A stroll along nine blocks of Central Avenue just east of the river takes you through downtown, where antique brick mixes with midcentury modern. Shoppers hunt for vintage cowboy boots at Browser's Corner or for hand-painted martini glasses at Dragonfly Dry Goods. To the south, trendy design showrooms and cafés have cropped up in the old warehouse district. You can sit in a defunct elevator shaft at the Breaks Ale House & Grill and order locally brewed Pigs Ass Porter to wash down a spicy sandwich stuffed with chicken and andouille sausage.

Northeast of downtown, the C.M. Russell Museum holds one-fourth of the namesake artist's lifework—from paintings and sculptures to illustrated letters with folksy quotes such as "Good friends make the roughest trail easy." Nearby you can pick up the River's Edge Trail, which traverses 30 miles of the Missouri's shoreline, attracting bicyclists, joggers, and dog walkers. Threading past Black Eagle Falls, the path leads to the Lewis and Clark National Historic Trail Interpretive Center, where starting in October the exhibit Mammoth or Mastodon? will feature fossils and hands-on activities for children. Farther down the trail, more than 400 acres of prairie grassland and groomed lawn draw picnickers to Giant Springs State Park. The site is home to both one of the world's largest freshwater springs, which bubbles forth 156 million gallons daily, and one of the world's shortest rivers, the 201-foot Roe.

After sundown cross the Ninth Street Bridge into Black Eagle, where Borrie's, a candlelit supper club, serves handmade ravioli. For nightlife, the Sip-N-Dip Lounge in the O'Haire Motor Inn features women in mermaid costumes twirling in the pool behind the bar. Beware the Fishbowl, a nine-shot wallop served in a goldfish bowl on a stem that will have you thinking you're closer to the South Pacific than to the Missouri.