Cannot Miss Holiday Events in the Suburbs: Westchester and Fairfield Counties

December is a very busy month. No matter what holiday or holidays you celebrate, there’s always shopping, cooking, wrapping and decorating to do. Then there’s usually more shopping.

But in between all of your holiday chores this year, spend some time celebrating the season by checking out some of these awesome holiday events happening locally in Westchester County and Fairfield County. There’s so much to pick from, but these are my favorites.


Winter Wonderland in Valhalla, NY (Ongoing)

If you're only going to do one festive activity this holiday season, make it this one. Winter Wonderland is a nightly fun-fest happening from November 23rd through December 31st at the Kensico Dam in Valhalla, NY. For $20 a person entrance fee, you receive unlimited visits to each activity on offer - the Winter Wonderland Holiday Circus, the RangersTown Skating Rink (your admission even includes skate rental!), three carnival style rides, a Musical Light Show and a visit with Santa himself.  

The event brings crowds of over 100,000 visitors to it each year. Given that it starts nightly at 5pm and temperatures can get chilly in December, I recommend dressing warmly and possibly saving your visit for when your kids are old enough to stay up a bit later and get a little chilly without melting down like a snowman. One nice perk is that advanced purchase tickets for this event can be used any day that the event is open so I plan to save my visit for the warmest December evening I can find! We can’t wait to go!

Watch the Maccabeats Perform, Bedford, NY  (December 2nd)

On Sunday, December 2nd, the popular a cappella group, the Maccabeats, will perform Hanukkah songs as part of Chabad of Bedford’s larger Hanukkah celebration at the Chappaqua Performing Arts Center. The event will begin with a 3:15pm menorah lighting, followed by  the concert at 3:30pm. Tickets for the show are $18 per child over age 2 and $36 per adult.

Santa Visits Caramoor in Katonah, NY (Select Days)

The Caramoor Center for Music and Arts is a beautiful art and music pavilion beloved for its summer outdoor concert series. In December, the Rosen House offers two adorable holiday programs. From December 5th through 13th, at 1pm daily, there will be  Holiday Tea Musicales where gifted musicians play holiday music as guests enjoy a delicious tea service (hot cocoa with marshmallows available for the kids!) Tickets to this event cost $65 per person.

Then on Sunday, December 16th, Santa Visits the Rosen House! At noon and 3pm that day, Saint Nick is visiting Caramoor, and he’ll be bringing milk and cookies and a 30 minute holiday concert along with him. Tickets to this one are $10 per child and $15 per adult.

A Christmas Treasury in Katonah, NY (Select Weekends)

Also in Katonah, hit Muscoot Farm on the weekends of December 8th and 9th or December 15th and 16th for an evening of holiday cheer called “A Christmas Treasury.” The event includes performances of songs from Christmas movies by local actors and musicians and refreshments for sale. The 90 minute performance (with one intermission) is appropriate for all ages and tickets are on sale now for $15 per adult and $12 per child. Performances will be held at 4pm and 6pm on the Saturday dates and just 4pm on the Sunday dates.

A Christmas Carol in Sleepy Hollow, NY (Select Weekends)

During those same two weekends of December 8th and 9th and December 15th and 16th, Sleepy Hollow’s Old Dutch Church comes alive as noted storyteller Jonathan Kruk and his musical accompaniments share the story of Charles Dickens’ A Christmas Carol. Each performance lasts about an hour and costs $25 per adult and $20 for kids age 3-17.


Stew Leonard’s Tree Lighting and Menorah Lighting Celebrations, Norwalk, CT (November 27th and December 3rd)

On Tuesday, November 27th (!!), Stew Leonard’s Norwalk location will kick off its holiday season with its annual Tree Lighting Celebration. Arrive for a 5:30pm start that evening and delight in festive musical entertainment, complimentary hot cocoa and cookies, and a visit from Santa wielding candy canes.

Then join Stew Leonard's in Norwalk at 5pm on Monday, December 3rd for its menorah lighting. Rabbi Hecht of Beth Israel Temple will light the store’s 18 foot menorah, after which time guests can enjoy live music, song and dance and complimentary Kosher refreshments. All guests will receive a dreidel and chocolate gelt, too!

Heights and Lights in Stamford, CT (December 2nd)

Sure you’ve sat on Santa’s lap but have you ever seen him rappel down a 22 story high rise building? On Sunday, December 2nd, come to Downtown Stamford’s Landmark Square at 5pm to watch Santa, Rudolph, the Grinch and MORE as they each descend from one of Stamford’s tallest building.  From there, the crew heads up Bedford Street to Latham Park for holiday cheer and the official lighting of Stamford’s Holiday Tree.

Watch the Maccabeats Perform, Greenwich, CT (December 2nd)

You can also catch the Maccabeats a cappella group doing their Hanukkah performance at the Greenwich High School Performing Arts Center at 10:15 am on December 2nd. The event, sponsored by Chabad of Greenwich, also costs $36 per adult and $18 per child over age 2.

