the busy mom's guide to preschools and activities for her busy little bee

Holiday Event Guide 2018

holiday events

Let the holiday season officially begin...our 2018 Holiday Event Guide is here! Turn up the Home Alone soundtrack, grab a big mug of hot cocoa, and browse all of the fun events we have rounded up! We hope you have a magical holiday season with your kiddos. Experiencing the excitement through their innocent eyes is such a special thing-- be sure to soak up every second of it! Happy, Happy, Merry, Merry to you all! 

Jump To Events:

November 30-December 6
December 7-December 14
December 15-December 31

Click here to view our list of local Nutcracker performances & here for holiday light displays!


November 23-December 24: Reindeer Festival & Santa's Village, Sam Bridge Nursery, Greenwich, Free

Santa, live reindeer, Winter Wonderland Carousel Rides, & North Pole Polar Express Train Rides. The town tradition continues for the tenth year! From November 23 through December 22, Santa's live reindeer will be in town. This is a memorable opportunity to meet Santa and his reindeer and have your photo taken with Santa! Fees for carousel rides, train rides, and photos with Santa.

November 23: We're Back Party, Sam Bridge Nursery, Greenwich, Free

Kick off the 10th Annual Greenwich Reindeer Festival & Santa's Village! Santa arrives at 12 noon to officially open Santa's Workshop and Photos with Santa begin! The Reindeer arrive in the afternoon. Refreshments, face painting, and balloon artists for kids. 12pm-6pm.

November 24: A Charlie Brown Christmas, The Palace Theatre, Stamford

A Charlie Brown Christmas, the Emmy® and Peabody award-winning story by Charles M. Schulz, has warmed the hearts of millions of fans since it first aired on television over fifty years ago. Now the classic animated television special comes to life in this faithful stage adaptation featuring all of your favorite characters and classic Vince Guaraldi score. Join, Charlie Brown, Snoopy, Lucy, Linus and the rest of the Peanuts gang as they mount a play, save a tree and uncover the true meaning of Christmas. 1pm & 4pm.

November 24: Model Railroad Club Open House, St. John’s Episcopal Church, Stamford

The 79-year-old club’s 150’ x 50’ 0-Scale operating model train layout is one of the largest on the East Coast. Highly detailed passenger and freight trains run through equally
detailed city and countryside; as always the colorful Circus and Holiday trains are crowd favorites! The train exhibit is located in the basement of the church. 1pm-5pm & 7pm-9pm. Adults: $5, Children: $4, Under 5: Free.

November 25: Winter Wonderland, Chelsea Piers, Stamford

A day of fun holiday activities and shopping for the entire family to benefit the Chelsea Piers Scholarship Fund! Enjoy movies, bounce house, craft making, skating and photos with Santa and performances. Get a jump on your holiday shopping and support local businesses at our pop-up shop! Members + Guests: $15; Non-Member: $25. 10am-4pm.

November 25: Christmas Tree Lighting, Darien Sport Shop, Free

Darien Sport Shop’s 40th Annual Tree Lighting Extravaganza! Please join us for this annual Christmas season opener on the Sunday after Thanksgiving. Christmas carolers, hot cocoa, donuts, coffee and Santa! 4:30pm-6pm.

November 25: Light Up Rowayton, Pinkney Park, Free

Downtown Rowayton will come alive with twinkling lights at the annual holiday town lighting. Festivities begin at Pinkney Park with caroling led by Brien McMahon’s award-winning Holiday Chamber Choir at 5:00pm and the lighting of the Christmas trees at dusk. 4:30pm-7pm.

November 27: Tree Lighting, Stew Leonard's, Norwalk, Free

Stew Leonard’s Norwalk store is kicking off the 2018 holiday season with its annual Christmas Tree Lighting celebration. The festivities begin at 5:30 p.m., with plenty of musical entertainment and more to get the crowd into the spirit of the season! Santa will spend the evening mingling with the children and handing out candy canes. Complimentary hot cocoa and cookies will be served. 5:30pm-7pm.

November 27: Tree Lighting, Harbor Point, Stamford, Free

Harbor Point 7th Annual Tree Lighting! An evening of fun and caroling by the Waterside School Choir Singers. Hot chocolate, cookies, goodie bags for the kids! 6pm-7:30pm.

