We’re so excited to celebrate the 2023 holiday season! With a lot of exciting family events to choose from this year, we have put together a list of options in Stamford, surrounding towns and a day trip away!
Scroll down to find events organized by category. Just find the category you’re interested in, click the plus sign to the right of the category and a list of events will drop down for you! Once you’re done, click the minus sign to minimize the list and select another one!
Be sure to check back often for updates and new additions! And click here for our 2023 list of Holiday Light Displays in our area!
Happy Holidays!
Photos with Santa
Santa at Stamford Town Center
Daily through December 24
Monday – Saturday, 10 a.m. – 9 p.m. with a break, 1 p.m. – 2 p.m. & 5 p.m. – 6 p.m.
Sunday, 11 a.m. – 7 p.m. with a break, 2 p.m. – 3 p.m.
No reservation needed!
Holiday Market & Photos with Santa at Designs by Lee
Sundays, November 26 – December 10, 11 a.m. – 3 p.m.
No reservation needed!
Reindeer Festival & Santa at Sam Bridge Nursery & Greenhouse, Greenwich
Friday, November 24 – Saturday, December 23
Monday – Friday: noon – 6 p.m.
Saturdays: 9 a.m. – 6 p.m.
No reservation needed!
Santa Sightings at Stepping Stones Museum
Friday, November 24 & Saturday, November 25, 10:30 a.m. 12:30 p.m. 3:30 p.m.
Sunday, November 26, 12:30 p.m. 3:00 p.m.
Santa at the Westchester Mall
Daily through December 24
Click here to make a reservation!
Selfies with Santa at the SoNo Collection, Bloomingdales Court
Fridays, Saturdays & Sundays, November 24 – December 24, noon – 6 p.m.
Meet Santa Claus at Stew Leonard’s
Saturdays & Sundays, November 25 – December 17
Complimentary Photos
Experiences with Santa
Santa Calls
All calls from the North Pole will be made on Tuesday, December 12 & Wednesday, December 13, 5:30 p.m. – 7:30 p.m. FREE for Stamford residents! Submit the form here by December 11 at noon.
Brunch with Santa at Pinstripes Norwalk
Saturdays & Sundays, December 2 – December 17, 10 a.m. – 3 p.m.
Make a reservation here!
Cookies & Cocoa with Santa at the Westchester
Friday, December 8, 6 p.m. – 8 p.m. Retail Level 1 near Nordstrom
Breakfast with Santa at the Maritime Aquarium
Saturday, December 16, 8 a.m.
This event is for members
Breakfast with Santa and Stew’s Costumed Characters at Stew Leonard’s Norwalk
Saturday, December 16 & Sunday, December 17, 9:30 a.m.
Register here or here!
Holiday Movies
Join us every Friday night in December at 5 p.m. in Grand Court at Stamford Town Center for beloved holiday movies presented by Stamford Moms. All are welcome!
December 1: All I Want for Christmas is You
December 8: The Grinch, photos with the Grinch before the movie at 4:30 p.m.
December 15: Scrooged and popcorn and macaroons provided by Meal JOY
December 22: Elf, photos with Elf on the Shelf before the movie at 4:15 p.m. and popcorn provided by Around the World Pediatric Dentistry
The Polar Express 4D Experience®
Showing daily through December 31
Family Holiday Movie: The Polar Express
Friday, December 8, 4 p.m. Harry Bennett Branch
Tree Lightings
Christmas Tree Lighting & Caroling at American Legion Post 12, Norwalk
Sunday, November 26, 5 p.m.
Harbor Point 13th Annual Tree Lighting
Wednesday, November 29, 5:30 p.m.
Christmas Lighting Celebration at Stew Leonard’s Norwalk
Thursday, November 30, 5 p.m. – 7 p.m.
Holiday Tree Lighting on the Green, Norwalk
Friday, December 1, 7 p.m. – 9 p.m.
Glenbrook’s 40th Annual Holiday Tree Lighting
Saturday, December 2, 6 p.m. Hope Street Park
Springdale Holiday Tree Lighting
Sunday, December 3, 4 p.m. Marilyn Trefry Park
Heights & Lights Rapelling Santa & Tree Lighting
Sunday, December 3, 5 p.m.
