The Best Holiday Activities In The Woodlands Area — For Holi-Dates, Family Fun and Festive Frolics

While it may not always feel like a winter wonderland in The Woodlands, if you’re looking for a slice of northern enchantment, then the Ice Rink may just be the perfect spot.

Located at the Cynthia Woods Mitchell Pavilion, the 21,000 square-foot facility boasts a well-maintained ice rink that’s perfect for skaters of all abilities and decked out with festive adornments.

The Ice Rink opens for the season this Friday, November 21. To view available dates and times, and book tickets, go here.

Taking place this Saturday, November 22, at Town Green Park, the Lighting of the Doves Festival is sure to make for a magical and romantic holi-date or the perfect family activity.

The festival is a longstanding Woodlands tradition. It really kicks off any holiday season in The Woodlands, bringing the community together. Symbolizing peace, the ceremonial illumination of the giant doves is a display of wonder and light.

The night concludes with an appearance by Santa himself, arriving by sleigh down The Waterway, and dazzling fireworks that illuminate the sky.

For more information, go here.

Step into the Woodlands Resort’s Leg Lamp Lounge this season and you’ll feel like you’ve just stepped into a movie. This transformed space offers cocktails inspired by A Christmas Story that bring an extra dose of holiday cheer to the season.

Start with the Leg Lamp Glow, a gingerbread cocktail made with vodka, Kahlua, gingerbread liqueur, amaretto and a touch of ground ginger and cinnamon. Rimmed with a brown sugar cookie crumble, this drink will have you feeling sweet.

Other drinks to try include the Fra-gee-lay, served in A Christmas Story-themed cocoa mugs filled with boozy Italian coffee, and the Deranged Easter Bunny, a pink sparkling spritz garnished with a sugar rim, cranberries, and a sprig of rosemary. For something bolder, go for the Soap Poisoning Christmas margarita or The Oldsmobile Man, which is a winter twist on a classic old fashioned.

If you’ve got more plans after drinks and need a little caffeine pick-me-up then a Ho-Ho-Ho…No! espresso martini should keep you going.

Lastly, Don’t miss the Triple-Dog-Dare shots, served in a leg lamp shot glass. Ralphie’s dad would approve.

For a free musical experience that’s sure to get you in the holiday spirit, the Holly Jolly Jingle, happening December 4 at Cynthia Woods Mitchell Pavilion, just may be the ticket.

More than 500 student musicians from across all of Conroe ISD will descend upon the stage to provide an unforgettable night of music and holiday magic. Performing Christmas classics and carols to sing along with, it’s a cozy evening that will leave you feeling full of joy.

This event is free and no tickets are required. The show starts at 7 pm, but the gates open at 6 pm. For more information, go here.

For an upscale, intimate and elegant event, step into a winter wonderland at The Audrey for a Holiday Nutcracker Tea that’s sure to impress.

Taking place Saturday, December 6 and Sunday, December 7 from 10 am to 3 pm, you can sip on elegant teas, nibble on delectable bites and immerse yourself in the enchanting sounds of the season.

Be on the lookout for Nutcracker ballerinas, including Clara and her whimsical mice, who will be dancing gracefully through the dining room throughout the afternoon. With twinkling decor, seasonal touches and holiday sparkle adornments, every detail comes to life.

For more information and to book your table, go here.

What’s more romantic than taking a swan boat ride or kayaking down The Waterway? Well, during the holidays, the twinkling lights make the whole scene even more enchanting.

Enjoy a jingle boat kayaking adventure where you will search for gift-wrapped surprises placed along the shores. Or turn up the romance with a moonlight paddle boat experience.

Go here for more information and to reserve your space.

Deacon Baldy’s has had a holiday makeover done by Woodlands Style House, and it’s dressed to impress. Head on out to the perfect date or friends night out for immersing yourself in holiday cheer while enjoying your favorite on-tap brews and food truck dining options.

Plus, the decorations provide the perfect Insta-worthy photos with an “Elfie Selfie” backdrop, classic leg lamp, two decorated trees, an ornament installation and a full red and green checkerboard across the garage door windows.

Deacon Baldy’s is open Tuesday through Thursday from 11 am to 10 pm, Fridays and Saturdays from 11 am to 11 pm, and Sundays from 11 am to 9 pm.

Beginning this Saturday, November 22, make a visit to City Place to enjoy all the holiday decorations, especially the picture-perfect backdrops at the mixed-use center’s Gingerbread Village.

For more information on Gingerbread Village, go here.

City Place is also putting on its first Holiday String Symphony on December 12 at 6 pm and 7:30 pm. These two free 45-minute shows will feature Divisi Strings Quartet playing enchanting holiday music. Coupled with the dazzling lights and festive atmosphere, this immersive performance is the perfect Holi-Date or family night out.

For more information on the musical event, go here.

Take a walk through the enchanting Festival of Lights at the Woodlands Church beginning  this Friday, November 21.

Entry to the plaza area is free, while tickets for the Christmas path range from $10 to $20 for ages 4 and up. All proceeds benefit local missions in The Woodlands’ community.

For more information or to purchase tickets, go here.

If your schedule is too full before the holidays, but you still want to get a nice  holi-date on the calendar, then consider getting tickets for The Woodlands Resort Songwriters Festival happening December 29 through January 1.

This three-day celebration is an event of storytelling through music with intimate performances and conversations with the headliners Darryl Worley, The Frontmen and Neal McCoy. It will also feature other acclaimed songwriters.

Exclusive VIP experiences — receptions, meet-and-greets and dining — are also available.

The musical weekend crescendos with a festive New Year’s Day Brunch in the Grand Ballroom featuring a 14-piece live jazz band to usher in the New Year with style.

For more information and tickets, go here.

The sights of the season come to life with Holiday on The Waterway, a dazzling display of Christmas lights that transforms The Woodlands Waterway into a festive wonderland. Brought to life by The Woodlands Township Parks & Recreation Department, this enchanting attraction presents a variety of illuminated features to explore.

This holiday trail spans a mile and a half from Waterway Square to Grogan’s Mill Road. The display runs this Saturday, November 22 through January 4.

Here’s the lineup:

— Oversized Decorations: Marvel at illuminated bows and larger-than-life Christmas presents that make for perfect photo opportunities.

— Twinkling Tunnels: Walk or ride a trolley through magical light-filled tunnels on the north side of The Waterway.

— Festive Displays: Admire sparkling snowflakes, glowing icicles, and whimsical deer and trees lit up along The Waterway.

— Holiday Tunes: Smaller illuminated presents add to the festive atmosphere with built-in speakers playing cheerful holiday music.

— Sweet Treats: Refreshments and desserts are available on weekends from 5:30 pm to 8:30 pm in the South Plaza between The Pavilion and The Waterway.