Take Part in the Lighting of Fairfield County’s Largest Menorah, Stamford CT (December 4th)

On Tuesday, December 4th at 6pm join the Chabad of Stamford in Latham Park for the public lighting of Fairfield County’s LARGEST menorah. Following the lighting, there will be hot latkes and applesauce and apple cider, as well as chocolate gelt for the children.

Holiday Tree Lighting at Wakeman Town Farm, Westport CT (December 7th)

I absolutely love this working farm and culinary center. Get on the Wakeman Town Farm newsletter ASAP to learn about all kinds of cool programming throughout the year. And on Friday, December 7th visit the Wakeman Town Farm from 4:30pm to 5:30pm for an hour long festival of sing-a-long holiday music provided by Westport elementary school students and Broadway actress, Susan Terry. Guests will be treated to hot cocoa, cookies and s’mores. And when the sun sets, the Wakeman Town Farm tree will be lit! This event is FREE and open to all!

The Essex Steam Train in Essex, CT (Ongoing)

The Essex Steam Train and Riverboat’s North Pole Express, located in Middlesex County is a VERY popular holiday event. In fact, at this point available dates are limited to post-Christmas dates only, and many dates sold out mere days after they went on sale in September. The train departs a few times each evening for a 90 minute journey to find Santa and Mrs. Claus. Along the way, there are holiday sing-alongs, hot cocoa and cookies, and finally, Santa and Mrs. Claus are picked up to join the festivities. Little ones are encouraged to come in their pajamas for these evening rides. Tickets start at $35.50 per person over age 1.

If you’re bummed about missing the train, consider instead the daylight weekend option of the Santa Special. This ride is a tad shorter at 60 minutes long and features more personal time with Santa and Mrs. Claus. Tickets start at $25 and there’s ample availability for this adventure right now. This is a good option for folks with younger kids or who missed out on the North Pole Express.

Holiday Theater in Stamford, CT (Select Dates)

On select dates from November 16th through December 15th, Stamford’s Curtain Call Theater will be putting on performances of Elf, the Musical. With tickets at $35 for adults and $17.50 for kids, this show is a nicely priced holiday family option and should be lots of fun. Evening performances begin at 7:30pm and additional 2pm shows are offered on weekends.

Downtown Stamford’s Palace Theater is featuring several holiday shows this year. On November 24th at 1pm and 4pm, you can see performances of A Charlie Brown Christmas. Then come back the weekend of December 15th and 16th for the CT Ballet’s The Nutcracker. And if that’s not enough, catch the family friendly A Magical Cirque Christmas on Saturday, December 22nd (show starts at 8pm so best for older children). The holiday fun continues with a Frozen Sing-A-Long on December 30th!

For those who want their holiday spirit ASAP, the Westport Country Playhouse is also featuring Ballet Etudes: The Nutcracker on December 1st and 2nd.

Greenwich Reindeer Festival and Holiday Stroll, Greenwich, CT (Ongoing)

Each suburban town has its own holiday festivities but I’m gonna pimp out my town’s festivities, not just because I live there, but because Greenwich does up the holiday season BIG. And non-residents are welcome and encouraged to join the fun.

Beginning November 23rd through Christmas Eve, Sam Bridge Nursery and Greenhouse in Mid-Country Greenwich becomes Santa’s Village! There are live reindeer, carnival rides and Santa shows up for photo sessions (beginning at $29.99 from noon-6pm weekdays and 9am-6pm Saturdays). The event kicks off with a Ribbon Cutting Ceremony from noon to 6pm on November 23rd.

If you prefer shopping to live reindeer, then hit the luxury shopping destination of Greenwich Avenue the weekend of December 2nd and 3rd for all kinds of shopping promotions and festive events to celebrate the Greenwich Holiday Stroll. For that weekend only, parking fees along the Ave are waived and it’s a really fun and festive way to get your holiday shopping started.

Santa and Sock Skating at Stepping Stones Children’s Museum, South Norwalk, CT (Ongoing)

Stepping Stones Children’s Museum is a lifesaver to parents of young children once the weather turns ugly. Each year, the museum celebrates the beginning of winter and the holiday season with adorable events for children. Usually included in the fun are visits from Santa AND, my personal favorite activity, a “skating” rink out in the museum’s back yard where kiddies can take off their shoes and “skate” around in socks!  Stay tuned for more details about what Stepping Stones has planned this year!

Festive Dining at Thomas Henkelmann, Greenwich, CT (Ongoing)

Thomas Henkelmann serves up classic French dining in fancy digs at the Homestead Inn, located in the ritzy Belle Haven area of Greenwich. It’s extremely festive and cozy during the holiday season. If you’re looking for a way to celebrate the season as adults, stop by here for a drink and dinner.