The Story Behind Winchester’s Wishing Trees

wishing trees 2025 pod

While visiting a Christmas village in Switzerland, Donnie was captivated by a simple yet powerful tradition: trees adorned with handwritten wishes from people of all ages. Inspired, Donnie brought the idea home to Winchester, determined to create a space where her own community could share their hopes, dreams, and even their burdens. This vision blossomed into the Wishing Trees, now a beloved feature of Winchester’s Winter Village, thanks to the dedication of Donnie, her daughter Kaleigh Fincham, and their family.

Planting Roots in the Community

In this episode of The Valley Today, host Janet Michael sits down with Kaleigh and Donnie from The Ivy Chest / The Ivy Room to uncover the story behind the Wishing Trees and the Kinder Village. Click here to listen. The conversation reveals how the project quickly grew from a handful of trees to a central part of the town’s holiday festivities. With the support of local sponsors like Meadows Farms, which donates the trees, and organizations such as Froggy’s Closet, the Wishing Trees have become a collaborative effort that brings together businesses, volunteers, and families.

Wishes That Speak from the Heart

As the conversation unfolds, listeners hear touching anecdotes about the wishes themselves. Some are lighthearted—children wishing for cookies or dinosaurs—while others are deeply personal, expressing hopes for healing, reconciliation, or simply more time with loved ones. The anonymity of the process, Donnie explains, gives people the freedom to express feelings they might otherwise keep hidden. Reading these wishes, Kaleigh and Janet agree, offers a window into the community’s collective soul, fostering empathy and connection among neighbors.

A Legacy of Giving Back

The Wishing Trees are more than a seasonal attraction; they are a tribute to Donnie’s late mother and sister, whose experiences with hardship and resilience inspired the family’s commitment to giving back. The Kinder Village, with its children’s activities and festive atmosphere, further extends this legacy, ensuring that every family—regardless of means—can experience the magic of the holidays. Despite challenges, including funding and logistics, the family remains steadfast in their mission, relying on sponsors and volunteers rather than city funding to keep the tradition alive.

Looking to the Future

The trio reflect on the impact of the Wishing Trees and brainstorm ways to expand the project, such as displaying wishes throughout December or creating a video archive of the notes. Their conversation underscores a central message: small acts of kindness and community spirit can transform lives. In Winchester, the Wishing Trees stand as a testament to the power of hope, generosity, and the enduring bonds of family and community.

A Festive Guide to Shopping Local in Old Town Winchester

Old town winchester Plaid Friday

As the holiday season approaches, Old Town Winchester is buzzing with anticipation. In a recent episode of “The Valley Today,” host Janet Michael welcomes Brady Cloven, Executive Director of Friends of Old Town Winchester, to discuss the exciting lineup of events and the importance of supporting local businesses. Their lively conversation happens at Winchester Brew Works and sets the stage for a season full of community, celebration, and unique shopping experiences. Click here to listen.

Plaid Friday and Windependent Weekend: A Local Alternative

Kicking off the festivities is WINdependent Weekend, a creative twist on the traditional Black Friday. Brady explains that Plaid Friday, the event’s opening day, encourages residents and visitors alike to don their best plaid and explore the vibrant shops along the walking mall. This initiative, he notes, is designed to spotlight small businesses as a meaningful alternative to big-box shopping. Shoppers can pick up a physical holiday shopping guide—courtesy of local sponsors—which includes a handy map and a retail bingo card, making the experience both interactive and rewarding.

Small Business Saturday and the Cookie Crawl

The excitement doesn’t stop with Plaid Friday. Small Business Saturday follows, featuring pop-up vendors, special deals, and the first anniversary celebration of Faire Isles Trading Company. Brady highlights the collaborative efforts of local businesses, from Moon Phased’s vendor pop-up to the Ivy Room’s partnership with Laura’s Lemonade. Moreover, the much-anticipated Cookie Crawl, in partnership with Knead Bread Bakery, invites participants to collect cookies from various retailers, culminating in a sweet reward and a chance to win a raffle.

Community, Collaboration, and the Power of Volunteers

Throughout the conversation, Janet and Brady emphasize the vital role of community volunteers and business owners in making these events possible. Brady shares how committees and subcommittees, filled with dedicated locals, work tirelessly behind the scenes. He also points out that supporting Old Town isn’t limited to shopping—sharing promotions, leaving positive reviews, and simply spreading the word all contribute to the area’s success.

The Magic of Old Town: Walkability and Unique Finds

Transitioning to the unique charm of Old Town Winchester, Janet and Brady celebrate the walkable nature of the district. With over 200 businesses in the primary and secondary districts, visitors can easily stroll from shop to shop, discovering everything from local art to the innovative “blind date with a book” at Winchester Book Gallery. The hosts encourage listeners to explore beyond the holiday rush, reminding everyone that shopping local is valuable year-round.

Festive Finale: Tree Lighting and Parade

The holiday spirit culminates with the Old Town tree lighting and Christmas parade, drawing families and friends together for a magical evening. Brady urges everyone to check the city’s website and social media for updates, as the festivities promise to light up the community in more ways than one.

Supporting Local, All Season Long

In closing, Janet and Brady reiterate the significance of shopping local—not just during WINdependent Weekend, but throughout the entire holiday season. They remind listeners that every purchase, review, and act of support helps sustain the businesses that make Old Town Winchester a special place to live, work, and celebrate.

For more information on upcoming events, visit Friends of Old Town Winchester on Facebook and Instagram, or check out their website: https://friendsofoldtown.org/ for a full community calendar.