November 29: Christmas Tree Lighting, Westport Historical Society, Free

After Town Hall lights the holiday tree on the front lawn pop across the street to Westport Historical Society for an evening of holiday cheer! Warm up from the cold with a cup of hot cocoa donated by our friends at Starbucks. Explore our holiday exhibits, shop for festive finds and take a quick photo with Santa! This is a free event, please join us before or after the tree lighting! 5pm-7:pm.

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November 30 & December 1: Holiday Stroll, Downtown New Canaan, Free

The annual Holiday Stroll has become a family favorite for New Canaan residents and those of our neighboring towns. 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. Saturday includes pictures with Santa at Santa’s workshop, characters roaming the streets, more live entertainment, a Gingerbread House Tour and much more.

December 1 & 2: Holiday Stroll, Greenwich, Byram, Cos Cob, Riverside, Free

Enjoy fun festivities for the whole family both Saturday and Sunday throughout downtown Greenwich, Byram, Cos Cob and Riverside. Please check the map for exact locations. Over 140 participating merchants offering holiday promotions and refreshments. Live Nativity featuring a camel and eight other animals and Greenwich area churches, two different horse drawn carriage rides, live music entertainment featuring holiday singing performance, professional ice sculpture demonstration, The Food Truck Village and letter writing to Santa and Santa's Mailboxes in many participating stores and restaurants.

December 1: Nutcracker Festival, Christ & Holy Trinity Church, Westport, Free

Tea parties, Santa, entertainment, sweets, shopping, frosty, hot cocoa, performances, free activities & fun! 9am-5pm.

December 1: Holiday Fun Fair, YWCA, Greenwich, Free

Arts & crafts, bouncy castle, holiday shopping, hot chocolate & cookies, face painting, meet & greet with Santa & his elves! 12pm-3pm.

December 1: Model Railroad Club Open House, St. John’s Episcopal Church, Stamford

The 79-year-old club’s 150’ x 50’ 0-Scale operating model train layout is one of the largest on the East Coast. Highly detailed passenger and freight trains run through equally detailed city and countryside; as always the colorful Circus and Holiday trains are crowd favorites! The train exhibit is located in the basement of the church. Adults: $5, Children: $4, Under 5: Free. 1pm-5pm & 7pm-9pm.

December 1: Gingerbread You, Gingerbread Me, Westport Library, Free

Make a life-size gingerbread you and then decorate yourself. Bring your grownup! 2pm-4pm.

December 1: Winter's Eve Festival, Cos Cob Library, Greenwich, Free

The Friends and Staff of Cos Cob Library invite you to our Annual Holiday Card Making Workshop. We provide all the supplies. You drop in and create your own unique cards for friends, family and other loved ones. See you during the festivities! 3pm-5pm.

December 1: Hanukkah Craft & Story, Norwalk Library, Free

Oh Hanukkah, Oh Hanukkah, lets light the menorah and have some holiday fun! Just in time for the holiday, children of all ages are invited to enjoy Hanukkah by making a craft and learning about the story of Hanukkah. 4pm-5pm.

December 1: Holiday Magic, Grove St. Plaza, Darien, Free

Come feel the magic of the holiday as Santa arrives on rooftop and comes down the chimney at Grove St. Plaza! While you wait for his arrival, children of any age can ride the "animals", sip some hot cocoa, and listen to the DHS Tudor Singers sing holiday carols. This is truly a special local Darien event for families of all ages! 4pm-6pm.

December 1: First Light, Downtown Old Greenwich, Free

There will be horse-drawn carriage rides, carolers, Santa at the Firehouse, St. Saviour’s Dance Group, and treats at several of the locations throughout the Village. 5pm-8pm.

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December 2: Holiday Shopping Bazaar, Stamford Museum & Nature Center, Free

Join us in the Bendel Mansion for some holiday fun. Enjoy winter treats and support your local Museum & Nature Center! Choose from a selection of: Unique and local items from our Gift Shop and our favorite Farm Market Vendors Gift Baskets Gift Memberships, and much more Children's crafts and surprise musical appearances will make your shopping experience all the more memorable. 11am-3pm.

December 2: Holiday Boutique, Sacred Heart Greenwich, Free

This festive shopping event (which is open to the public!) hosts a long list of local vendors but offers a ton more than just shopping for mom & dad. Kids will have the chance to secretly shop for their parents with pocket change at the super cute “Secret Santa Shop”; plus there will be a gingerbread workshop, photos with Santa, & more! 12pm-4pm.

