Written by Cichele Fields - Published on November 30, 2023

The Tiptoe Winter Guard is a group of performers from all across the country who came together to perform with Macy's mascot Tiptoe the Reindeer at the 2023 Macy's Thanksgiving Day Parade. Learn more about their journey to Herald Square!

Hey everyone! I'm Cichele with the team here at Ensemble Innovations. I had the pleasure of joining the Tiptoe Winterguard at the 2023 Macy's Thanksgiving Day Parade this year to document their experience. Let's take a little behind the scenes look at the winter guard- who they are, how they got here, and what their day at the parade was like!

Watch a recap of our trip down the parade route below! We started about ten blocks north of the official start of the parade where we waited in a staging area for our turn to join the line up. Since we were just before Santa at the very end of the parade, we waited about two hours from the beginning of the parade at 8:30am to step off!

We got to see lots of performers and floats go by, include Brandy, the Roots, and many bands and dance groups. We lined up behind the Macy's Singing Christmas Tree at about 10:30am and started our trip down Central Park West. 

The parade turns east at Columbus Circle and continues down the South side of Central Park until it reaches 6th Avenue, where the crowds were enormous! Check out the video to see the winter guard in the shadow of Radio City Music Hall and other iconic sites as they traveled down the street. The team had five different routines that they rotated throughout the parade route, in addition to their full performance in Herald Square. 

After passing some very vocal colorguard enthusiasts, we picked up our buddy Tiptoe at 37th St., and she and her crew joined us for the rest of the parade to Herald Square. When we turned on to 34th St, we entered the TV quiet zone, and had to wait in position while Cher performed with the St. John's University Dance Team. What a cool experience!

The team performed live on television and in front of the crowd at Herald Square just before Santa at the end of the parade with Tiptoe and her puppeteers. 

Watch the whole experience here!

This was Jalen's first time performing in the parade, but he hopes it's not the last. Despite juggling his own rehearsals as a director, he loved being able to participate, and the chance to have an outlet to perform again himself. He kept his participation under wraps from his students so they were surprised to learn they'd see him in Herald Square on Thanksgiving morning. 

He shared many of his favorite memories, including when the bus bringing them into the city from their rehearsal site in New Jersey crossed over the Manhattan Bridge and someone played "Welcome to New York (Taylor's Version)," seeing Brandy, Cher, and other celebrities live and in person, and even shaking hands with Flava Flav after performing in Herald Square. 

He summarized his Macy's Thanksgiving Day Parade experience saying "It was a blessing to stand and spin in the sun and have fun doing it. I cannot tell you how blessed and grateful I am."

We loved partnering with the Tiptoe Winter Guard design team to create some stunning vibrant flags to complement their look in Herald Square, along with custom streamers, and S-Five Performance Jazz Shoes. 

Tiptoe's custom super swing flags were dye-sublimated with their signature blue to pink and purple design with white snowflakes on our giant swing flags. These also feature a Genesis 11000 pattern. This proprietary process fuses a sparkly foil into the fabric of the flags, adding dimension and shimmer without the weight and hassle of traditional payettes. 

The streamers were dye-sublimated with a custom blue and snowflake print on iridescent lamé fabric and specially designed for this event. 

S-Five Performance Jazz Shoes were developed by choreographer Michael Rosales, along with the team at StylePLUS, specifically for the wear and tear of outdoor use. Michael envisioned a shoe with traditional dance shoe flexibility, but with reinforced seams to stand up to the elements, and additional protection in places that jazz shoes typically tear when worn on rough surfaces. The S-Five is available in a variety of colors, including light, medium, and dark skin tone colors and black.