magical," Del Vaglio says. "It’s extra special if there’s just a little flurry of snow."

• WHEN | WHERE 10 a.m.to 3 p.m. Feb. 21 (rain date: Feb. 22), in the hamlet of Southold on Main Road (Route 25)
• MORE INFO facebook.com/southold.winterfest