December 2: Santa Run, Downtown Rowayton, Free

Santa will be making his annual visit to Rowayton aboard his big red fire engine sleigh on Sunday, December 2nd. He will arrive at the Rowayton train station at 1:00pm and then make his rounds through Rowayton, stopping at the corner of Crest and Ridgewood, Rowayton Library (where you can enjoy a sing-a-long ahead of his arrival), the Bell Island gatehouse, South Beach, the Beach Association boat house and Brendan’s 101. Children can also visit him at the Firehouse on Rowayton Avenue from 2:15-2:45pm.

December 2: Springdale Holiday Stroll, Stamford, Free

3rd Annual Springdale Holiday Stroll- Take a stroll Hope Street and meet our merchants. Take advantage of some samples or other special offers from some of the merchants. Shop, Dine and Save. Join the Springdale Neighborhood Association for one of our favorite events of the year – the Annual Springdale Tree Lighting! This event is free and all are welcome to join us for special performances, free gifts for all children in attendance, a food drive…and maybe even a surprise guest. 3pm-7pm.

December 2: Heights & Lights: Rappelling Santa & Tree Lighting, Landmark Square, Stamford, Free

From 22 stories high above Stamford Downtown, watch and cheer for Santa Claus, Rudolph, Grinch and friends as they make their daredevil descent, twisting and flying from the top of one of Stamford’s tallest buildings, Landmark Square. Then follow Santa and friends up Bedford Street to Latham Park for an evening of holiday music and join in the countdown of the annual lighting of Stamford’s Holiday Tree. 5pm-7pm.

December 3: Hanukkah Storytime, New Canaan LibraryFree

Join the United Jewish Federation as they present the PJ Library Hanukkah program to celebrate the start of the holiday with stories, crafts & treats! 10am-11am.

December 3: Menorah Lighting, Stew Leonard's, Norwalk, Free

Stew Leonard’s Norwalk store is celebrating Chanukah, the Festival of Lights, with its 27th annual menorah lighting celebration. The celebration starts with Rabbi Yehoshua Hecht of Beth Israel of Westport/Norwalk lighting an 18-foot menorah. Following the menorah lighting is a celebration complete with live music, holiday song and dance and complimentary Kosher refreshments and juice. Traditional dreidels and chocolate gelt will be distributed to all. 5pm-6pm.

December 6: Hanukkah Crafts, Darien Library, Free

Celebrate the holiday of Hanukkah in the Children's Library with this special craft! 4pm-4:30pm.

December 6: Kwanzaa: A Family Affair, Ferguson Library-South End Branch, Stamford, Free

Get ready to celebrate this special holiday with story, song, crafts and treats. 4pm-5pm.

December 6: Holiday Bedtime Story & Craft, Cos Cob Library, Greenwich, Free

Come in PJs if you wish and join Miss Judy for some fun stories. Then make a Holiday craft with Miss Lyn. 6pm-7pm.

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December 7: Visit with Santa, Darien Historical Society, Free

Santa will sit by the colonial hearth and children will tell him their special Christmas wishes. Parents - take unique photos to treasure! Free, but donations gratefully accepted. 2pm-4pm.

December 7: Gingerbread Cookie Decorating & Craft, Norwalk Library, Free

Drop in to decorate a cookie and make a craft. 3pm-5pm.

December 7: Tree Lighting, Wakeman Town Farm, Westport, Free

The farm committee brings in student singers and musicians from our local elementary schools to provide festive holiday music. This year, Broadway actress Susan Terry will sing a few holiday tunes and lead a festive sing-a-long. Volunteers pour hot cocoa and serve cookies and stoke up the bonfire for s'mores. As the sun goes down, the team lights the Tree, a tradition for three generations of the Wakeman family. 4:30pm-5:30pm

December 8: Hawaiian Holiday Breakfast with Santa, Greenwich Botanical Center

Shake off the cold and step into a tropical treat for the whole family. Enjoy crafts, music, and yummy refreshments with a Hawaiian flair. Even Santa will be riding a wave in to greet you! $10 per person (under 3 is free). 9am-11:30am.

December 8: Screening of "Elf", Avon Theatre, Stamford, Free

Special holiday screening of "Elf" which is free to the public! The Avon Theatre will be collecting canned and non-perishable food items to benefit the Food Bank of Lower Fairfield County. 11am.

