Two Passionate Visionaries Rekindle Winchester’s Christmas Tradition.

by | Nov 2023

RICKY TIPPS and Montana Medina’s childhoods were highlighted by the town’s treasured tree-lighting event and other festive traditions during the holiday season. However, as time passed, this beloved tradition gradually lost its brilliance. Motivated by nostalgia and a shared desire to reignite the holiday spirit, Tipps and Medina took it upon themselves to rekindle Winchester’s Christmas magic. 

“Growing up with Merry Little Downtown Christmas, my favorite part of the event was just the community involvement with the officers’ fire trucks. We’re doing our best to try to bring that same feel into it,” Tipps remarked. “It was one of the things that always stuck out in my memory growing up, and knowing that my dad was one of the ones that really pushed to get that here.” 

As passionate individuals, Tipps and Medina both possess a profound affection for their community and a firm commitment to reviving the cherished Christmas traditions from their upbringing. As the executive director of the Winchester Downtown Program, Tipps spearheads initiatives to promote local businesses and events. Medina, with the Oldham Theater, brings her creative flair to the table. 

In 2022, fueled by determination and a shared vision, Tipps and Medina embarked on a journey to resurrect the tree-lighting event. Their deep roots in the community and genuine love for the town’s rich history made them ideal torchbearers for this endeavor. 

“Both of our parents were very involved in the community. Last year, my mom was in the hospital for almost seven months with cancer. So just having somebody to pick up and be in that leadership role was really important and all the community needed,” Medina said. 

With unwavering passion and determination, they rallied local businesses, volunteers, and the support of government entities within the town. Despite obstacles and challenges, they embarked on a mission to create a heartwarming event that would unite the community and create lasting memories for families, mirroring their own childhood experiences. 

Their first tree lighting event was successful and attracted more than 2000 people to the historic Winchester square. Echoes of children’s laughter filled the air as they shared their Christmas wishes with Santa, carols rang, and other participants marveled at the glistening lights. The event received instant praise, reigniting the town’s festive passion and nurturing a revitalized sense of communal unity.

As the holiday season approaches, Tipps and Medina are gearing up for the second annual Winchester Tree Lighting event, and their enthusiasm is evident. The event is scheduled from 3 p.m. to 8 p.m. on the Friday following Thanksgiving, promising festive amusement and entertainment for families. The square will be off limits to vehicular traffic, making way for various activities promising to bring joy and delight to visitors of all ages. 

“This year, we’ve got so much more that we’re putting into it. We’re really excited about it,” Medina said. 

Attendees can anticipate various attractions, including Christmas carolers filling the air with festive melodies, Santa Claus lending an ear to children’s wishes, and the Polar Express train offering rides around the community. A unique feature, the Christmas Tree Forest, will guide visitors through an enchanting woodland filled with Christmas trees, each possessing a surprise: princesses for children to meet and take photos with. The event’s highlight will feature a live performance by local artist HunterGirl, infusing the stage with the essence of music and cheer. 

The event will conclude with the grand Christmas tree illuminated, an inspiring moment uniting the entire community. Local eateries will serve delectable dishes throughout the event, and a heated tent will provide a snug setting for families to savor their meals. It’s an immersive experience designed to evoke the warmth and cheer of the holiday season while highlighting the local businesses that sustain Winchester’s community. 

Winchester’s historic camaraderie and shared responsibility reminds us of a time when neighbors looked out for one another, something Tipps and Medina hope to preserve through this festive tradition. They envision a Winchester where children and adults can create cherished holiday memories for generations to come. 

“I work with a lot of these kids in my day job in the community, so seeing them is neat. And to know they have something to come to inspires me and makes me keep going,” Medina remarked. 

As anticipation for the holidays grows stronger, let us remember the true spirit of the holidays is about coming together, celebrating community, and making lasting memories. GN 

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