Map it out. Stop by the Cañon City Chamber of Commerce (403 Royal Gorge Blvd.; 800/876-7922), housed in the elegant abode of long-ago Colorado governor James H. Peabody, for a quick orientation and a walking-tour map of the historic downtown district.
Art vieux, art nouveau. Housed in the classic 1932 post office building (on the National Register of Historic Places), the Fremont Center for the Arts (closed Sun-Mon; $1; 505 Macon Ave.; 719/275-2790) is the nation's oldest continually operating community arts facility―and an excellent place to view work by Colorado artists. The newest venue in town, Bluäche Gallery (closed Mon; 301 Main St.; 719/429-3772), opened this May and features the sculptures of proprietor Mikel Williams and other local artists.
Flavor of the monks. The first crop of Rieslings is still on the vine at the brand-new Winery at the Holy Cross Abbey (2951 E. U.S. 50; 719/275-8631), but the tasting room is open, featuring a selection of Colorado wines. Enjoy a few sips, then tour the grounds of the monastery, home to Benedictine monks since 1924.
Take a dive. Celebrating its 100th anniversary, the Owl Cigar Store (closed Sun; 626 Main; 719/275-9946) grills up the best $1.80 double cheeseburgers in the West. Wash 'em down with a cold beer, then play a game of pool.
Cliffhanger I. Gaze into the abyss from the middle of the Royal Gorge Bridge & Park ($17; 8 miles west and 4 miles south of Cañon City off U.S. 50; 719/275-7507). Opened in 1929, the attraction carries a whiff of tourist-trap cheese; avoid the shops and snack bars and concentrate on the views, which will stun you.
Cliffhanger II. Keep both hands on the wheel on Skyline Drive (turn off U.S. 50 about 3 miles west of Cañon City), a knife-edge road built by chain-gang laborers in the early 20th century. Pull off at the first turnout to see 100 million-year-old dinosaur tracks.
Sign language. The billboards for Merlinos' Belvedere Restaurant (1330 Elm Ave.; 719/275-5558) line the road for 20 miles before you get to Cañon City. Follow them. This family-owned emporium of homemade pastas and aged, hand-cut steaks more than lives up to its billing.