Walk Through Experiences
The Holiday Wish Express at Stamford Town Center
Select dates & times, Saturday, November 18 – Sunday, December 24
Use Code: stamfordmoms for 15% off tickets!
Get tickets here!
Indoor walk through display
The Holiday Stroll at Mill River Park
Select dates & times, Friday, November 24 – Sunday, December 24
Use Code: stamfordmoms for 15% off tickets!
Get tickets here!
Outdoor walk through display
Holiday Light Spectacular at Olde Mistick Village, Mystic
Saturday, November 18 – end of January
Harvest Moon’s Festival of Lights, North Salem, NY
Friday, November 17 – Sunday, December 31
Get tickets here!
Outdoor walk through display
Bronx Zoo Holiday Lights
Select dates, Friday, November 17 – Sunday, January 7
Get tickets here!
Outdoor walk through display
Glow Hartford at the Connecticut Convention Center
Saturday, November 18 – Sunday, December 23
Get Tickets here!
Indoor walk through display
Lake Compounce Holiday Lights
Select dates, Friday, November 24 – Sunday, December 31
Get tickets here!
Outdoor walk through display
A Charles Dickens’ Christmas at Lyman Orchards
Through Saturday, December 23
Get information here!
Indoor/Outdoor
Drive Through Experiences
Westchester’s Winter Wonderland Drive Thru at Kensico Dam Plaza, Valhalla, NY
Friday, November 24 – Sunday, December 31, extra early times slots Monday – Thursday, 5:30 p.m. Saturday & Sunday, 4 p.m.
Get tickets here!
Outdoor drive through display
Magic of Lights at Pratt & Whitney Stadium
Thursday, November 23 – Sunday, December 31, Monday – Thursday, 5 p.m. – 9 p.m. Friday – Sunday, 5 p.m. – 10 p.m.
Get tickets here!
Drive through display
Bethany’s Christmas Lane
Friday, December 15 & Saturday, December 16, 6 p.m. – 8 p.m. Bethany Church, 2 Scofieldtown Road, Stamford
Holiday Trains
Holiday Train Show at the NY Botanical Gardens
Friday, November 17 – Monday, January 15, 10 a.m. – 6 p.m.
Get tickets here!
Holiday Train Show Family Party, Thursday, November 30, 5 p.m. – 9 p.m.
Santa Express & Northern Lights Limited at the Railroad Museum of New England, Thomaston
Select dates, November 24 – December 23
Get tickets here!
Great Holiday Trains Show at the Wilton Historical Society
Friday, November 24 – Monday, January 15, Wednesdays – Saturdays, 10 a.m. – 4 p.m. Sundays, noon – 4 p.m. Close Christmas Eve & Christmas Day
Winterfest and the Tunnel of Lights at the CT Trolley Museum, East Windsor
Fridays – Sundays, November 24 – December 30
Get tickets here!
Holiday Model Train Display
Saturday, November 25 & December 2, 1 p.m. – 5 p.m. 7 p.m. – 9 p.m. St. John’s Episcopal Church (entrance corner of Grove & Elm Street)
Holiday on the Hill Train Show at Lasdon Park & Arboretum, Katonah
Thursdays – Sundays, Saturday, November 25 – Sunday, December 31
Get tickets here!
Santa Train at the Danbury Railway Museum
Saturdays, December 2, 9, 16, 23 & Sundays, December 3, 10, 17
Get tickets here!
Holiday Crafts
Holiday Penguin Ornament Workshop at Home Depot
Saturday, November 25, 9 a.m. – noon (while Supplies last)
Handprint Keepsake Ornaments at Recreation Star Center (Ages 1 – 3)
Tuesday, November 28 & Thursday , November 30, 11:15 a.m. – noon
Do You Want to Build a Snowman t Recreation Star Center (Ages 2 – 4)
Wednesday, November 29 & Tuesday, December 5, 11:15 a.m. – noon
Winter Wiggles at Star Recreation Center (Ages – 3 months – 15 months)
Fridays, December 1, 8 & 15
Gingerbread House Workshop at Home Depot
Saturday, December 2, 9 a.m. – noon (while supplies last)
It is Time to Decorate Your Christmas Tree at Recreation Star Center (Ages 2-4)
Wednesday, December 6 & Thursday, December 7, 11:15 a.m. – noon
All Day Ornament Painting Party at Lucky Penny Pottery
Thursday, December 7, noon – 8 p.m.
