When and where to take photos with Santa in Connecticut in 2021

Destinations around Connecticut will soon become a little more magical as they usher in the holiday season with visits from Santa Claus. While 2020 largely featured glass-mediated visits with Santa due to COVID-19, this year, most locations are offering both socially-distanced and non-socially-distanced options for photos with Santa. For example, Stew Leonard’s locations in Danbury and Norwalk will have a vaccinated Santa who will be stationed outdoors for photos. While Santa will be unmasked, Director of Public Relations Meghan Bell told Hearst Connecticut that they can put masks on for photos depending on parents’ or guardians’ comfort level.

Malls in Connecticut have varying guidelines for visits with Santa. At the Connecticut Post Mall, Santa will be the only one sans mask, while the photography staff and any assistants will be required to wear face coverings, according to marketing director Kelly Hapken. Deeper into Fairfield County, the Danbury Mall is requiring all photography staff and Santa himself to be vaccinated, save for religious exemptions (testing will be required for vaccine-exempt employees). 

From traditional visits with Santa at shopping malls to photo ops with the North Pole native at holiday festivals, here’s when and where you can see Santa in Connecticut this year. 

Submitted photo - CCM/Essex Steam Train Santa is joined by a young fan at the Essex Steam Train.
Submitted photo - CCM/Essex Steam Train Santa is joined by a young fan at the Essex Steam Train.Journal Register Co.

Santa on the Essex Steam Train 

When: Fridays, Saturdays and Sundays Nov. 19-28, Wednesdays through Sundays Dec. 1-19, Wednesday and Thursday Dec. 22-23
Where: 1 Railroad Avenue, Essex
Guests can ride the Connecticut version of the North Pole Express in a 90-minute musical performance of “The Night Before Christmas” featuring Santa and Mrs. Claus. 

North Pole Express

Rebecca O'Callaghan and Kate Vitale, both of Greenwich, carefully place their children Brooks O'Callaghan and Sienna Vitale on Santa's lap for a holiday photo at the Greenwich Reindeer Festival & Santa's Village at Sam Bridge Nursery & Greenhouses in Greenwich, Conn. on Dec. 19, 2019. The reindeer and Santa are returning to Sam Bridge on Nov. 26.

Rebecca O'Callaghan and Kate Vitale, both of Greenwich, carefully place their children Brooks O'Callaghan and Sienna Vitale on Santa's lap for a holiday photo at the Greenwich Reindeer Festival & Santa's Village at Sam Bridge Nursery & Greenhouses in Greenwich, Conn. on Dec. 19, 2019. The reindeer and Santa are returning to Sam Bridge on Nov. 26.

Matthew Brown / Hearst Connecticut Media

Greenwich Reindeer Festival

When: Nov. 26 through Dec. 24
Where: Sam Bridge Nursery and Greenhouse, 437 North Street, Greenwich
Guests can take photos with Santa, meet his reindeer and spend some time in Santa’s workshop.

Reindeer Festival

Cromwell resident David Sizemore, an educator by trade, has been a seasonal Santa Claus for the past decade for family and school-related functions. In 2018, he became a professional Santa by working on the North Pole Express for the Essex Steam Train.

Cromwell resident David Sizemore, an educator by trade, has been a seasonal Santa Claus for the past decade for family and school-related functions. In 2018, he became a professional Santa by working on the North Pole Express for the Essex Steam Train.

Contributed photo / David Sizemore

Westbrook Holiday Parade and Tree Lighting

When: Dec. 5
Where: 21 Essex Road, Westbrook
Guests can enjoy ice carving, horse-drawn carriage and smores at a bonfire as they await Santa’s arrival in Westbrook for the town’s annual tree lighting.

Westbrook Holiday Parade

Santa and Mrs. Claus greet visitors to the opening night of the Holiday Lights Spectacular.

Santa and Mrs. Claus greet visitors to the opening night of the Holiday Lights Spectacular.

Brian A. Pounds / Hearst Connecticut Media

New Canaan Holiday Stroll

When: Dec. 4
Where: 161 Elm Street, New Canaan
The 17th annual holiday stroll will have Santa perched in front of the Houlihan Lawrence office on Elm Street for guests to take pictures. 

