2021 Winter Holiday Activities for the Whole Family! (FINAL) - Westport Moms

Winter and the holiday season are a wonderful time of year! But sometimes there’s so much going on, that it becomes overwhelming to plan this special time with our families! That is why WestportMoms has organized all the best activities in Westport and the surrounding areas into one, easy to follow guide!

Brought to you by our very own, Megan Rutstein (follow her at @meganrutstein_realtor), we are excited to present the WESTPORT MOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family!

Megan Rutstein, Realtor

When it comes to making a big move for your family, Megan Rutstein is dedicated to helping you find the perfect place to call home. As an added bonus, she’s a tremendous resource for lifestyle information, and all things Westport ;)!

As we enter the holiday season, inventory levels are at historic lows and prices are continuing to rise in the Fairfield County area. Now is the time to sell. Email [email protected] to set up a confidential meeting to discuss any of your real estate needs. You can also follow Megan at @meganrutstein_realtor, and reach out anytime!

Tree Farms for Cutting – or Buying – this Holiday Season

If you are looking for a Christmas tree this holiday season, there are MANY options locally for pre-cut or “cut your own” trees! Make a day of It with the family, or go when you have some time, and enjoy the beauty of Fairfield County during this time of year!

We have organized these by town, but if there are any others you love, email us anytime at [email protected], and we will add the farm to our list!


Westport Tree Lighting & Holiday Tree Tour

The Westport Downtown Association would like to invite you to be a part of our latest effort to make Downtown a beautiful and welcoming place for all – especially during the important holiday season! Each of the past few years we’ve added a new element to enhance the holiday atmosphere of the district. This year, we will be installing a dozen beautiful, colorful, and unique holiday trees throughout Downtown. Each will be decorated by professional designers and will be themed to a different local non-profit – supporting their missions during this important season of giving.

Starting Black Friday eve, you and your loved ones will be able to tour this spectacular display to get into the holiday spirit. There will be a mobile-friendly interactive map on our website!
Your donation to our GoFundMe will help us cover the cost of the trees, lights, and decorations! We thank you for your donation!

Tree Lighting – Friday, November 26th

Santa and Horse-Drawn Carriage Hay Rides

Fairview Tree Farm LLC was established as a Christmas Tree Farm and Landscape Construction business in 1989 by Shelton native, Bradley Wells.  Today, this 60-acre scenic property remains in agriculture for future generations to enjoy. Each year, customers return to harvest their own Christmas trees, visit Santa, and select their holiday wreaths, decorations, and more. 

As an all season working farm, we are committed to providing our customers with quality craftsmanship and products, while preserving the land for both wildlife and future generations to enjoy. Come on down and visit us at the farm!

Santa Tractor HayRides Every Weekend (12pm-330pm)
Horse-draw HayRides Every Weekend (12pm-4pm)
*starting November 26th, reservations required

Holiday Lights Spectacular at the Hartford Healthcare Amphitheater

DRIVE-THROUGH HOLIDAY LIGHTS SPECTACULAR presented by Hartford HealthCare St. Vincent’s Medical Center

Open 7 Days Sun-Thu 5:00p-10:00p Fri-Sat 5:00p-12a

A happy holiday experience for people of all ages-families, couples, friends, social-and work groups! Enjoy Holiday Lights Spectacular presented by Hartford HealthCare St. Vincent’s Medical Center from the comfort of your own car as you wind through the sparkling path that leads you right through the Amphitheater. At every turn, the magical route is overflowing with spectacular light displays that bring your favorite holiday themes and characters to life. Absolutely No Buses.

$35 per car (weekday)
$40 per car (week day OR weekend)

Rudolph the Red Nosed Reindeer: The Musical at the Palace

The “most famous reindeer of all” is coming to Stamford on November 27! Kick off the holiday season and enjoy a day of family fun when Rudolph the Red-Nosed Reindeer: The Musical comes to The Palace Theatre

November 27
Palace Theatre, 61 Atlantic St, Stamford
More Details

Celebrate Chanukah at the Sono Collection

Music, Crafts and Dreidels

Join the Schneerson Center on Sunday, November 28th from 11:00am to 1:30pm located in The People’s Magnificent Room on level 2 for a fun filled afternoon. Kids and their families will have some Hanukkah holiday fun decorating menorahs and stuffing dreidels, scratch art, coloring and enjoying holiday manipulatives and library corner. This is a FREE event and fun for all ages! 

