Oklahoma's Underrated Retirement Haven Is A Wildly Charming Route 66 Stop With Shops And Museums Near Tulsa

In a 2026 WalletHub study, the finance platform ranked Oklahoma as the second-worst state for retirees in America. That's not to say you can't find great places to retire in The Sooner State. They just tend to go under the radar, like Claremore, a small city about 30 miles from Tulsa. They also tend to be more affordable — Claremore's cost of living is around 10% lower than the U.S. average.

Claremore hasn't always sprung to mind when considering retirement havens around America or even the state of Oklahoma. Niche, an online school and college finder platform, ranks it the 20th best place to retire in the state. Despite this, Claremore still grades between an A and a B for overall livability, diversity, outdoor activities, weather, and cost of living on the platform. The city is starting to earn some deserved attention as a retirement spot, landing on a list of the six best cities for Oklahoma retirees by Senior Resource. WorldAtlas also recently called Claremore the "best small town in Oklahoma for seniors."

While its underrated nature may be changing, Claremore is still a lot less heralded than many other retirement destinations around the country. This is all part of its charm; the city has just over 20,000 people, retaining a small-town nature that works well with its roadside positioning on the iconic Route 66. That's right, retirees settling in Claremore have direct access to one of the world's most inspiring road trips, as well as the city's own unique museums, shops, and community atmosphere.

The original Route 66 ran for 2,448 miles from Chicago to Santa Monica, passing numerous fascinating destinations along the way. Claremore is one of these stops, encountered along Route 66 between Catoosa and Chelsea, a sleepy Oklahoma town with countryside beauty. Claremore welcomes road trippers with its historic downtown, where you'll find many preserved buildings now housing restaurants, shops, and museums. As a result, retirees may have to deal with more tourists than some other Oklahoma cities. But this position on Route 66 also gives the city a liveliness it might otherwise lack.

Shopping in Claremore ranges from national chain stores to cute downtown boutiques and community-led markets. Downtown's Lilac District is a popular spot if you enjoy browsing antiques and specialty boutiques. Back in the Day Antiques & Treasures is a highly rated store with multiple antique vendors selling Native American art, vintage clothing, jewelry, furniture, Western decor, trinkets, and more. Two shops down is Community Fibers, a wool and yarn store perfect for anyone who loves knitting or cross-stitching. Retirees can connect with the community at one of the store's free stitching meet-ups or knitting classes.

Downtown Claremore also has a lovely community feel. The city welcomes volunteers wanting to help with organizing its Main Street Program of local events, such as Halloween celebrations and street festivals with food trucks and artisan vendors. This area also features many Claremore legends on vibrant murals, adding to the local charm. Claremore summers can get quite hot and humid, so it helps to have numerous restaurants, cafes, and shops to escape the muggy weather. The historic Belvidere Mansion has the lovely Pink House for long lunches consisting of savory sandwiches, sweet desserts, hand-chopped salads, and quiche. You can also dine on delicious Southern and Creole flavors at Gibby's South in Your Mouth.

The Will Rogers Memorial Museum is considered the top thing to do in Claremore on Tripadvisor. This iconic Oklahoma cowboy has left an eternal legacy behind as a significant personality and contributor to American radio, cinema, philanthropy, literature, and more. At the time of writing, seniors aged 62 or older only pay $8 for entry to 12 galleries displaying the largest collection of Will Rogers memorabilia, artifacts, photographs, and manuscripts in the world. You can admire original Rogers-inspired artwork, watch some of his classic films, and see his extensive saddle collection.

Anyone interested in guns should visit the J.M. Davis Arms & Historical Museum, which houses the world's largest private collection of firearms (over 12,000). These include handguns owned by bank robber Pretty Boy Floyd, flare pistols, miniature and disguised firearms, blunderbusses, and even a Chinese hand cannon from the 1300s. You can also explore a range of other exhibits, including World War I posters, old saddles, beer mugs, and local Claremore historical artifacts. Afterwards, visit the free-to-enter Claremore Museum of History to browse a detailed exhibit on playwright and poet Lynn Riggs, who wrote "Green Grow the Lilacs," which later became the world-famous "Oklahoma!" musical. You can also learn about other Claremore legends, including singer Patti Page, astronaut Stuart Roosa, and philanthropist Helen Robson Walton. The museum also shares Claremore's early history through photographs and artifacts.

You can drive to Claremore in about 35 minutes from Tulsa, the wildly underrated Southern music city. The city has various accommodation options just outside downtown, including chain hotels and a bed-and-breakfast in the heart of downtown. Be sure to also explore other stops along Route 66, which is the go-to choice for a retirement road trip.