Virginia offers retirees a welcoming combination of favorable tax policies, natural beauty, and access to healthcare, even in its small towns
Social Security benefits are not taxed, and residents enjoy a retirement income deduction. Scenic mountains, coastal regions, and peaceful rivers provide a variety of backdrops for an enjoyable lifestyle.
A rich history, numerous cultural attractions, and a mild four-season climate make the state a preferred destination.
Proximity to Washington, D.C., adds to the convenience for those wanting occasional access to big-city amenities.
1. Abingdon
Abingdon ranks among the most inviting towns in Virginia for retirees seeking an active and fulfilling lifestyle. With a population of 8,376, it delivers a rare mix of artistic vibrancy and scenic mountain surroundings.
Cultural life here thrives through the Virginia Highlands Festival, the renowned Barter Theatre, and art galleries that keep creative energy alive year-round.
Outdoor lovers can take advantage of the Appalachian Trail and Virginia Creeper Trail, both offering miles of breathtaking views and opportunities for walking, cycling, or simply appreciating the beauty of the region.
- Population: 8,376
- Cost of Living Index: 83.7
- Crime Rate Index: 11.5%
Abingdon’s healthcare access stands out, with modern facilities ensuring retirees can maintain an active and healthy lifestyle. Residents often describe life here as a balanced mix of cultural stimulation, historical richness, and natural serenity.
Among Virginia’s small towns, Abingdon is a place where arts, history, and nature come together to create a rewarding retirement setting.
2. Bedford
Bedford ranks high on the list of Virginia towns that combine historical depth with scenic beauty.
Home to 6,657 residents, Bedford offers an inspiring backdrop shaped by the Peaks of Otter and the surrounding Blue Ridge Mountains.
Retirees often spend weekends exploring the National D-Day Memorial, wandering the well-preserved historic downtown, or joining in local festivals that keep community spirit alive.
- Population: 6,657
- Cost of Living Index: 93.6
- Crime Rate Index: 16.4%
Healthcare access includes both hospitals and specialized senior living facilities such as Cardinal Senior Living
Among small towns in the state, Bedford’s blend of heritage and natural attractions provides an enriching environment for retirees who appreciate a slower pace without sacrificing quality of life.
3. Woodstock
@krismariawanders This small mountain town is one of my favorites in Virginia! It’s located near plenty of great hiking, making it ideal for post-adventure food/beer. I strongly suggest the brew house, but the cafe is also delicious. There are several other local shops to check out too! For the history buffs- Woodstock has some pretty cool background. The town was established in 1761 and has the oldest courthouse (Shenandoah county courthouse) still in use west of the Blue Ridge Mountains. It’s one of the oldest towns in Virginia, and was supposedly named by George Washington! 👉🏼Have you been here yet!? #virginiacheck #exploreva #mountaintowns #smalltowns #woodstockva ♬ Falling Apart (Sped up Version) – Michael Schulte
Woodstock offers one of the most peaceful yet lively experiences among Virginia’s retirement towns.
With a population of 5,807, it delivers a blend of small-town comfort and engaging activities.
Residents enjoy time along the Shenandoah River, attend the Vintage Woodstock Festival, and explore Seven Bends State Park for hiking, fishing, and birdwatching.
- Population: 5,807
- Cost of Living Index: 89.2
- Crime Rate Index: 14%
Healthcare is available through local clinics and Shenandoah County hospitals, ensuring accessibility without the need to travel far.
Among Virginia towns, Woodstock stands out for retirees who value peace, community events, and natural beauty in equal measure.
4. Chincoteague
Chincoteague’s 3,344 residents enjoy one of the most distinctive coastal experiences among Virginia’s retirement towns.
Known for the wild ponies on nearby Assateague Island, it offers a lifestyle built around nature, quiet beaches, and abundant wildlife.
Retirees can take morning walks along nature trails, spend afternoons boating, and participate in seasonal festivals that reflect the area’s close connection to its coastal environment.
- Population: 3,344
- Cost of Living Index: 83.3
- Crime Rate Index: 9.9%
Healthcare needs are met by local clinics, with additional access to hospital systems in Accomack County.
