Why Winchester

Winchester, Virginia isn’t just a beautiful and historic place, it also offers a unique mix of amenities that cater directly to the needs of the 55+ active adult community. And we’re not the only ones who feel that way – AARP ranked Winchester as a top place in Virginia to retire, and World Atlas placed it at the #1 spot.

According to World Atlas, whose list of Virginia’s best retirement locales focuses on communities with small-town environments and high-quality amenities, Winchester “ranks evenly across all boards, with a median home value of $338,015, … a 1% lower crime rate and A+ amenities.”

Winchester offers a great location with easy access to Dulles International Airport and Northern Virginia as well as scenic mountains and countryside right outside of town. Winchester has abundant small-town charm, but comes with an array of amenities for retirement-aged individuals.

Excellent Healthcare Facilities & Services

Valley Health Winchester Medical Center, Retiree Medical Services
Valley Health Winchester Medical Center

The Valley Health Winchester Medical Center is an award-winning hospital with services from advanced surgeries to physical rehabilitation. In additional to quality medical care, it boasts a Wellness & Fitness Center that offers state of the art equipment, classes, personal training, nutritional counseling, and 2 pools.

Valley Health Winchester Wellness & Fitness Center, Retiree Physical Therapy
Valley Health Wellness & Fitness Center

Art, Gardens, History, and Music – In One Place!

Museum of the Shenandoah Valley, Events for Retirees
Museum of the Shenandoah Valley Summer Concert Series

Another great asset for the town is the Museum of the Shenandoah Valley, centrally located yet with a historic manor house, gorgeous gardens, sprawling pastures, walking trails, and art and culture exhibits. This historic and lively facility has something for everyone with year-round events including the popular summer concert series on the lawn.

Vibrant Businesses in the Heart of Winchester

Old Town Winchester Walking Mall, Local Dining, Art, and Stores
Old Town Winchester Walking Mall

At the heart of Old Town Winchester is the Walking Mall, packed with small-town charm, local dining and entertainment, small businesses, and annual events. Whether you’re looking for original watercolor paintings and prints of the local scenery, or elegant Italian dining, the Old Town Walking Mall has plenty of local businesses to explore.

Wineries Throughout the Valley

James Charles Winery & Vineyard, Virginia Wine Country
James Charles Winery & Vineyard

Another perk of Winchester’s location in the Shenandoah Valley is the easy access to local wineries. With over 20 wineries (virtually all with breathtaking views of the valley) within a 40 minute drive of Winchester. This makes Winchester a perfect location for both the casual wine enthusiast and the connoisseur of Virginia vinos.

Golf Courses & Country Clubs for Active Socializing

Shenandoah Valley Golf Club

Winchester offers 5 scenic golf courses, one of which is a part of the Winchester Country Club. Memberships to the Country Club may also include multiple dining options, a large pool facility, indoor and outdoor tennis, fitness center, and of course an 18-hole golf course (depending on the membership level you desire). If golf is all you’re after, the other 4 local golf courses have no membership requirement and vary in course difficulty to match any golfer’s game.

Scenic Battlefields, Trails, and Hikes

Winchester, Virginia Hiking Trails, Walking Paths, Battlefields
Bear’s Den Trail in Bluemont, VA

For the active view-seekers, Winchester has 11 popular hiking trails nearby. These trails range from in-town walking paths of Winchester’s historic battlefields to mountain trails with overlooks of the whole valley. Whatever your level of activity, Winchester has hiking opportunities for you.