The 3 Best Women-Owned Businesses Around Winchester

Women-owned businesses continue to play an important role in shaping the economic and cultural landscape of the Winchester area. From hospitality and brewing to catering and community gathering spaces, these businesses often combine entrepreneurship with strong local engagement and relationship-driven service. Featured in this year’s Star Awards, these women-led organizations have built loyal followings throughout Frederick County and surrounding communities by pairing operational expertise with distinctive visions rooted in creativity, hospitality and community connection.

Winchester Brew Works

Winchester Brew Works operates as a craft brewery and taproom in Old Town Winchester, producing a rotating lineup of small-batch beers that includes IPAs, lagers, sours and fruit-infused ales. Co-owned by Holly Redding and Bonnie Landy, the brewery has developed a welcoming, community-oriented atmosphere that includes trivia nights, local vendor collaborations and charitable events supporting area nonprofits. The business also stands out within the regional craft beer industry as one of the area’s few women-owned and brewed establishments.

Hideaway Cafe

Hideaway Cafe combines a coffee house, bistro and community gathering space within Winchester’s pedestrian mall district. The cafe serves locally roasted coffee, teas, breakfast items, sandwiches and baked goods while also functioning as a venue for local artists, musicians and open mic events. Under the leadership of owner Victoria “Vicky” Kidd, the business has cultivated an inclusive environment designed to support creativity, conversation and community engagement.

Jordan Springs Market BBQ & Catering

Jordan Springs Market BBQ & Catering blends the atmosphere of a traditional country store with a large-scale catering and barbecue operation serving the Winchester region and beyond. Owned by Olivia Landry since 2008, the business specializes in smoked meats, homemade sides and event catering for weddings, festivals and corporate gatherings. Landry’s leadership has helped expand the market into a regional hospitality brand while maintaining its local identity and longstanding connection to the Stephenson community.

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