Presented by:
Tis the Season to have SO much fun… that’s why we put together the 2025 Stamford Moms Holiday Event Guide! It’s full of festive event and activity 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!
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
Saturdays & Sundays, December 6 – December 14, 11 a.m. – 3 p.m.
No reservation needed!
Reindeer Festival & Santa at Sam Bridge Nursery & Greenhouse, Greenwich
November 28 – December 24
Mondays – Fridays, noon – 6 p.m.
Saturdays, 9 a.m. – 6 p.m.
Christmas Eve, 9 a.m. – 3 p.m.
Closed Sundays
No reservation needed!
Selfies with Santa at the SoNo Collection, Bloomingdales Court
Friday, November 28, 11 a.m. – 5 p.m.
Saturdays & Sundays:
November 29 – December 7, noon – 5 p.m.
December 13 – December 21, 11 a.m. – 5 p.m.
Wednesday, December 24, noon – 5 p.m.
Santa at the Westchester Mall
Click here to make a reservation
Experiences with Santa
Shark Diving Santa
On most Saturdays and Sundays December 1 – 29, 10:30 a.m. & 12:30 p.m.
This experience is free with Aquarium admission.
Santa Calls
All calls from the North Pole will be made on Tuesday, December 17, 5:15 p.m. – 7:45 p.m. FREE for Stamford residents!
Submit the form here by Friday, December 12 by noon
Signature Santa Experience at The Westchester Mall
Click here to book a one-on-one experience for your family!
Members-Only Breakfast with Santa at the Maritime Aquarium
Saturday, December 6, 8 a.m. – 10 a.m.
This event is for members only
Pancake Breakfast with Santa at the Boys & Girls Club of Greenwich
Saturday, December 6, 8 a.m. – 11 a.m.
Breakfast with Santa and Stew’s Costumed Characters at Stew Leonard’s Norwalk
Saturday, December 13 & Sunday, December 14, 8:30 a.m. & 10 a.m.
Click here to register!
Santa Meet & Greet at the Stamford PAL Center
Saturday, December 13, noon – 3 p.m.
Claus, Crafts, and Carols at 314 Beer Garden
Saturday, December 13, 1 p.m. – 3 p.m.
Breakfast with Santa at The IC
Sunday, December 14, 9 a.m. – 11 a.m.
Tony’s Brunch with Santa
Sunday, December 14, 10 a.m. – 3 p.m.
Click here for a reservation!
Breakfast with Santa at Wright Tech High School
Saturday, December 20, 9 a.m. – 11:30 a.m.
Brunch with Santa
Saturday, December 20, noon – 3 p.m. Sign of the Whale
Call (475) 250-2662 for a reservation
Celebrate The Season & Skate with Santa at Wings Arena
Saturday, December 20, 4:45 p.m. – 6:45 p.m. & Tuesday, December 23, noon – 2 p.m.
Holiday Movies
Join Stamford Moms every Friday night in December, at Stamford Town Center for beloved holiday movies shown on a brand new video wall (better picture than ever)! The movie will begin at 5 p.m. Gingerbread house decorating, balloon twisting and face painting will begin at 4 p.m.
December 5, The Grinch with a special appearance from The Grinch at 4:15 p.m.
December 12, The Polar Express pajama party! (Be sure to wear your most festive pajamas)
December 19, Rudolph the Red Nose Reindeer & Frosty the Snowman with a special appearance from Rudolph at 4:15 p.m.
December 26, Lilo & Stitch with a special appearance from Stitch at 4:15 p.m.
Complimentary popcorn all nights!
Rudolph the Red-Nosed Reindeer 4D at the Maritime Aquarium
Showing daily through December 31
Click here for tickets!
Holiday Movie Countdown: The Polar Express at Mill River Park
Saturday, December 6, 6 p.m. (in the Whittingham Discovery Center or outdoors near the ice rink)
Holiday Movie Countdown: The Grinch at Mill River Park
Saturday, December 13, 6 p.m. (in the Whittingham Discovery Center or outdoors near the ice rink)
Holiday Movie Countdown: The Best Christmas Pageant Ever
Saturday, December 20, 6 p.m. (in the Whittingham Discovery Center or outdoors near the ice rink)
Tree Lightings
Harbor Point 14th Annual Tree Lighting
Wednesday, December 3, 5:30 p.m.
