There’s Snow Place like Tarpon Springs

Location: Tarpon Springs, Florida

Uniqueness factor: The rare opportunity to see snow in Florida! 

Snow in Florida - There's Snow Place like Tarpon Springs annual event

Who says a White Christmas is impossible in The Sunshine State? On the contrary, after living in Tampa Bay for several years, I quickly learned that you don’t have to travel up north. The best-of-the-best is the annual There’s Snow Place like Tarpon Springs, located in the small Gulf side community of Tarpon Springs about 40 minutes north of Tampa. On a side note, this town is home to many authentic Greek restaurants (my favorite is Mr. Souvlaki).

This event is super festive & wintry with falling snow, a snow play area with over 20 tons of snow, a snow slide, a lighted boat parade, and free carriage rides.

It’s impossible not to get into the holiday spirit with all the festivities on the lineup. This event just goes to prove that you do not need cold weather to feel like it’s Christmas. While the forecast may call for sunny skies and mild 70 degree temps, the feel-good vibe of the holiday season is in the air in Tarpon Springs.

I lived in Tampa for over 3 years and attended many unique holiday events. This was one of my favorites as I moved here from a cold city and was missing the excitement of a winter storm. Check out my Tampa holiday guide for the best boat parades, ice skating, and more. The Bay is another underrated Christmas destination.

Snowfest

Location: St. Petersburg, Florida

Uniqueness factor: You can sled down a real snow hill in a tropical climate

Snowfest in St. Petersburg - Sledding in Florida

Sledding in Florida? Sure there are plenty fake snow events throughout the state, but in one city, you can actually sled down a real snow hill. At St. Pete’s Snowfest, you can enjoy the rare opportunity in the sunshine state to sled down a hill made out of 64 tons of the white stuff. For all those transplants missing a traditional winter up North, this is the closest you can get to the real experience without a 10+ hour drive.

St. Pete offers several festive events including a Santa parade and Cookies with Santa for the kids. You can check out their holiday events guide for further details.

Nestlenook Farms

Location: Jackson, New Hampshire

Uniqueness factor: It’s the most gorgeous Hallmark-esque ice rink in the country

Nestlenook Farms ice skating rink in Jackson, New Hampshire

There is this hidden gem in New Hampshire’s scenic White Mountains region where you can take an old-fashioned sleigh rides and skate on a gorgeous Victorian ice rink. It’s called Nestlenook Farms and a visit here will transport you into a wintry snow globe.

The gorgeous 3 acre rink, reminiscent of scene straight out of Currier and Ives, is located on serene Emerald Lake in Jackson, New Hampshire. The beautiful backdrop of the snowy White Mountains creates the picture-perfect winter wonderland setting. In between skating sessions, you can warm up with a hot cocoa next to a roaring fire in the warming hut.

Your journey begins in a custom made Austrian sleigh complete with cozy fur blankets as you make your way around the serene grounds of the 65 acre Victorian estate. Sleigh bells are jingling, skaters are gliding by, all while old-fashioned chime music lingers on in the background. After your ride, you can explore the on-site snowshoeing trails and then warm up with a hot cocoa by the firepit.

Read more about about my day at Nestlenook. It’s a wonderful daytrip from Boston and Providence to escape the city hustle and bustle.

Chriskindlmarket

Location: Downtown Chicago

Uniqueness factor: It’s the largest seasonal holiday market in the country

Christkindlmarket in Chicago
I love the festive ambiance of this market

Chriskindlmarket is one of the most beloved Christmas traditions in all of Chicagoland. Since 1996, Daley Plaza downtown has been hosting the German style open-air market. This unique market is modeled after Christkindlesmarkt in Nuremberg, Germany, a street market which began in 1545.  It’s considered the best holiday market outside of Europe. Chicago’s version is now the largest seasonal holiday market in the country, drawing in over a million visitors per year.

At this festive fair, you can stroll around taking in the beautiful decor as you shop for handmade glass blown ornaments, old-fashioned nutcrackers, beer steins, and much more. And of course, you can treat yourself to all sorts of traditional German fare including Bratwurst, potato pancakes, Strudel, and Glühwein, a traditional holiday hot spiced wine. I love that you can order hot cocoa in a cute souvenir mug.

2025 souvenir mug at Christkindlmarket in Chicago
Christkindlmarket heart shaped souvenir mug for the 2025 season

Admission is free and the market is within walking distance to the fantastic Millennium Park ice rink, the grand Christmas tree, and the iconic holiday windows at Macy’s. I love skating at Millennium – admission is free and the city views are so pretty.

As a Chicago native, I have done my fair share of exploring during the winter season. This is my favorite time of the year to head downtown as there is so much going on.

Update: There are now 3 locations including the original at Daley Plaza, Wrigleyville, and Aurora.

Wreathing of the Lions

Location: The Art Institute of Chicago

Uniqueness factor: The annual wreathing of the lions the day after Thanksgiving kicks off the holiday season in one of the country’s best Christmas cities.

Wreathing of the lions in downtown Chicago

If you have ever strolled around downtown Chicago during the winter season, you have probably noticed the big beautiful wreaths adorning the lions which stand outside the entrance to The Art Institute. The annual “Wreathing of the Lions,” a popular local tradition which draws huge crowds each November. It has been going strong for over 30 years and is unlikely to end anytime soon. 

The event features live entertainment and complimentary hot chocolate. Don’t worry if you cannot get here for the actual ceremony as the lions remain dressed in their cute apparel through the New Year.

While you are here, definitely check out one of the country’s best art museums. Being a Chicago native, I’ve been to this museum countless times, but it never gets old. You really can’t beat the impressive collection here and the beautiful location nearby so many iconic attractions.