Let's Be Friends

In Old Town Winchester

Welcome to Old Town Winchester—where history, charm, and a vibrant community come together in the heart of the Shenandoah Valley. Locally owned shops, cozy restaurants, craft breweries, and inviting coffee spots make this downtown district the place to be. With new adventures and events happening all the time, there’s always something fun to explore

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Get Friendly

Won't You Be Our Neighbor?

Spend an evening with friends enjoying live music at one of our local breweries, catch an unforgettable show at Bright Box Theater, or make memories with your family at the Shenandoah Valley Discovery Museum. Love the great outdoors? Take a leisurely stroll down the car-free Loudoun Street Mall, unwind in one of our scenic parks, or explore the public art installations scattered throughout downtown. Feeling festive? Don’t miss one of our seasonal events, like holiday parades, art festivals, or live performances on the pedestrian mall. Why wait? Join us in Old Town Winchester and discover what makes it so special—we can’t wait to call you a friend!

Current Projects

01

Master Planning Project

We're working on a long-term plan to shape the future of Old Town! This project focuses on revitalizing our public spaces, supporting small businesses, and making sure Old Town grows sustainably while staying true to its historic charm.

02

History of Us

Self-guided walking tours that share the stories behind our historic buildings and beloved businesses!

03

Local Art Installations

Public art that brings creativity to every corner!

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Join us as a volunteer, sponsor, or event participant! There’s a place for everyone at Friends of Old Town, whether you’re looking to share your time, talent, or ideas. 

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