In the decades since, city leaders have invested heavily in green energy and smart planning, creating a charming, walkable urban core that hugs the southern bank of the Tennessee River. “They made a concerted effort and now it’s really focused on technology,” says Michele Kephart, a sales manager at The Chattanoogan, a sumptuous downtown hotel that opened in 2001.“Dirtiest city in America”—not exactly a great selling point for tourists. But Chattanooga has come a long way since 1969, the year the federal government dubbed it the nation’s most polluted metropolis.

Today, trees line broad boulevards populated by electric shuttle buses, and urban pathways run along the riverfront, connecting residents to pretty pocket parks and manmade creeks perfect for kids to splash around in. Over it all rises Lookout Mountain, less of a mountain than a towering 84-mile plateau that stretches from Alabama in the southwest on into Georgia and then to the bend in the Tennessee where Chattanooga sits.

October is a favorite month around here, largely because of the gaudy hues of the trees that cover Lookout Mountain and the orange, red and brown patchwork of land you look down upon from its summit. The weather is also perfect—crisp and cool, but lacking the bitter edge of winter.

The Chattanoogan (1201 Broad St., 423-756-3400) sits on the site of an old foundry on the southern edge of downtown, where it’s gentrifying block by block. Stocked with three restaurants, conference amenities, a spa and indoor pool, it’s an ideal launching pad for exploring Chattanooga. $202-$248

The Dwell Hotel (120 E. 10th St., 423-267-7866), with just 16 beds, is the spot for a romantic getaway—partly because kids under 12 are not allowed unless you’re renting out the whole hotel, and partly because of the hotel’s midcentury modern design and furnishings. Each room offers a different retro feel. The Flamingo Suite features feathery chairs, pink pillows and bird-heavy wallpaper and art. $225-$270

Chattanooga Choo Choo (1400 Market St., 423-266-5000) served as the city’s train station between 1909 and 1970, inspiring the 1941 Glenn Miller song “Chattanooga Choo Choo.” After passenger trains stopped running, the property was converted into a hotel named after the tune; you can stay in a normal room or a converted Pullman train car. Toot, toot. $142-$188

Do

Start on the water, with a tour on the Southern Belle (201 Riverfront Parkway, 423-266-4488), a riverboat that chugs along the Tennessee to the Chickamauga Dam, built in the 1930s as part of the New Deal.

Climb Lookout Mountain on the Incline Railway (827 E. Brow Road, 423- 821-4224), one of the steepest rides in the world. On top, Rock City (1400 Patten Road, 706-820-2531) provides sweeping views of seven states, narrow paths through stunning rock formations and kitschy underground thrills. (Mother Goose Village must be seen to be believed.)

On another side of the mountain, hike through caverns to Ruby Falls (1720 Scenic Highway, 423-821-2544), a breathtaking underground waterfall.

If it’s raining, scope out the Tennessee Aquarium (1 Broad St., 800-262-0695, tnaqua.org) or the Hunter Museum of American Art (10 Bluff View Ave., 423-267-0968, huntermuseum.org), set on a bluff overlooking the river.

Dine

The star of Warehouse Row, a refashioned industrial building stuffed with shops and eateries, is Public House (1110 Market St., 423-266-3366), serving upgraded Southern comfort food and pouring some of the best Old Fashioneds around.

At Champy’s (526 E. Martin Luther King Blvd., 423-752-9198), the slogan is “Fortys & Fowl,” for its finger-licking-good fried chicken and 40-ounce beers.

Need a wakeup? Visit The Camp House (149 E. Martin Luther King Blvd., 423-702-8081), an industrial-chic coffee joint that doubles as a venue for live music and community get-togethers.

Chattanoogans swear by the burger at Tremont Tavern (1203 Hixson Pike, 423- 266-1996) on the north side; the owner opened The Feed Co. Table & Tavern (201 W. Main St., 423-708-8500) on the south side last year.

The Chattanooga Brewing Co. (1804 Chestnut St., 423-702-9958) serves a topnotch selection, with one draft always set aside for some type of hot habañero pour. Get spiced.