As the holiday season approaches, Old Town Winchester is buzzing with anticipation. In this 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.

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.