New Canaan Holiday Stroll

Santa's Wonderland at Bass Pro Shops in Bridgeport during the 2020 holiday season,

Santa's Wonderland at Bass Pro Shops in Bridgeport during the 2020 holiday season,

Clayton Dodwell

Norwalk Christmas Tree Lighting and Vendor Fair

When: Nov. 28
Where: American Legion Post 12, 60 County Street, Norwalk
The annual tree lighting kicks off at 5 p.m. outside the American Legion and Santa will be stop by for a visit to help usher in the holiday season.

Tree Lighting and Vendor Fair

Santa Claus previously arrives in style aboard a Fairfield Fire Department truck to greet fans on Sherman Green, where he listens to children's holiday wish lists in a program that was sponsored by the Fairfield Chamber of Commerce in a recent year. Santa Claus is returning to Fairfield at 10 a.m. where he will be until 2 p.m., all on Artists Sunday, Sunday, Nov. 28, after two years of not doing so because of the coronavirus pandemic.

Santa Claus previously arrives in style aboard a Fairfield Fire Department truck to greet fans on Sherman Green, where he listens to children's holiday wish lists in a program that was sponsored by the Fairfield Chamber of Commerce in a recent year. Santa Claus is returning to Fairfield at 10 a.m. where he will be until 2 p.m., all on Artists Sunday, Sunday, Nov. 28, after two years of not doing so because of the coronavirus pandemic.

Meg Barone / Hearst Connecticut Media

Bethel Winter Fest

When: Nov. 26
Where: P.T. Barnum Square, Bethel
Starting at 1 p.m., downtown Bethel will come alive with the spirit of the holiday season. There will be horse-drawn carriage rides, live music, hot cocoa, food and of course, a visit from Santa.

Bethel Winter Fest

Two teams of horses from Allegra Farm in East Haddam previously take people on carriage rides in downtown Faifield, during a welcome for Santa Claus that was sponsored by the Fairfield Chamber of Commerce in a recent year. Santa Claus is returning to Fairfield at 10 a.m. where he will be until 2 p.m., all on Artists Sunday, Sunday, Nov. 28, after two years of not doing so because of the coronavirus pandemic.

Two teams of horses from Allegra Farm in East Haddam previously take people on carriage rides in downtown Faifield, during a welcome for Santa Claus that was sponsored by the Fairfield Chamber of Commerce in a recent year. Santa Claus is returning to Fairfield at 10 a.m. where he will be until 2 p.m., all on Artists Sunday, Sunday, Nov. 28, after two years of not doing so because of the coronavirus pandemic.

Meg Barone / Hearst Connecticut Media

Santa’s Arrival in Fairfield

When: Nov. 28
Where: Sherman Green, Fairfield
Santa will make a stop in Fairfield from 10 a.m. to 2 p.m. Children (and kids at heart) can visit with Santa and take home a small gift. 

Santa Comes to Fairfield

New Canaan gets ready for Christmas, as the New Canaan Exchange Club sells trees at Kiwanis Park where children and pets can visit with Santa Claus.

New Canaan gets ready for Christmas, as the New Canaan Exchange Club sells trees at Kiwanis Park where children and pets can visit with Santa Claus.

Grace Duffield / Hearst Connecticut Media

Pet Photos with Santa in Litchfield

When: Dec. 4
Where: Agriventures Agway, 7 Iffland Pond Road, Litchfield
Even pets have a chance to have their photo taken and tell Santa their holiday wishes. The first 100 visitors can also receive a free holiday goody bag. 

Agriventures Pet Photos with Santa

Santa rappelled down One Landmark Square a few days early for this year’s Heights and Lights event in Downtown Stamford. YES Network, the New York Yankees’ television channel, will broadcast the annual celebration and tree lighting in lieu of the in-person event.

Santa rappelled down One Landmark Square a few days early for this year’s Heights and Lights event in Downtown Stamford. YES Network, the New York Yankees’ television channel, will broadcast the annual celebration and tree lighting in lieu of the in-person event.

Contributed photo / Downtown Special Services District

Stamford Heights & Lights: Rappelling Santa and Tree Lighting

When: Dec. 5
Where: Landmark Square and Latham Park, Stamford
Watch Santa and New York Yankees General Manager Brian Cashman rappel from 22 stories above the city. Once they land on solid ground, Santa will make his way up Bedford Street to Latham Park for the city’s tree lighting. 

Stamford Heights and Lights

Santa, Don Konen, listens to Akshaj Singh, 6, of Danbury, tell him what he wants for Christmas during the Danbury Railway Museum annual Santa Train. Visitors rode a vintage train through the rail-yard and visited Santa and Mrs Clause in their own decorated rail cars. Saturday, December 9, 2017, in Danbury, Conn.