Make Your Own Holiday Ornaments at The Big Picture Art Studio
Friday, December 8, 3:45 p.m.
Saturday, December 9, 10 a.m.
Origami Hour: Holiday Season
Wednesday, December 13, 5:30 p.m.
Harry Bennett Branch
Make Your Own Gingerbread House at The Big Picture Art Studio
Friday, December 22. 1:30 p.m.
Saturday, December 23, 10 a.m.
Holiday Baking
First Annual Gingerbread Fundraiser for Salvation Army of Stamford
Make a $50 donation to Gingerbread Fundraiser at here and receive a Gingerbread Kit to decorate with loved ones! Drop off your masterpiece at Stamford Town Center to be displayed as a part of the Gingerbread Village, December 1-10!
Kids Cookie Decorating Class, Designs by Lee
Friday, November 24, 11 a.m.
Gingerbread Decorating Fundraiser
Saturday, December 2, 11 a.m. – 2 p.m. 47 Kirkham Place, Stamford
Kids Gingerbread House Decorating at Designs by Lee
Sunday, December 3 & Saturday, December 9, 11 a.m.
Toddler Workshop: Reindeer Cupcakes, Stew Leonard’s Norwalk
Tuesday, December 5 & Wednesday, December 6, 10 a.m.
Register here or here!
Adult Gingerbread House Decorating Night at Designs by Lee
Saturday, December 9, 7 p.m.
Family In Person Gingerbread Decorating, Hudson Table Stamford
Sunday, December 10, 11 a.m.
Gingerbread House Decorating (Pick Up Kit), Hudson Table Stamford
Sunday, December 10
Tiny Tot Cookie Decorating at Recreation Star Center (Ages 1-3)
Tuesday, December 12 & Wednesday , December 13, 11:15 a.m. – noon
Candy Cane Pizza Making Class for Toddlers, Stew Leonard’s Norwalk
Wednesday, December 13, 10 a.m.
Christmas Tree Cone Making Class, Stew Leonard’s Norwalk
Tuesday, December 19, 10 a.m.
Gingerbread House Decorating at Recreation Star Center (Ages 2‐4)
Tuesday, December 19 & Wednesday, December 20, 11:15 a.m. – 12:15 p.m.
Holiday Shows
A Magical Cirque Christmas at the Palace Stamford
Thursday, November 30, 7 p.m.
Get tickets here!
The Nutcracker, The Darien Arts Center
Saturday, December 2, Sunday, December 3, Friday, December 8, Saturday, December 9 & Sunday, December 10
Get tickets here!
Rudolph the Red-Nose Reindeer at the Palace Stamford
Sunday, December 3, 2 p.m. & 6 p.m.
Get tickets here!
Cirque Dreams Holidaze, Wallingford
Friday, December 8 & Saturday, December 9
Get tickets here!
Ballet School of Stamford Nutcracker Suite
Saturday, December 9, noon & 3 p.m. Stamford Town Center (FREE)
Sunday, December 10, noon & 3 p.m. Whittingham Discovery Center, purchase tickets here
Songs of the Season at the Palace Stamford
Sunday, December 10, 6 p.m.
Connecticut Ballet’s The Nutcracker at the Palace Stamford
Saturday, December 16, 2 p.m. & 6 p.m. Sunday, December 17, 1 p.m. & 5 p.m.
Get tickets here!
World Ballet Series: Nutcracker
Saturday, December 23, 6 p.m.
Get tickets here!
Holiday Markets
Stamford Moms Holiday Sip & Shop at Third Place by Half Full Brewery
Sunday, December 3, 10 a.m. – 3 p.m.
