These nine cities offer galleries, performances and hands-on arts programs alongside beaches, trails and other outdoor amenities. Housing costs and state tax rules vary, so retirees will need to weigh the full budget.
Investopedia included all nine cities in its 100 Best Places to Retire list, which considered cost of living, healthcare access and community amenities. Arts access is one reason to visit or move, but it is only one part of a retirement budget. Readers weighing other lifestyle priorities can also compare these wine-country options.
Each city has a different mix of culture, housing costs, outdoor amenities and state tax rules. Retirement does not have to mean giving up a busy cultural life to keep costs in check.
Rehoboth Beach's seasonal calendar includes both the Sea Witch Festival and the Rehoboth Beach Jazz Festival, alongside its summer concerts.
Florida and the coast
In Bradenton, working artists shape the neighborhood experience. The Village of the Arts turns colorful homes into galleries, studios, stores and restaurants. Monthly Art Walks and seasonal events bring people there. Riverwalk Park hosts performances and BAM!Fest, while the Herrig Center for the Arts offers exhibits and classes. A current Bradenton city guide also lists the Manatee Performing Arts Center at 502 3rd Ave. W. That adds a theater venue to the city's performing-arts options.
About 58,000 people live in this Gulf Coast city. Nearby Anna Maria Island, the Manatee River and Palma Sola Bay offer beaches and boating. Florida has no state income tax. The source describes Bradenton's everyday costs as lower than those in other Florida retirement hubs.
DeLand has a different feel: a historic, walkable downtown about three hours from Bradenton and near Daytona Beach and Orlando. ArtWorks DeLand runs a cooperative gallery, workshops and classes. The Athens Theatre stages performances, and the Museum of Art - DeLand hosts lectures, workshops and Art After Dark. WorldAtlas says the annual DeLand Fall Festival of the Arts takes place on Woodland Boulevard and draws 150 artists. It also names the Athens Theatre and the museum as established cultural venues. About 45,000 people live in DeLand, with parks and miles of trails nearby.
Rehoboth Beach has about 1,400 residents. Its cultural calendar lasts beyond summer. The Rehoboth Art League, in Henlopen Acres, has galleries, studios, classrooms and a permanent collection. Clear Space Theatre offers productions and performing arts programming. The Rehoboth Beach Bandstand summer concert series is one of the town's events. WorldAtlas also identifies the Sea Witch Festival and Rehoboth Beach Jazz Festival as recurring cultural events.
The beach, boardwalk and walkable downtown sit alongside access to Cape Henlopen State Park and Delaware Seashore State Park. The town is described as relatively affordable for a beach destination. Coastal recreation is close at hand.
The City of Rehoboth Beach has published an official update on the impacts of a nor'easter. The notice addresses post-storm measures and damage assessment.
Mountain and river settings
Roanoke pairs a downtown arts network with the Blue Ridge Mountains. Art Project Roanoke offers classes, events, a gallery and artist studios. Mill Mountain Theatre and Showtimers Community Theatre stage productions. The city's permanent public art collection has more than 180 works, including pieces along the Elmwood Artwalk. The Taubman Museum of Art is downtown.
Roanoke has about 100,000 residents, plus access to hiking and water sports. Living costs are below the national average. The setting is a draw.
Winchester is a historic Shenandoah Valley town of about 28,000 people. Residents can visit community-run galleries and studios, as well as the volunteer-led Winchester Little Theatre. ShenArts Gallery supports local artists. The Typewriter Studio & Gallery offers pottery, painting, craft nights and workshops. ArtScape organizes public art. For outdoor time within the city, there are Abrams Creek Wetlands Preserve and Shawnee Springs Trail and Preserve.
La Crosse, Wisconsin, has about 51,000 residents and sits by the Mississippi River. The setting suits boating, paddling, fishing and birdwatching. La Crosse Community Theatre and the Pump House Regional Arts Center offer performances, exhibits, classes and other programming. In spring, Artspire La Crosse brings visual, interactive, dance, performing and literary arts to downtown Riverside Park.
Housing and overall living costs are below the national average. Wisconsin does not tax Social Security benefits. That matters to some retirees.
New identities and traditions
Bethlehem has a substantial arts scene rooted in its steel-town history. ArtsQuest offers classes and workshops. SteelStacks, a 10-acre arts and cultural campus at the former Bethlehem Steel site, hosts concerts and festivals. Musikfest runs for 10 days and features hundreds of performances across multiple stages, including some free events.
The eastern Pennsylvania city has about 80,000 residents, more than 40 parks and a walkable downtown with colonial architecture. According to the source, Pennsylvania's treatment of retirement income is generally favorable.
Iowa City's creative identity centers on writing and the University of Iowa. Its UNESCO City of Literature designation recognizes the city's literary tradition and international ties. The Iowa Arts Festival, Mission Creek Festival and Downtown Gallery Walk add to year-round options at the PorchLight Literary Arts Center, ArtiFactory and Iowa City Fab Lab. Hancher Auditorium hosts touring Broadway productions and dance performances.
About 76,000 people live in Iowa City. The downtown is compact, and trails link parks, lakes and other recreation areas. The city has plenty to explore.
Rapid City draws on Western and Native American arts traditions, with galleries, public art and classes. The Dahl Arts Center has visual galleries, performing arts spaces and adult classes. Open Art Studio offers a community workspace and a volunteer-led drawing group. The city's Downtown Art Walk is self-guided, and local galleries feature Native American art, crafts and cultural works.
Rapid City has about 80,000 residents and is near the Black Hills, Badlands and Mount Rushmore. Its cost of living is below average.
Compare the full budget
The population range is wide: Rehoboth Beach has about 1,400 residents, while Roanoke has about 100,000. Other measures show the scale of local amenities. Bethlehem has more than 40 parks, Roanoke has more than 180 public artworks, and DeLand's festival features over 150 artists and artisans.
Those figures describe the cities and their cultural offerings. They do not show total living costs or the services an individual retiree will need. The full budget matters.
State tax rules can change how much retirement income a person keeps, but they do not settle affordability on their own. Florida has no state income tax. Wisconsin does not tax Social Security benefits. Iowa offers exclusions for certain retirement income. South Dakota has no state income tax and does not tax retirement-account withdrawals, pensions or Social Security at the state level. The source describes Pennsylvania as generally favorable for retirement income.
Housing, healthcare access and everyday expenses still need to be weighed against those tax rules. Many of these cities offer classes, arts groups that welcome participation and recurring public events, not just occasional performances. Culture can be part of daily retirement life.
The right fit depends on what a retiree values: a coastal setting, a mountain region, a walkable historic center or a university-backed arts community. Local costs and taxes also have to work with their income. An active arts scene is a real benefit, but retirees still need to check the full household budget.