Sunday, November 28th
Sono Collection – The Magnificent Room (near Nordstrom)

Westport’s Academy of Dance – The Nutcracker

Westport’s Academy of Dance presents The Nutcracker

Saturday, November 27, 2021 at 3pm
Sunday, November 28, 2021 at 2pm

Theater seating & livestream options available

*Covid policy for this event*
Masks are required for all attending

Santa’s Arrival – Fairfield

Come and see Santa!

* Santa arrives at 10am!
* Each child can visit with Santa, share holiday wishes, and receive a small gift.
* Local non-profits represented.
* Horse and Wagon Rides.
* Fairfield Theatre Company presents Home Alone at the Warehouse @ 2pm; Tickets $5
* Festive Holiday Music from DJ Scott

Darien’s Spirit of the Season Weekend

Get your holiday shopping done early by supporting Darien’s local stores and establishments. Enjoy the holiday lights decorating the street lamp posts as you stroll, shop, and dine around town!

Friday, 11/26 – Sunday, 11/28
Shop Local Stroll in Darien
Support local businesses all weekend long and get your holiday shopping done!

Sunday, 11/28
“An Old-Fashioned Holiday” at Tilley Pond Park in Darien from 2 – 4pm.
Family fun will include festive refreshments, arts and crafts, a wood-burning fire and live music from the A Cappella group, Beachside Express!

Annual Tree Lighting with Santa at Darien Sport Shop starts at 4:30pm.
Hosted by Darien Sport Shop & Darien Parks and Recreation, the event will feature a performance by Dance on the DL, hot cocoa and treats served by the Boy Scouts and more. Santa arrives at 5pm by fire engine to help light the tree.  

November 26 – November 28
Darien, CT

The Santa Story at The Downtown Cabaret (Bridgeport)

We all know who Santa Claus is, but where did he come from? This brand new Cabaret original is the heart-warming and hilarious story of a young St. Nick and his journey to become Santa Claus. The perfect blend of music, mayhem, and merriment for the whole family that is sure to have you ringing jingle bells this holiday season.

December 4th-December 30th
Saturday & Sundays weekly plus extra show Christmas week
*Rapunzel, Wizard of Oz and Beauty & The Beast coming in 2022!

Greenwich Reindeer Festival

Santa and his LIVE reindeer – Dancer, Dasher and Prancer – are returning to Greenwich for the 13th Annual Greenwich Reindeer Festival & Santa’s Workshop presented by Jenny Allen/Compass. The cherished town tradition continues for the thirteenth consecutive year at this expansive nursery where visitors can have their photo taken with Santa, meet the reindeer and also enjoy the new Santa’s Workshop, which provides more space for families while they wait in line for their photo with Santa. This all takes place just minutes from downtown Greenwich. Parking is free.

November 26 – December 24
Sam Bridge Nursery & Greenhouses, 437 North Street

Annie at Bedford Middle School

Annie is a Broadway musical based upon the popular Harold Gray comic strip Little Orphan Annie and loosely based on the 1885 poem Little Orphant Annie written by James Whitcomb Riley, with music by Charles Strouse, lyrics by Martin Charnin, and book by Thomas Meehan. The musical’s songs “Tomorrow” and “It’s the Hard Knock Life” are among its most popular musical numbers.

Proof of vaccine or proof of negative covid test within 72 hours required. All patrons must be masked when indoors.