December 8: Gingerbread Decorating Workshop, Westport Historical Society

Bring the whole family to decorate gingerbread for the holiday season. Add icing to gingerbread people, snowflakes, and penguins! $8-$15 (children 5 and under are free). 11am-12pm.

December 8: Santa's Spectacular Arrival by Helicopter, Waveny Park, New Canaan, Free

Santa will arrive at 11:45am to Waveny Park. Santa will then be picked up by a fire truck and brought to Weed & Duryea and Gregg’s Garden Center to greet all the kids, Selfie Pics with Santa!. Free hot dogs, hot chocolate, cotton candy, popcorn and treats for all! 11:30am-1:30pm.

December 8: Jingle Jam & Holiday Cookies, Junior Art & Music, Norwalk

Jingle Jam includes holiday art, a doodle Bar, live music & java ($12/person or $45/family, 10am-11:30am)! Or attend a cookie workshop with 6 big, sugary canvases to ice & decorate. Festive, fun & oh so yum ($45, 1pm-2pm & 4pm-5pm)!

December 9: Nativity Pageant, Pinkney Park, Rowayton, Free

Featuring local performers, clergy and live animals, this family event is a wonderful way to rediscover the joy of Christmas with your neighbors and friends. 6pm.

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December 12: Holiday Crafter-noon, Darien Historical Society

Decorate a wreath and an ornament during an afternoon event! Ages 5 and up. $15. 3pm-5pm.

December 12: Holiday Tea, Greenwich Botanical Center

An elegant multi-generational holiday tea party featuring decadent delicacies, silent auction, nature-based children's activities and tons of holiday spirit! $25-$60. 3:30pm-6pm.

December 12: Visit with Mrs. Claus, Norwalk Library, Free

Sing holiday songs, listen to a tale with storyboards, and have your picture taken with Mrs. Claus! 4pm-5pm

December 13: Holiday Stroll, Downtown Westport, Free

The Westport Downtown Merchants Association will host a festive evening that invites all to come shop local and get into the holiday spirit. Stores on Main Street and all around downtown will keep their doors open until 7pm, welcoming shoppers with warm hospitality and seasonal ambience that is sure to melt even the grinches heart! Enjoy strolling music around the town, complimentary hot cocoa served by Rye Ridge Deli, our favorite DMA elf handing out candy canes and of course, Santa will be visiting our stores throughout the evening delighting children and adults alike. Restaurants will offer featured holiday items just for our stroll night, so don’t miss out! 4pm-7pm

December 14: Holiday Party with Santa, Darien Community Association 

Join us for some holiday cheer, and to take the classic photos you enjoy every year! The highlight of the party will be your little one’s visit with Santa, set against the backdrop of a full-size Christmas tree nestled within our historic home. When there’s a line, adults will find plenty of chairs, and toddlers will have some little things to keep them occupied, including holiday cookies and juice. $10. 10am-11am.

December 14: Pizza with Santa, YMCA of Westport/Weston Gymnastics Center, Norwalk

Celebrate the holidays the Family YMCA way! Cookie decorating, craft, pizza, drink, and lots of free play in the gym! Bring your wish lists and sit on Santa’s lap. $5. 5:15pm-7pm.

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December 15: Jingle Bell Rock: Family Day with Santa, Westport Historical Society

We’re gonna rock around the museum! Bring the whole family to discover exhibits exploring the diverse holiday traditions Westporters celebrate. Take part in a variety of crafts and activities and sit for a silhouette as a holiday gift. Finally, get a selfie with Santa! $8-$15 (5 & under are free). 10am-4pm.

December 15: Holiday Storycraft, Ferguson Library, Stamford, Free

'Tis the season for stories to put you in a holiday mood, and we'll finish by making a jingle bell necklace you can wear throughout the season or give to someone special. 11am-12pm.

December 15: Winter Wonderland, New Canaan Nature Center

Come and be transported into a whole new world as the New Canaan Nature Center transforms into a Winter Wonderland filled with fun and exciting winter holiday activities for the entire family. Activities include: visits with Santa, model trains, a campfire with marshmallow roasting, caroling, crafts, reindeer games, horse-drawn wagon rides, & much more! 11am-2pm.