Heights & Lights Rapelling Santa & Tree Lighting in Stamford Downtown
Sunday, December 7, 5 p.m.
Landmark Square & Latham Park
Walk Through Experiences
The Holiday Wish Express at Stamford Town Center
Select dates & times, Saturday, November 22 – the end of December
Use Code: STAMFORDMOMS for 15% off tickets!
Get tickets here!
Indoor walk through display
Battle of the Trees at Stamford Town Center, Level 5
Sunday, November 23 – Sunday, January 4, 10 a.m. – 6 p.m. daily
Holiday Light Spectacular at Olde Mistick Village, Mystic
Friday, November 21 – Saturday, January 31
(about 1 hour 30 minute drive from Stamford)
Lumina – Magical Lights at Harvest Moon Farm & Orchard, North Salem, NY
Select dates, Friday, November 21 – Tuesday, December 30
Click here for tickets!
Outdoor walk through display
(about a 35 minute drive from Stamford)
Bronx Zoo Holiday Lights
Select dates, Friday, November 21, 2025 – Sunday, January 4, 2026
Click here for tickets!
Outdoor walk through display
(about a 40 minute drive from Stamford)
Glow Hartford at the Connecticut Convention Center
Friday, November 21 – Tuesday, December 23
Click here to get tickets!
Indoor walk through display
(about 1 hour 15 minute drive from Stamford)
Lake Compounce Holiday Lights
Select dates, Friday, November 28 – Sunday, December 28
Click here to get tickets!
Outdoor walk through display
(about 1 hour 10 minute drive from Stamford)
Drive Through Experiences
Bethany Church’s Christmas Lane
Friday, December 12 & Saturday, December 13, 6 p.m. – 8 p.m.
2 Scofieldtown Road, Stamford
FREE to attend
Westchester’s Winter Wonderland Drive Thru at Kensico Dam Plaza, Valhalla, NY
Select dates Friday, November 21 – Wednesday, December 31
Click here to get tickets!
Outdoor drive through display
(about a 30 minute drive from Stamford)
Magic of Lights at Pratt & Whitney Stadium, East Hartford, CT
Friday, November 26 – Saturday, January 3
Click here to get tickets!
Drive through display
(about a 1 hour 15 minute drive from Stamford)
Holiday Trains
Holiday Train Show at the NY Botanical Gardens
Saturday, November 15 – Sunday, January 11
Click here to get tickets!
Everett Children’s Adventure Garden Pop-Up for drop-in
(about a 45 drive from Stamford)
Santa Express & Northern Lights Limited at the Railroad Museum of New England, Thomaston
Select dates, Friday, November 28 – Tuesday, December 23
Click here to get tickets!
(about 1 hour 5 minutes from Stamford)
Great Holiday Trains Show at the Wilton Historical Society
Opening at noon, Saturday, November 29
Wednesdays – Saturdays, 10 a.m. – 4 p.m. Sundays, noon – 4 p.m.
Polar Express Day on Saturday, December 6, 2 p.m. – 3 p.m.
Winterfest and the Tunnel of Lights at the CT Trolley Museum, East Windsor, CT
Select dates, November 28 – December 30
Click here to get tickets!
(about a 1 hour 30 minute drive from Stamford)
Holidays on the Hill Train Show at Lasdon Park & Arboretum, Katonah, NY
Select dates, Saturday, November 29 – Wednesday, December 31
Click here to get tickets!
(about a 30 minute drive from Stamford)
Santa Train Ride at the Danbury Railway Museum
Beginning Saturday, November 29 and running every Saturday and Sunday through December 22
Click here to get tickets!
Holiday Crafts
Teddy Bear Ornament at Home Depot Stamford
Saturday, November 29, 9 a.m. – noon
Click here to register!
Holiday Themed – Play and Learn at Recreation Star Center, 1170 Shippan Avenue
Tuesdays, December 2 – December 16, Wednesdays, December 3 – December 17, Thursdays, December 4 – December 18 (ages 1 -3)
Click here to register!
