2021 Winter Holiday Activities for the Whole Family! | Greenwich 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 Greenwich Moms has organized all the best activities in Greenwich and the surrounding areas into one, easy to follow guide!

Brought to you by our partners, Troy’s Nurseries, we are excited to present the GREENWICH MOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family!

Troy Garden Nurseries

Come share the magical experience of Christmas at Troy’s Nurseries, a family favorite for generations! Choose from a wide selection of the highest quality Fraser fir Christmas trees in all sizes. Our Troy’s team will help load your tree onto your vehicle or we can deliver and set up in your home! We specialize in customizing wreaths, containers, lighting, roping and bows with a large selection of ribbons. We are here to help you with all of your indoor/outdoor holiday decorating needs. 

Children, pets and adults are welcome to visit Santa on December 5th, 12th and 19th from 11am-2pm and take photos while sipping on complimentary hot apple cider. 
With hundreds of ornaments and themes to choose from, beautiful gifts and holiday decor in our barn gift shop, this is a must see magical holiday experience! Troy’s is the place to make holiday memories for years to come! Don’t miss out!
Our holiday hours are 8-5 Monday-Friday and 9-5 Saturday & Sunday

November 26 – January 2
Visit Santa: December 5th, 12th and 19th from 11am-2pm
Monday – Friday 8am – 5pm 
Saturday & Sunday 9am – 5pm
Troy Garden Nurseries, 97 Bedford, Banksville Rd, Bedford, NY

Junior League’s The Enchanted Forest

The Junior League of Greenwich volunteers have created a special, digitally accessible Enchanted Forest with a variety of experiences for you to enjoy with your friends and family, from the safety of your own home. JLG President, Karen Richard, explains “Greenwich residents have enjoyed this hallmark event for over 40 years. We are thrilled to continue the tradition this year by offering many of the best parts of the past, in a mix of virtual and in person experiences for adults and children.”

Choose from Gingerbread Decorating Kits, a Santa VIP Experience Drive-by at your home with Holiday Goody Bags, a Zoom Storytime session with Santa, and a Letter from Santa customized for your child. An online Auction will be on the Junior League of Greenwich website November 19-21 only, with the auction closing at 3:00 pm., Sunday, November 21. All items can be viewed at https://www.jlgreenwich.org/the-enchanted-forest/.

Celebrate Chanukah with Chabad of Greenwich

Celebrate Chanukah with Chabad of Greenwich! Join us for a night of festivities, complete with a Car Menorah Parade, Grand Menorah Lighting on Greenwich Ave and a Chanukah Concert! Fun for all ages! Parking will be available along Greenwich Ave.

December 5
Register at chabadgreenwich.org/chanukahcelebration

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

Greenwich Botanical Center Gingerbread Gnome Cookie Kits

Fun for the entire family! Happiness Is… Chef Chris takes you on another virtual cooking adventure to support Greenwich Botanical Center while teaching her world class Garden Gnomie gingerbread recipe…each Gingerbread Garden Gnomie Kit includes recipe with dough for six cookies, royal recipe with white and green icing, Guittard chocolate noses, Garden Gnomie cookie cutter donated by Greenwich Grown and a Garden Gnomie ornament donated by Sam Bridge Nurseries! Kits are to be picked up at Happiness Is…Banksville Cafe & Market on Friday, December 3, 2:00 – 5:00 p.m.

Deadline to order is November 30th at 4:00 pm
December 3, 2:00 – 5:00 p.m Pick Up

Greenwich Historical Society Winter Festival

In the spirit of Antiquarius, the Greenwich Historical Society presents a series of special festive fundraising events for the community to enjoy! December 2-4, shop the Winter Market at Christ Church Greenwich and celebrate the season at the Festival of Trees at the Historical Society. Swing by the Holiday Festival on Friday evening from 4-7pm to enjoy the family-friendly fun tours of the Bush-Holley House and a visit from Santa!

December 2 – December 4
Christ Church, Historical Society and Bush Holley House

First Light Old Greenwich

Old Greenwich Merchants Association present First Light, an annual, magical event that closes Sound Beach and invites residents to come together and stroll. Bring the family! The intention of the event is to showcase local businesses, and merchants are encouraged to invite people in to celebrate the season.

December 2
Sound Beach Avenue, Old Greenwich
More Details

Operation Santa

The Cos Cob Fire Police Patrol volunteers will again deliver holiday cheer complete with Santa and The Grinch on December 11, 12, 18, 19, and special limited deliveries on Christmas morning. Santa and The Grinch will be escorted through Greenwich to deliver your pre-wrapped holiday presents to your children. The joy on your children’s faces will warm your heart and make a lasting memory for years to come. COVID-19 safety guidelines will be in place, but have no fear, Santa and The Grinch will make sure your little ones still get a photo! To participate, please sign up on the website with your desired day and time for Santa to come by.

December 11, 12, 18, 19 and 25
Register for AM Delivery on a Chosen Date

Ice Skating at Dorothy Hamill Skating Rink

Dorothy Hamill is a Town-owned ice rink that is open from early September through mid-March. The Rink offers a variety of ice skating activities and programs for all ages.

November 26 – December 24
Dorothy Hamill Skating Rink, Sue Merz Way, Greenwich
More Details

Greenwich Moms Holiday Boutique

Shop your favorite local brands for the holidays and support Welcome Baby! 

November 30
10am – 3pm
Field Club, 276 Lake Avenue, Greenwich CT

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

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

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 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

Mistletoe Magic – Rye

The magic is back! After a two-year hiatus, the Rye Chamber of Commerce is again hosting Mistletoe Magic. This downtown holiday family fun event will take place on the Sunday after Thanksgiving. Purchase Street will become a pedestrian only plaza, filled with fun activities, crafts, games, and performers for the entire family. 


November 28, 12pm – 3pm
Purchase Street, Rye, NY
More Details

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