In many towns, the sight of 35 women of a certain age sashaying along a sidewalk in purple dresses and red hats would stop traffic, but not in Jacksonville. In this lively, historic enclave in Oregon's southwest corner, a gathering of members of the Red Hat Society—a national organization of self-avowed sassy ladies over 50—is merely part of a cherished tradition of local color. This is, after all, a town that once required "fancy women and gamblers" to register at the marshal's office an hour before sundown.

But sassy ladies aren't all that's well preserved in Jacksonville, the site of the Pacific Northwest's first gold rush in 1852. Poised between the wooded foothills of the Siskiyous and the fertile fields of the Rogue Valley, the town of 2,200 is chocka-block with lovingly restored 19th-century wood and brick buildings, many of which now house galleries, inns, boutiques, and eateries.

In 1966, the entire town was declared a National Historic Landmark District—the first in Oregon—and just last year, the National Trust for Historic Preservation named it one of the country's 12 most distinctive destinations, along with Calistoga, Calif., and Beaufort, S.C. It's also a four-season destination, given its mild winters, full performing arts calendar, and outdoor recreation options.

Though Jacksonville was born of gold fever, it was pioneer farmers and merchants who built the friendly burg you see today. By 1880, the original rough-and-tumble mining camp had evolved into the largest town in southern Oregon, with a bustling commercial district that boasted many brick storefronts and shady backstreets lined with proper Victorian homes.

Not long afterward, though, the boom went bust when the main north-south rail line bypassed Jacksonville in favor of nearby Medford. Business dried up and locals scratched out a living during the Great Depression, going so far as attempting to extract the bits of gold remaining beneath the town by digging tunnels under yards and streets—tunnels that still collapse on occasion, much to the consternation of current residents. But such economic misfortune eventually proved to be a salvation: With money to modernize being unavailable, the town's wealth of pre-1900 buildings sat untouched, ready for the preservationist wave that gathered during the 1940s and '50s and finally broke in the early '60s.

You'll get a good feel for the town and its history on the self-guided walk outlined in a visitor center brochure. Along the way, you can poke around the cluster of shops, restaurants, and cafés in the old commercial district on California Street, shopping for a Victorian-inspired gown or hat at Loreli's or quaffing an Oregon microbrew at the Jacksonville Tavern. You can also peek at gracious homes like the Victorian Orth House and the arts and crafts TouVelle House that are now both comfortable bed-and-breakfasts; stop at Spa for a rejuvenating massage or facial; and linger in a hilltop cemetery whose pioneer tombstones are engraved with touching promises of a sweeter life beyond. You'll see relics of the past like Klamath Indian baskets of tule reed and porcupine quill at the Jacksonville Museum of Southern Oregon History, which occupies the former Jackson County Courthouse, and at the adjacent children's museum in the old county jail. Kids can actually handle pioneer artifacts and learn about Jacksonville native Vance "Pinto" Colvig, the original Bozo the Clown.

Jacksonville's busy performing arts scene is centered on Britt Gardens, once an elaborate Victorian Gothic estate belonging to the early Oregon photographer Peter Britt, the first person to capture Crater Lake on film. The house was demolished in the 1960s after two devastating fires, and the site—amid ponderosa pine and madrona—now hosts the Britt Festivals, a series of outdoor summer concerts featuring dozens of big-name performers in jazz, country, pop, and classical music as well as dance. With the highly regarded Oregon Shakespeare Festival running from late February to November about 15 miles away in Ashland, catching top-notch entertainment becomes an almost-year-round option.

Get a taste of the region's bounty along the winding back roads of the bucolic Rogue Valley. At country barns and produce stands, you'll find plenty of pears, one of the region's principal crops, and you can even tour Harry and David, a huge mail-order fruit and candy operation that owns 3,400 acres of well-tended Comice pear orchards. The area is also the oldest wine region in Oregon, and at low-key wineries like Valley View—known primarily for its cabernets, merlots, and other Bordeaux varietals—you'll often sip award-winning vintages while chatting with the folks who made them. One worthwhile food-related attraction is the Rogue River Valley Creamery, which offers samples and sales of the famous Oregon blue cheese that's been produced there since 1957.

If you're looking for outdoor fun, try a rafting or fishing trip on the nearby Rogue River, or take a hike in the 1.1 million-acre Siskiyou National Forest. In winter, local snow hounds head to the Mt. Ashland Ski & Snowboard Resort on the slopes of 7,533-foot Mount Ashland. It's a fairly easygoing, compact, and budget-friendly resort, with 200 skiable acres, 23 runs and an open bowl, a halfpipe and terrain park, a cozy day lodge, and an average annual snowfall of 300 inches. An added bonus are spectacular vistas that include lofty Mount Shasta more than 50 miles to the southeast.

Back in town, you can read and drowse by the fire at your inn before heading out for dinner. Jacksonville has several excellent restaurants, including Gogi's, which specializes in such seasonal Northwest fare as salmon with sherried corn relish and hazelnut-pesto vinaigrette, and the Jacksonville Inn, which offers a large menu of seafood, steak, and pasta dishes, as well as a huge wine list. Most places are fairly informal, but you can always dress up a bit if you want—say, in purple and sassy red.

Planning Your Trip

All phone numbers are in the 541 area code unless noted. Pick up AAA's Oregon & Washington TourBook and map. For additional information, contact the Jacksonville Visitors Center, 899-8118,www.jacksonvilleoregon.org.

Sleeps

Magnolia Inn, 245 N. Fifth St., 899-0255, (866) 899-0255,www.magnolia-inn.com.

Orth House, 105 W. Main St., 899-8665, (800) 700-7301,www.orthbnb.com.

TouVelle House, 455 N. Oregon St., 899-8938, (800) 846-8422, www.touvellehouse.com.

Eats

Caterina's, 505 N. Fifth St., 899-6975. Fresh Italian specialties. Gogi's, 235 W. Main St., 899-8699,www.gogis.net.

Jacksonville Inn, 175 E. California St., 899-1900, (800) 321-9344,www.jacksonvilleinn.com.

La Fiesta, 150 S. Oregon St., 899-4450,www.chilimanserrano.com. Family-friendly Mexican.

McCully House Inn, 240 E. California St., 899-1942, (800) 367-1942,www.mccullyhouseinn.com. Seasonal menu served in an 1860 house.

Pony Espresso, 545 N. Fifth St., 899-3757. Coffee drinks, light breakfast, and lunch.

Things to see and do

Harry and David's Country Village, 1314 Center Dr., Medford, 864-2277,www.harryanddavid.com.

Jacksonville Museum of Southern Oregon History, 206 N. Fifth St., 773-6536.

Mt. Ashland Ski & Snowboard Resort, 482-2897,www.mtashland.com.

Rogue River Valley Creamery, 311 N. Front St., Central Point, 665-1155, (866) 665-1155.

Spa, 235 W. D St., 899-7893, www.jacksonvillespa.com.

Valley View Winery, 1000 Upper Applegate Road, 899-8468, (800) 781-9463, www.valleyviewwinery.com.

Events

Oregon Shakespeare Festival, the Bard's and other playwrights' works performed in Ashland. February 22 to November 3. 482-4331,www.orshakes.org.

Britt Festivals, June 7 to mid-September. 773-6077, (800) 882-7488,www.brittfest.org.

Photography by Greg Vaughn

This article was first published in January 2002. Some facts may have aged gracelessly. Please call ahead to verify information.