Holiday Market at the New Canaan Nature Center
Saturday, November 18, 10 a.m. – 5 p.m.
New Canaan Artisans Boutique at Roger Sherman Inn
Saturday, November 18, 10 a.m. – 2 p.m.
(Preview on Friday, November 17, 6 p.m. – 8 p.m.)
2023 Stamford High Holiday Fair at Stamford High
Saturday, November 25, 9:30 a.m. – 3:30 p.m.
Designs by Lee Holiday Market at Designs by Lee
Sundays, November 26 – December 10, 11 a.m. – 3 p.m.
Craft Fair at American Legion Post 12, Norwalk
Sunday, November 26, 10 a.m. – 3 p.m.
Holiday Sip & Shop at Abilis Gardens & Gifts, Greenwich
Wednesday, November 29, 5 p.m. – 9 p.m.
Betts Store Holiday Sip & Shop Event at the Wilton Historical Society
Thursday, November 30, 5 p.m. – 7 p.m.
Mater Salvatoris Christmas Fair
Saturday, December 2, 10 a.m. – 1 p.m. Mater Salvatoris School
Winter Market at Greenwich Social Club
Saturday, December 2, 1 p.m. – 5 p.m.
Winter Wonderland Vendor Market
Sunday, December 10, 5 p.m. – 9 p.m. Yerwood Center
Christmas Carol Sing Nativity Pageant & Holiday Market
Sunday, December 17, 3 p.m. – 7 p.m. St. John’s Episcopal Church, Stamford
Hanukkah Events
Create Your own Hanukkah Menorah at The Big Picture
Friday, December 1, 3:45 p.m. Saturday, December 2, 10 a.m.
Menorah Lighting Celebration, Stew Leonard’s Norwalk
Thursday, December 7, 5 p.m. – 7 p.m.
Chanukah Pizza & PJ’s, Chabad of Stamford
Thursday, December 7, 5 p.m.
RSVP here!
Chanukah Friday Night Live
Friday, December 8, 4 p.m.
RSVP here!
Hanukkah with Mazel Puppet Show
Saturday, 10 a.m. & 1 p.m. Sunday, 11 a.m. & 2 p.m. Stepping Stones Museum
Chanukah Menorah Car Parade
Saturday, December 9, 6 p.m.
Join a parade of cars decked out with menorahs as we drive through Stamford culminating with a Giant Menorah lighting at Latham park. Meet at Chabad of Stamford.
RSVP here!
Chanukah Wonderland and Menorah Lighting at SoNo Collection
Sunday, December 10, 12:30 p.m. – 3:30 p.m.
Chanukah Giant Menorah Lighting & Concert, Latham Park
Sunday, December 10, 4 p.m.
Holiday Festivals & Parties
The Enchanted Forest at the Bruce Museum
Friday, November 17, 7 p.m. – 10 p.m. Saturday, November 18, 10 a.m. – 4 p.m. Sunday, November 19, 10 a.m. – 3 p.m.
14th Annual Greenwich Reindeer Festival & Santa’s Workshop
Friday, November 24 – Saturday, December 23
First Light: Celebrate the Holiday Season in Old Greenwich
Saturday, December 2, 5 p.m. – 8 p.m.
Holiday Pajama Party at Recreation Star Center (Ages 1-3)
Thursday December 14 & Thursday December 21, 11:15 a.m. – noon
Holiday Party at the Mill River Park Carousel
Saturday, December 16, 3 p.m. – 6 p.m.
My Gym Stamford Holiday Party
Friday, December 22, 11:30 a.m. (infant/waddler) 4:30 p.m. – 6:30 p.m. (all ages)
Holiday Run/Walk
YMCA of Greenwich Holiday Fun Run
Sunday, December 3, 10 a.m. Tod’s Point
Jingle Bell 5K & 1 Mile Elf Run
Saturday, December 9, 9:30 a.m. Calf Pasture Beach, Norwalk
Register here!
Steps for Kids
Saturday, December 16, 8 a.m. The Stamford Family YMCA