Santa, Don Konen, listens to Akshaj Singh, 6, of Danbury, tell him what he wants for Christmas during the Danbury Railway Museum annual Santa Train. Visitors rode a vintage train through the rail-yard and visited Santa and Mrs Clause in their own decorated rail cars. Saturday, December 9, 2017, in Danbury, Conn.

H John Voorhees III / Hearst Connecticut Media

Santa Express in Thomaston

When: Nov. 26 through Dec. 23
Where: Historic Thomaston Railroad Station, 242 East Main Street, Thomaston
All season long, guests can enjoy a visit with Santa and his elves on a train ride. Each child will also receive a small toy from Santa. 

Santa Express

Santa, Mrs. Claus and costumed characters wave to customers and employees celebrate the Stew Leonard's Tree Lighting Wednesday, December 4, 2019, at the flagship store in Norwalk, Conn.

Santa, Mrs. Claus and costumed characters wave to customers and employees celebrate the Stew Leonard's Tree Lighting Wednesday, December 4, 2019, at the flagship store in Norwalk, Conn.

Erik Trautmann / Hearst Connecticut Media

Meet Santa at Stew Leonard’s in Norwalk, Danbury and Newington

When: Nov. 26 through Dec. 21
Where: Locations in Norwalk, Danbury and Newington
From Nov. 26 through Dec. 21, customers can take a free photo with Santa in the Connecticut Stew Leonards’ locations . 

Santa at Stew Leonard's

Noah Krupa, 5, of Norwalk, was excited to meet Santa Claus for the first time Friday, Nov. 25, 2016, at the Danbury Fair mall. He put in a request for a Star Wars Lego set.

Noah Krupa, 5, of Norwalk, was excited to meet Santa Claus for the first time Friday, Nov. 25, 2016, at the Danbury Fair mall. He put in a request for a Star Wars Lego set.

Carol Kaliff/Hearst Connecticut Media

Westfield Trumbull Mall

When: December
Where: 5065 Main Street, Trumbull
The Westfield Trumbull mall is hosting three different meet-and-greet opportunities with Santa this season: a sensory visit with Santa for children with autism and other special needs from Dec. 5-12, pet photos with Santa from Dec. 6-20 and a traditional photo op with Santa from Dec. 2-24.

Santa at Westfield Trumbull

A man portraying Santa Claus sits in a mall in South Portland, Maine on Thursday, Dec. 19, 2013.
A man portraying Santa Claus sits in a mall in South Portland, Maine on Thursday, Dec. 19, 2013.Robert F. Bukaty—The Associated Press

Danbury Fair Mall

When: Through Dec. 24
Where: 7 Backus Avenue, Danbury
Shoppers can take photos with Santa at the Danbury Fair Mall through Dec. 24. 

Santa at Danbury Fair Mall

Santa HQ at the Danbury Fair Mall during the 2020 holiday season.

Santa HQ at the Danbury Fair Mall during the 2020 holiday season.

Kenneth Kast

Stamford Town Center

When: Dec. 5
Where: 100 Greyrock Place, Stamford
Dogs and cats will have a chance to take a photo with Santa on Dec. 5 and get some treats from dog daycare and grooming company Dogtopia.

Santa at Stamford Town Center

Santa Claus at the Shore Line Trolley Museum in East Haven, Conn. during the 2020 holiday season.

Santa Claus at the Shore Line Trolley Museum in East Haven, Conn. during the 2020 holiday season.

Jamie Judd

The SoNo Collection in Norwalk

When: Nov. 26 through Dec. 20
Where: 100 North Water Street, Norwalk
Looking for a new Instagram post? Take a selfie with Santa at the SoNo Collection from Nov. 26 through Dec. 20.

Santa at the SoNo Collection

Santa and Mrs. Claus at Hollandia Nurseries in Bethel, Conn. during the 2020 holiday season.

Santa and Mrs. Claus at Hollandia Nurseries in Bethel, Conn. during the 2020 holiday season.

Courtesy of Hollandia

Westfarms Mall in West Hartford

When: Dec. 6
Where: 1500 New Britain Avenue, West Hartford
The entire family including pets can take a holiday photo with Santa on Dec. 6.

Santa at the Westfarms Mall