These nine cities pair access to wineries and wine trails with outdoor recreation and local amenities. Housing costs and state tax rules vary widely.
WineAmerica counts more than 10,500 U.S. wine producers and 763,080 acres of vineyards. Wine is produced in every state and the District of Columbia.
The financial trade-offs are local. Some cities have lower housing and overall costs; others offer a state tax feature that may matter to retirees. Taxes matter, too. They do not replace a personal comparison of housing, health care and other expenses.
Washington has no state personal income tax, but it does impose a business and occupation (B&O) tax on business activity-a separate consideration from retirees' personal tax bills.
Investopedia identified its 100 Best Places to Retire in 2026 using factors such as cost of living, health care access and community amenities. Winery access also shaped this wine-focused selection.
Vineyard regions
Pasco, Washington, sits near the Columbia and Snake rivers. More than 200 wineries lie within 50 miles, with the Yakima Valley, Prosser, Red Mountain and Walla Walla wine regions nearby. Cabernet Sauvignon, Syrah and Merlot are local specialties. The city has about 83,000 residents, plus outdoor recreation, museums and public art. Living costs are lower than in Seattle and many other West Coast cities. Washington has no state income tax. But the Washington Department of Revenue says the state taxes certain large capital gains. Wages and personal income are not taxed, but that does not mean all investment gains are tax-free, as explained in its Washington tax guidance.
Winchester, Virginia, sits at the northern end of the roughly 150-mile Shenandoah Valley Wine Trail. The trail has about two dozen wineries. The region grows Viognier, Traminette and Cabernet Franc. Winchester also has wetlands, trails, museums and historic sites. Shenandoah National Park is a short drive away.
In late September 2026, WineAmerica discussed using a member survey to rebuild ties with U.S. wineries and strengthen the association's role as a national voice for U.S. wine producers.
Amarillo is a gateway to the Texas High Plains wine region. Its wineries and the 15-member Texas High Plains Wine Trail offer tasting stops. The area grows Cabernet Sauvignon, Syrah, Viognier and many other varieties. Amarillo has about 205,000 residents, parks and an affordable lifestyle. Palo Duro Canyon Park is about 30 miles away. Texas has no state income tax.
Mountains and rivers
Roanoke, Virginia, puts more than 20 wineries within reach in the Blue Ridge Mountains. The Wine Trail of Botetourt County and Virginia's Blue Ridge Cheers Trail connect wineries with other craft-beverage stops. Hiking, mountain biking and water recreation are available near the Upper James River and Smith Mountain Lake. Museums and historic sites cover the region's Appalachian, African American, Civil War and railroad heritage.
La Crosse, Wisconsin, has vineyards among the bluffs and river valleys of the Driftless Region. Local grapes include Marquette, Frontenac, La Crescent and Frontenac Gris. The Coulee Region Craft Beverage Trail and Driftless Wine and Cheese Trail link wineries with other local producers. About 51,000 people live in La Crosse, along the Mississippi River. Housing and overall living costs are below the national average. Wisconsin does not tax Social Security benefits.
Knoxville, Tennessee, offers a base for exploring East Tennessee wineries and mountain country. The Great Valley Wine Trail starts in the city. Regional varieties include Chambourcin, Norton, Vidal Blanc and Muscadine. Fishing and boating are among the outdoor options. The city also has live music, theater, sports and downtown events. Living costs are below the national average. Tennessee has no individual income tax, so the state does not tax pension income, Social Security or distributions from 401(k)s and IRAs.
City access
Allentown and Pennsylvania's Lehigh Valley have more than 30 wineries. Five belong to the Lehigh Valley Wine Trail. Chambourcin, Riesling, Chardonnay and Vidal Blanc are among the region's signature varieties. Allentown has about 128,000 residents, an arts district, museums and parks. Coca-Cola Park and PPL Center host events. The city's cost of living is lower than average.
Spokane, Washington, pairs downtown tasting rooms and wine shops with access to eastern Washington vineyards. More than 15 wineries and specialty wine shops are within 10 miles. Regional favorites include Cabernet Sauvignon, Syrah, Merlot and Chardonnay. The city's Sip Spokane Passport program offers an alternative to a traditional wine trail. Spokane has about 230,000 residents, outdoor recreation and a walkable downtown. Washington has no state income tax. Its capital gains tax does not apply to retirement accounts.
Des Moines, Iowa, has Jasper Winery within the city. Several other wineries are a short drive away, including stops on the Heartland Wine Trail. Marquette, Frontenac and La Crescent are among the grapes suited to the region's climate. Iowa's capital has about 200,000 residents, an arts and sports scene, more than 800 miles of nearby scenic trails and dozens of parks. Its cost of living is below the national average.
Wine access is only one part of a sound retirement move. Pasco and Spokane offer a broad Washington wine scene. Winchester, Roanoke and Knoxville pair wineries with mountain recreation. La Crosse offers river-country scenery and below-average costs. State tax rules can add to a location's appeal, but retirees should weigh them alongside housing, health care and daily expenses. The September 2026 tax-policy report from The Chronicle said the state Department of Revenue had warned of political and legal risks tied to proposed high-income-tax provisions. Washington's tax rules remain part of an ongoing public debate.
Check state tax differences before relocating. A state with no individual income tax does not automatically have lower household costs. Tax treatment can depend on income type and individual circumstances. A below-average cost-of-living measure also does not guarantee that a particular home or health care arrangement will be affordable. Compare the expenses that matter to your household, not just a citywide label.