Shows are:
December 3rd (730pm)
December 4, (2pm & 730pm)
December 5 (2pm)
Bedford Middle School – 89 North Avenue, Westport

New Canaan Holiday Stroll

The annual Holiday Stroll has become a family favorite for New Canaan residents and those of our neighboring towns and its BACK!!. Downtown New Canaan transforms into something out of a Dickens’s story book. Friday night kicks off with the arrival of Santa Claus, a lighting of the trees, carol singing, live entertainment while the stores stay open late and offer refreshments and holiday cheer. 

Visit your favorite stores & restaurants, watch a wonderful show performed by New Canaan children, see Santa and his family, have some S’mores and take a tour of all the Gingerbread houses. Saturday December 4th Santa will be back in front of Houlihan Lawrence from 10:00 am – 3:00 pm so young children can share their holiday wish list with him!
Delicious Food Available including Vermont’s Waffle Cabin.

December 3rd (530pm-9pm)
December 4th (11am-3pm)

More Details

Winter FunFest at the Westport Country Playhouse

Winter Fun for the Whole Family! We are pleased to announce the first community event conceived, organized, and run by our Playhouse Youth Council, a group of engaged local high school students. Bring the family to a day of games, story readings, and holiday cheer — fun for every generation! 100% of the net proceeds from ticket sales and pictures with Santa will go directly to Homes with Hope, a Westport-based organization dedicated to ending homelessness in Fairfield County.

Keep your tummies warm with hot drinks while you wait to have your photo taken with Santa. Fuel up on festive snacks (and candy) for the music, scavenger hunt, winter crafts and so much more! Proof of vaccination is required for attendees aged 18 and up. Masks are required for all aged 2–18. Snowdate: December 18, 11AM–2PM

December 4th
11am – 2pm
Westport Country Playhouse
More Details

Ride a Vintage Train to see Santa Claus

That portly gent from the North Pole will once again pay a visit to the Danbury Railway Museum and you can take a ride in a vintage train through the historic railyard to visit him. This is a major fund-raising event for the museum and will take place on Saturdays and Sundays, December 4-5, 11-12, and 18-19. The museum will be open each day from noon to 7PM. Reservations are necessary for this very popular event.

When guests arrive and check-in at the restored 1903 train station, kids and parents will be able to enjoy the festively decorated museum interior. This includes a Letters to Santa coloring station, operating model railroads, and many interesting exhibits and artifact displays.

After a short train ride in a restored 1953 Rail Diesel Car through historic Danbury railyard, you’ll be escorted back to the station for a meet and greet with Santa and Mrs. Claus, where the big man himself will give out the first gifts of Christmas. New this year: parents will bring a pre-wrapped present (or select one from our online menu — see Web site for details), and Old St. Nick will give your little ones their unique present!

Trains will depart at 1230pm, 2pm, 330pm, 5pm, and 630pm. The 5pm and 6pm trains will run in darkness which will be ideal for enjoying the lighted railyard.
Afterwards, you are free to enjoy a walk through the railyard with a cup of hot chocolate – don’t forget the marshmallows!
Tickets are $20 for ages 2 and up. When making your reservation, use Offer Code “DPT21” to save $2.00 per paid admission.

December 4, 11, and 18 (Saturdays)
December 5, 12, and 19 (Sundays)

Ice Skating at Westport PAL Rink at Longshore

The Westport P.A.L. Rink at Longshore is outdoors and operational from late November through early March. It is located within Longshore Club Park. Children and adults are both welcome and group rates and private party arrangements are available. Westport handpass holders receive discounted admission. Rental skates and private instruction are also available as well as group instruction. Concession by Joey’s By The Shore is available during peak hours. Always call ahead in case inclement weather forces the rink to close or change the schedule. Please call (203)226-RINK for party rental information or email [email protected]. The schedule below is a weekly ice rink schedule for non-holidays. Please call (203) 226-RINK for holiday schedule. Please visit HERE for more info!

November – Early March
Westport PAL Rink at Longshore
More Details

Danbury Ice Arena

Danbury Ice Arena is more than just an ice rink. Head to the arena to catch a Danbury Hat Tricks game, sign up for DJ Skate or Free Skate, take a stab at the NEW Axe Tricks Lounge, or stop by the arcade for a few games. 

