9 Best Virginia Towns For Retirees

The best Virginia retirement towns are small enough to walk and full enough to keep you busy. Winchester keeps museums and a historic downtown within a short stroll in the Shenandoah Valley. Bristol offers live country music and senior golf rates that make weekday rounds affordable. Cape Charles trades the crowds for a quiet Chesapeake beach and a walkable Main Street. These nine towns give retirees an easy pace without giving up things to do.

Winchester

The Shenandoah Valley makes for a quiet and beautiful place to retire in Virginia. Few towns can match the mix of relaxing atmosphere with ample amenities like Winchester, near the border with West Virginia. The town comes alive in the spring for the Shenandoah Apple Blossom Festival. Bring your grandchildren by for a week of family fun and a chance to meet members of your community.

History buffs will enjoy putting down roots in Winchester, thanks to its numerous museums and historical attractions. The Museum of the Shenandoah Valley offers a look into how society and life developed and changed in the valley over the years, with art and artifacts from the 18th century and beyond. You can also take a tour of George Washington’s Office, which includes artifacts associated with Washington.

Staunton

Elsewhere in the Shenandoah Valley is the birthplace of President Woodrow Wilson and a wonderful retirement community: Staunton. Staunton appeals to retirees who enjoy arts and culture and want to spend the lion’s share of their time in museums or theaters. For unforgettable live performances, the American Shakespeare Center’s Blackfriars Playhouse is the place to be. Acclaimed local actors bring the Bard’s plays to life. The annual Staunton Music Festival also offers you the chance to hear many acclaimed classical works live on stage.

For museums, the Frontier Culture Museum provides an excellent look into colonial times in the community. The staff wears costumes to transport you back in time and make you feel like you’re living before America’s independence. For more modern history, the Woodrow Wilson Presidential Library gives you a tour of the Wilson family home, as well as some of his personal effects.

Bristol

Country music lovers, look no further than Bristol as your retirement destination. The US Congress recognized the town as the “Birthplace of Country Music” due to the contributions it made to the genre during its early days. You can learn all about that history at the Birthplace of Country Music Museum. There, you’ll find many antiques from the early days of country music, as well as recordings of some of the earliest country songs. For a taste of modern country, you’ll find it at the Paramount Bristol. The concert venue, housed in an art deco building, hosts some of the best classic and up-and-coming country artists.

Of course, there’s more to Bristol than just country music, as it also has an excellent golf course at the Clear Creek Golf Club. The club offers discounted senior rates on weekdays, allowing you to shoot 18 holes at an affordable rate.

Abingdon

Near Bristol, you’ll find Abingdon. The town is a cultural capital of the Blue Ridge Highlands area of Virginia. For live entertainment, you’ll find no shortage of it at the Barter Theatre. You’ll see the classics and modern masterpieces alike come alive on the stage, with some of the finest young actors in Virginia performing. And Abingdon comes together to celebrate the arts during the Virginia Highlands Festival. Seniors and kids alike gather to see live music, shop with the local vendors, and enjoy the celebration of what makes Virginia great.

Culture also exudes from the several museums and galleries in town. The William King Museum of Art houses an extensive collection of local art, and they hold workshops throughout the year to help you improve your art skills. The Arts Depot in town also has a nice local collection and is a popular gathering spot for many of the area’s top artists.

Middleburg

Horse lovers who want an elegant retirement will find their place in Middleburg, long known as the Nation’s Horse and Hunt Capital. Founded in 1787 in the Loudoun County countryside, the town keeps more than 160 buildings on the National Register of Historic Places, so a walk down Washington Street doubles as a tour of early Virginia. You can settle in for dinner at the Red Fox Inn & Tavern, which has poured drinks in the same stone building since 1728. Retirees who follow the horses can spend an April afternoon at the Middleburg Spring Races, held at Glenwood Park, the oldest continuous steeplechase course in Virginia.

The days off the calendar are just as easy to fill here. The National Sporting Library & Museum sits on a six-acre campus with a research library and a fine art collection devoted to horsemanship and field sports. Nearby, more than a dozen wineries surround the town, and Greenhill Winery & Vineyards is a short drive out for an unhurried afternoon of tastings. When December arrives, the whole community turns out for Christmas in Middleburg and its mile-long parade of riders and foxhounds down the main street.

Martinsville

NASCAR passions run deep in the South, and retirees who enjoy seeing a race live will find no better place to put down roots than Martinsville. Martinsville Speedway, just outside of town, provides one-of-a-kind racing when the NASCAR Cup Series visits. The short track hosts the Xfinity 500 during the Chase for the NASCAR Cup.

Outside of race weekend, there’s still plenty to love about retiring to Martinsville. The town is home to the Virginia Museum of Natural History, with fossils and exhibits that detail the geological history of southern Virginia. And for a day outside in the fresh air, take a stroll on the Dick and Willie Passage through some of the area’s best vistas.

Clarksville

If spending time outside is part of a happy retirement for you, look no further than Clarksville. The town sits beside the Roanoke River, one of the longest rivers in all of Virginia. The river provides ample opportunities for excellent fishing, with bass, trout, and catfish living in the waters. On the other side of the river from Clarksville is Occoneechee State Park. The park is ideal for everything from a day trip and hike to renting out a cabin for a romantic weekend surrounded by the beauty of Virginia.

If you need a break from the woods, the Kinderton Country Club is a great place to get outside and enjoy some golf. The course offers discounted rates for members, allowing you to play all 18 holes on a budget while enjoying other club facilities, including the pool and pickleball court.

Smithfield

Smithfield is famous for its pork industry as the home of Smithfield hams and the Smithfield Packing Company, the world’s largest pork processor. You’ll find some of the best pork food in Virginia at the Smithfield Farmers Market on the weekends. Whether you’re getting a meal from one of the local vendors or raw ingredients to cook at home, the pork is second to none in Smithfield. The town celebrates this heritage with several themed events throughout the year, including the Bacon and Bourbon Music Fest. The event has everything from live music to delicious pork dishes for an excellent October weekend.

There’s also plenty to do outdoors to help you stay active during your retirement. Golfers will find an excellent course at the Cypress Creek Golfers’ Club, with family memberships available for great golf and dining. And the Windsor Castle Park in town provides several acres of walking trails for a peaceful day out along the river.

Cape Charles

The Delmarva Peninsula is home to the welcoming Chesapeake Bay community of Cape Charles. The town is a popular retirement community thanks to its rustic charm, excellent eateries, and slower pace of life. The Cape Charles Natural Area Preserve, right outside of town, has plenty of trails that take you through the forest and offer excellent views of the bay. It’s an ideal way to stay active in retirement and get out and enjoy the calming properties of nature.

Inside town, you’ll also find plenty to do. The Shanty is a seafood restaurant with live music and fresh, locally-caught fish on the menu. Peach Street Books on Mason Avenue has an extensive selection of books to help you find your next favorite novel. And right down the street, you’ll find Moonrise Jewelry, with locally created jewelry and vintage pieces to spice up your wardrobe.

Retire in Luxury in Beautiful Virginia

In a large and diverse state like Virginia, there’s a retirement destination that matches your goals. Whether your ideal retirement includes museum visits, live music, time in nature, or golf, these nine towns are sure to offer everything you could want. The hardest part will be deciding which corner of the Old Dominion gets to keep you.