Handprint Keepsake Ornaments at Recreation Star Center, 1170 Shippan Avenue
Tuesday, December 2 & Wednesday, December 2, 11:15 a.m. (ages 1 – 3)
Click here to register!
Do You Want to Build a Snowman at Recreation Star Center, 1170 Shippan Avenue
Thursday, December 4, 11:15 a.m. (ages 2 – 4)
Click here to register!
Holiday Cocoa Ornament at Home Depot Stamford
Saturday, December 6, 9 a.m. – noon
Click here to register!
Art And Nature Workshop For Children – Evergreen Ornaments at the Greenwich Botanical Center
Saturday, December 7, 10 a.m. – noon
Click here to register!
It Is Time to Decorate Your Christmas Tree at Recreation Star Center, 1170 Shippan Avenue
Tuesday, December 19 & Wednesday, December 10, 11:15 a.m. (ages 2 – 4)
Click here to register!
Adopt-a-Reindeer Experience at Designs by Lee
Sunday, December 21, 11 a.m. – 3 p.m.
Cookies, Gingerbread Houses & More
Join the Third Annual Salvation Army Gingerbread Contest at Stamford Town Center!
Click here to enter!
Participation Guidelines:
- Cost of gingerbread house kit and participation donation is $25.00.
- Purchase or bake your own gingerbread house, decorate it, and drop it off at Stamford Town Center starting November 10, 2025.
- Decorated gingerbread houses must arrive to the Stamford Town Center no later than Wednesday, December 17, 2025 at 5:00 p. m.
- The Gingerbread Festival Award Ceremony will be held at 5:30pm on December 21, 2025 in Grand Court at Stamford Town Center
- Those who wish to keep their gingerbread house may pick up following the conclusion of the Awards Ceremony.
Gingerbread houses will be judged in three categories: 1) First Place Overall, 2) Most Creative, and 3) People’s Choice.D
Drop off completed Gingerbread Houses at the Stamford Town Center Concierge Desk, 10 a.m. – 6 p.m.
Holiday Cookie Decorating at Recreation Star Center, 170 Shippan Avenue
Friday, December 5 & Friday, December 12, 10 a.m. – 10:45 a.m. (ages 1 – 4)
Family In-Person Gingerbread House Decorating at Hudson Table
Sunday, December 14, 11 a.m. – 12:30 p.m.
Candy Cane Pizza at Stew Leonard’s Norwalk
Tuesday, December 16, 4 p.m.
Gingerbread House Decorating at Recreation Star Center, 170 Shippan Avenue
Tuesday, December 16 & Wednesday, December 17, 11:15 a.m. (ages 2 – 4)
Click here to register!
Candy Cane Pizza at Stew Leonard’s Norwalk
Wednesday, December 17, 4 p.m.
One Tough Cookie Family Cookie Decorating at Hudson Table
Sunday, December 21, 3 p.m. – 4:30 p.m.
Storytimes
‘The Christmas Owl’ Book Signing And Native Owl Meet & Greet at the Greenwich Botanical Center
Sunday, December 7, noon
Click here to register!
Winter Sunday Fundays: “We Celebrate the Light” in the Whittingham Pavilion at Mill River Park
Sunday, December 14, 10 a.m.
Holiday Shows
Jessica Lynn’s a Very Merry Christmas at The Palace Stamford
Sunday, November 30, 7 p.m.
Cirque Dreams Holidaze at The Palace Stamford
Thursday, December 4, 7:30 p.m.
Mannheim Steamroller Christmas at The Palace Stamford
Sunday, December 7, 7 p.m.
The Nutcracker, The Darien Arts Center
Fridays, December 5 & 12, 7 p.m.
Saturdays, December 6 & 13, 3 p.m. & 6 p.m.
Sunday, December 7, noon & 3 p.m.
Click here to get tickets!
New England Academy of Dance Presents The Nutcracker Ballet at the New Canaan High School Auditorium
Friday, December 12, 7 p.m.
Saturday, December 13, 11 a.m. & 4 p.m.
Sunday, December 14, 1 p.m. Interactive Children’s Show (ACT II Only) & 4 p.m.
Click here to get tickets!