Location: 1 Independence Way, Danbury
Phone: (203) 794-1704


Stamford’s Holiday Stroll

Holiday Stroll is a new holiday tradition located at Mill River Park in Downtown Stamford, CT. A stroll through a festive, dazzling word of larger than life holiday light displays. After strolling enjoy our Holiday Village featuring a state-of-the-art Christmas Tree, holiday music, tasty food vendors, and the Half Full winter beer garden.

November 26 – January 9
Mill River Park, Stamford, CT

“The Polar Express 4D Experience” at the Maritime Aquarium

Watch “The Polar Express 4D Experience,” a fun condensed version of the Warner Bros. film where you view the movie in 3D, and experience special sensory in-theater effects like snow, wind, the aroma of hot cocoa, and more.

Fri., Nov. 26 (the day after Thanksgiving) and will play daily through Jan. 2.
Maritime Aquarium, 10 N Water St, Norwalk, CT 06854

Lumagica Light Show at Harvest Mood & Orchard

LUMAGICA brings a maze of lights. With over 500,000 LED bulbs, it’s the biggest light park in Westchester and Putnam County. A true light experience at Harvest Moon. Guests will experience LUMAGICA as a walking tour through a magical forest full of marvelous animal structures and festive decorations, all brilliantly illuminated by over 500,000 LED lights. Harvest Moon’s orchard will be transformed into a radiant fantasy sure to delight guests of all ages!

Tickets are available every Friday, Saturday, and Sunday beginning Friday, November 26th through Sunday, December 12th. Beginning Friday, December 17th, tickets will be available every day through December 23rd. Then again, beginning December 26th through December 30th.

November 26 – December 30
Harvest Moon, 130 Hardscrabble Road, North Salem, NY 10560

Winter Wonderland Drive Through

Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza, presented by Westchester Medical Center Health Network, will return to Kensico Dam Plaza bigger and better than ever with thousands of more lights, magical holiday animations and a live Santa! Guests will be dazzled and delighted along the 1.2 miles of holiday lights with new Elf Disco, a whimsical display of jubilant children from around the world, a breathtaking Peace on Earth LED display with animated trumpets and angels, and two new thirty-foot snowflakes to light up the largest holiday Christmas tree in Westchester! And if that is not enough, there is also a bigger and better snowstorm central that the whole family can enjoy right from the warmth and safety of your own car!

November 26 – January 2
Kensico Dam Plaza, 1 Bronx River Pkwy, Valhalla, NY

NYBG Holiday Train Show

This beloved tradition returns for its 30th year with a miniature wonderland in the warmth of the Enid A. Haupt Conservatory. Marvel at model trains zipping through an enchanting display of more than 175 famous New York landmarks—imagine the Statue of Liberty, Brooklyn Bridge, Rockefeller Center, and other favorites—each delightfully re-created from natural materials such as pine cones, acorns, and seeds.

You’ll also discover a showcase of our very own New York Botanical Garden buildings such as the iconic Haupt Conservatory and—new for this year—the majestic LuEsther T. Mertz Library Building, both designated New York City landmarks.

November 20 – January 23
New York Botanical Garden, 2900 Southern Boulevard, Bronx, NY

Bronx Zoo Holiday Lights 

Join us for a family holiday festival at the Bronx Zoo. During the evenings, the park comes to life with holiday cheer as immersive light displays, custom-designed animal lanterns and animated light shows sparkle across the zoo. The outdoor celebration is complete with festive entertainment, seasonal treats and classic holiday music. The walk-through experience is a beloved tradition, enchanting and fun for all ages.

November 29 – January 9
Bronx Zoo, 2300 Southern Boulevard, Bronx, NY

Photos with Santa at the Westchester Mall

The ultimate holiday tradition is back: Photos with Santa! Reservations are necessary. 

November 12 – December 24
The Westchester, 125 Westchester Ave, White Plains, NY
More Details

Join The Westport Moms Community

Stay up-to-date with what is happening in-and-around The Westport, CT community with local events, community highlights, and exclusive deals.