December 15: Horse & Wagon Rides, Downtown Westport, Free

The pick up location will be at the Historical Society at 25 Avery Place, directly across from Town Hall. The Historical Society will also host a family day with Santa that will include photos with Santa, holiday crafts, and a silhouette artist. 12pm-4pm.

December 15 & 16: Skate with Santa, Twin Rinks, Stamford

Skate with Santa this holiday season! A holiday tradition for many families. Giveaways, contests & much more! 12:30pm-2pm.

December 15: Winter Extravaganza, YMCA of Westport/Weston

Create your very own edible gingerbread house to take home and eat! Make an ornament or two! Play dreidel and reindeer games. Get into the holiday groove. Dance, sing, and move. $8/child pre-registered or $10/child at door; $20 for 3 children. 2pm-4pm.

December 15: An Old Fashioned Holiday, Tilley Pond, Darien, Free

Holiday goodies, hot cider, caroling, festive decorations, wood burning fire, kids’ ornament & cookie decorating. 4pm-6pm.

December 16: Kid's Holiday Terrarium, Terrain, Westport

Bring along the little ones to plant a holiday terrarium with living plants just in time for the holidays. $25. 10am-11am.

December 16: Storytime at the Homestead, Mather Homestead, Darien

Join us for storytelling! We'll read Twas the Night Before Christmas, have a holiday snack and make an ornament for the tree! Recommended for ages 4 to 10. $20. 2:3opm-4:30pm.

December 16: Candlelight: A Festive Family Event, Greenwich Historical Society, Free

Bush-Holley House tours are roughly 45 minutes long and cover Christmas traditions as they would have been celebrated by the Bush and Holley families. In the Vanderbilt Education Center there will also be live music, refreshments, winter themed crafts and an appearance by Santa Claus from 5pm-7pm. Doors open at 4:30pm.

December 18: Charlie Brown Christmas, Wee Burn Country Club, Darien

Join us for live performances of the beloved Charlie Brown Christmas TV special! Charlie Brown, Snoopy, Linus and friends will share the true meaning of the season with your little ones. All proceeds will benefit Person-to-Person. $25-$35 (under 2 is free). 12pm & 4pm.

December 19: Ornament Decorating, Darien Nature Center

Spend the afternoon creatively! Using natural materials we will create and decorate a variety of festive ornaments for the holidays. Space is limited and we cannot accommodate walk-ins, so please register to reserve your space! $15. 2:30pm-3:30pm.

December 19: Gifts for Giving (Make & Take), Darien Library, Free

Create a craft that you can give to a loved one during this holiday season! 4pm-4:30pm.

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December 20: Holiday Family Sing-A-Long, Darien Library, Free

Everyone will be laughing all the way as we sing old and new holiday songs with our jolly librarians! 10:30am-11:30am.

December 26: Kwanzaa Crafts, Darien Library, Free

Celebrate the holiday of Kwanzaa in the Children's Library with this special craft! 4pm-4:30pm.

December 27: Noon Year's Eve Party, Ferguson Library-South End Branch, Free

Children and their families are invited to a celebration counting down to the New Year without staying up late! Enjoy stories, crafts, music, and dancing, concluding with a balloon drop. 12pm-1pm.

December 31: New Year's Eve Party with Squeaky Clean, Norwalk Library, Free

Dance your way into the New Year with live music featuring the band Squeaky Clean. Join us for a countdown to noon to ring in the New Year just a few hours early! 11am-12pm.

December 31: Noon Year's Eve, Maritime Aquarium, Norwalk

The Aquarium is planning fun midday activities for families with young children who want to celebrate the end of 2018 together, but not at the stroke of midnight. From 11 a.m. to 2 p.m., a disc jockey will provide the beat, as well as a countdown to 12 o’clock; 12 o’clock noon, that is. Also on hand will be “bubble-ologist” Kim Winslow, strolling magician Greg Dubin, and strolling comedy/juggling by Peter Straus. 11am-2pm.

December 31: Noon Day's Eve, Darien Library, Free

Families are welcome to join us in the Children's Library for a fun countdown to "noon" as we get ready for the new year! Decorate a craft and have a snack as we celebrate together. Say farewell to 2018 and hello to 2019! 11:30am-12pm.

December 31: Noon Year's Eve Party, Ferguson Library, Free

It can be tough to make it all the way till midnight, so ring in the New Year with us a few hours early! 11:30am-12:30pm.

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