Old Town Winchester Named One of USA Today’s 10 Best Main Streets in America
WINCHESTER, VA — Old Town Winchester has officially been named one of USA Today’s 10 Best Main Streets in America, earning national recognition for its vibrant downtown, small business community, and walkable charm.
The honor comes as Old Town celebrates two major milestones: the 50th anniversary of the Loudoun Street Walking Mall and 40 years as a designated Main Street community, making Winchester’s program the oldest in the Commonwealth.
“This is a win for our entire community,” said Brady Cloven, Executive Director of Friends of Old Town. “It reflects the hard work of our small business owners, the dedication of local residents, and the support of partners like the City of Winchester, the Winchester Economic Development Authority, and countless volunteers. The momentum downtown right now is real—and this recognition helps shine a national spotlight on everything we’re building together.”
Old Town Winchester stood out among dozens of other downtown districts for its unique mix of historic architecture, locally owned shops and restaurants, cultural venues, and year-round events. The 10Best award was determined by a public voting process led by USA Today, with Old Town Winchester ultimately rising into the Top 10.
“We couldn’t be prouder of Winchester’s Old Town and Walking Mall,” said Mayor Les Veach. “For over 50 years, it’s been a place where people gather, shop, and dine. It’s also a fantastic setting for community events. It’s great to see Winchester’s historical charm recognized at a national level; it’s a tribute to our amazing residents, businesses, and visitors.”
The award is expected to bring new visibility to Old Town Winchester, further boosting tourism and supporting ongoing efforts to strengthen the local economy.
To learn more about Old Town and upcoming events, visit www.friendsofoldtown.org or follow @FriendsofOldTown on social media.