Ballet School of Stamford Nutcracker Suite at Stamford Town Center
Saturday, December 13, 3 p.m. Sunday, December 14, noon & 3 p.m.
FREE Admission!
Connecticut Ballet’s The Nutcracker at the Palace Stamford
Saturday, December 13, 2 p.m. & 6 p.m. Sunday, December 14, 1 p.m. & 5 p.m.
Click here to get tickets!
Santa’s Circus at The Palace Stamford
Sunday, December 21, 6 p.m.
World Ballet Company: The Nutcracker at The Palace Stamford
Saturday, December 27, 7 p.m.
Holiday Markets
Stamford Moms Holiday Sip & Shop at Third Place by Half Full Brewery
Sunday, December 7, 10 a.m. – 2 p.m.
Free Admission!
Holiday Market Weekend at Mill River Park
Saturday, December 6 & Sunday, December 7, 10 a.m. – 6 p.m.
Click here for a complete list of 2025 Holiday Shopping Events!
Hanukkah Events
Family Day Brunch & Loaves of Love at Chabad of Stamford
Thursday, December 25, 10:30 a.m. – 12:30 p.m.
Giant Menorah Lighting at Latham Park
Sunday, December 14, 4 p.m.
Stew Leonard’s Menorah Lighting Celebration
Monday, December 15, 5 p.m.
Community Menorah Lighting at The Stamford Government Center
Tuesday, December 16, 4:45 p.m.
Menorah Car Parade
Saturday, December 20
After Shabbos, leave from Chabad of Stamford and parade to Latham Park for a Giant Menorah lighting at 6 p.m.
Harbor Point Hanukah Party at Commons Park
Sunday, December 21, 5 p.m.
Holiday Festivals & Parties
The Enchanted Forest at the Bruce Museum
Friday, November 21 & Saturday, November 22
Click here to get tickets!
17th Annual Greenwich Reindeer Festival & Santa’s Workshop at Sam Bridge Nursery
Friday, November 28 – Christmas Eve
Holiday Party at B1C Shippan
Saturday, December 6, 9 a.m. – 12:30 p.m.
417 Shippan Avenue
Old Greenwich Merchants: First Light
Saturday, December 6, 5 p.m. – 8 p.m.
(Lights, fire truck rides & Santa)
Pajama Party at the Recreation Star Center, 1170 Shippan Avenue
Thursday, December 11 & Thursday, December 18, 11:15 a.m. (ages 1-3)
Click here to register!
Winter Wonderland 2025 at the New Canaan Nature Center
Saturday, December 13, 10 a.m. – 1 p.m.
Click here to register!
Children’s Christmas Party at Knights of Columbus
Saturday, December 13, noon – 4 p.m.
Stamford Annual Holiday Party at My Gym Stamford
Friday, December 19, 10 a.m. & 4:30 p.m.
Click here to register!
Family Holiday Party Hosted by Fight for Two at The Residence Inn
Saturday, December 20, 10 a.m.
Holiday Party with Santa at The Mill River Park Carousel
Saturday, December 20 & Sunday, December 21, 2 p.m. – 6 p.m.
Click here to register!
Christmas Party at Angel Land
Sunday, December 21, 4 p.m. – 7 p.m.
No registration required!
Holiday Run/Walk
Jingle Bell 5K & 1 Mile Elf Run at Calf Pasture Beach, Norwalk
Saturday, December 13, 9 a.m.
Click here to register!
Wreath & Centerpiece Workshops
Wreath Decorating Workshop at the Greenwich Botanical Center
Monday, December 1, 6 p.m. – 8 p.m.
Wreath Making Workshop at the Bartlett
Tuesday, December 2, 6:30 p.m.
Click here to register!
Crafted Wreath & Cocktails at Designs by Lee
Friday, December 5, 6 p.m. – 8 p.m.
Family Wreath Decorating Workshop at the Greenwich Botanical Center
Saturday, December 6, noon – 2 p.m.
Click here to register!
Holiday Floral Centerpiece With Cynthia Humphrey Of Via Amendola Botanical Designs at the Greenwich Botanical Center
Tuesday, December 23, 10 a.m. – noon
Click here to register!
Shopping