For those seeking coastal towns that combine tranquility with outdoor activities, Chincoteague delivers an ideal balance.
5. Bridgewater
Bridgewater’s reputation as one of the safest towns in Virginia makes it appealing to retirees prioritizing peace of mind.
Home to 6,596 residents, it offers clean parks, such as Wildwood Park and Edgebrier Park, and scenic views along the North River. These areas are perfect for picnics, walking, and enjoying the fresh air.
- Population: 6,596
- Cost of Living Index: 90.2
- Crime Rate Index: 6.4%
Bridgewater Retirement Community and regional hospitals ensure convenient healthcare access.
Among Virginia’s small towns, Bridgewater offers the kind of structured, friendly environment where retirees can enjoy both safety and a strong sense of belonging.
6. Farmville
Farmville is one of Virginia’s towns that skillfully merges a vibrant college atmosphere with a relaxed pace of living.
Its 7,473 residents enjoy cultural and recreational perks, including High Bridge Trail State Park, Longwood University events, and educational experiences at the Moton Museum.
- Population: 7,473
- Cost of Living Index: 80.6
- Crime Rate Index: 12.9%
Medical facilities within and near Farmville cater to the healthcare needs of retirees. This college town offers a distinctive mix of youthful energy and laid-back living, making it a compelling choice among Virginia towns for retirement.
7. Winchester
View this post on Instagram
Winchester, though slightly larger with about 28,000 residents, still carries the essence of smaller towns in Virginia.
Its historical heritage is evident in Civil War sites, a vibrant downtown, and seasonal celebrations such as the Shenandoah Apple Blossom Festival.
Museums, local markets, and theaters contribute to an active cultural calendar.
- Population: ~28,000
- Cost of Living Index: ~95
- Crime Rate Index: Average for VA towns
About six medical facilities per 1,000 residents provide outstanding healthcare coverage. Retirees who want history, seasonal festivals, and an active community will find Winchester among the most dynamic towns in the state.
8. South Boston
South Boston is one of the most affordable towns in Virginia for retirees, with around 7,500 residents and a strong senior population.
River activities, local museums, and the World of Sports complex provide recreational options throughout the year.
- Population: ~7,500
- Cost of Living Index: ~85
- Crime Rate Index: Moderate
Healthcare is available through local facilities and Halifax County’s medical system. Among Virginia towns, South Boston offers a lifestyle that balances relaxation with opportunities for active engagement.
9. Vienna
View this post on Instagram
Vienna’s combination of suburban comfort and small-town atmosphere places it among Virginia’s best towns for retirees who want access to urban amenities.
Around 16,500 residents benefit from proximity to Washington, D.C., as well as cultural attractions like the Wolf Trap Performing Arts Center and numerous golf courses.
- Population: ~16,500
- Cost of Living Index: ~120
- Crime Rate Index: Low
Healthcare is top-tier due to Northern Virginia’s large hospital networks. Among towns that deliver both cultural vibrancy and natural spaces, Vienna is a strong contender for retirees seeking variety in daily life.
10. Rockwood
View this post on Instagram
Rockwood, with 8,685 residents, offers the advantages of small towns while being close to Richmond.
Retirees can enjoy outdoor recreation and birdwatching at Rockwood Park, along with easy access to local walking trails.
- Population: 8,685
- Cost of Living Index: 99.6
- Crime Rate Index: 11%
Richmond’s hospitals and clinics are nearby, providing healthcare security. Among Virginia towns, Rockwood is perfect for those wanting a peaceful lifestyle while staying connected to urban conveniences.
Summary
Small towns in Virginia present retirees with options that balance affordability, tranquility, and quality of life.
Coastal settings offer fresh air and wildlife, while mountain towns provide scenic beauty and outdoor activities.
Cultural hubs keep life vibrant, and accessible healthcare ensures long-term comfort.
Personal preferences, such as a love for the arts, history, or the outdoors, can guide the choice toward a town that feels like home for the retirement years.
