Stretched out on a poolside lounger, sipping a tall, icy beverage as the sun warms the grass-fringed deck, I squint behind my shades and imagine a swim-trunks-clad Don Draper emerging from one of The Horizon Hotel’s low-slung guestroom buildings and strolling over for a refreshing midday splash. Indeed, my Mad Men–inspired daydream fits right in with the retro ambiance of this carefully restored 1952 hotel. The only incongruity in this quintessential summertime scene is the snow blanketing the dramatic San Jacinto Mountains behind me. This is Palm Springs in the winter.

Starting in November, as the weather turns chilly and gray in much of the country, California’s low desert is at its loveliest, with daytime temperatures in the 70s or warmer, and nights cooling to the mid-40s. It’s the ideal setting for a relaxing day by the pool or in a spa, for outdoor dining, windowshopping and assorted recreational activities such as cycling around town—all of which are on my agenda for this trip.

It’s been a few years since I spent much time in the Coachella Valley’s well-known resort town, and a lot has changed in the past decade. I remember when it was mainly architecture buffs who were in the know about the trove of mid-20th century style tucked away on Palm Springs’ quiet residential streets, or the under-the-radar home furnishings consignment shops along the northernmost blocks of Palm Canyon Drive.

Flash forward to 2010, and that midcentury aesthetic now defines Palm Springs, as typified since 2003 by the home of the official visitors center. Originally a gas station—whose swooping hyperbolic-paraboloid roof resembles an exaggerated classic-Cadillac fin—the structure was designed by renowned architect Albert Frey, with Robson C. Chambers, and has marked the north entrance to Palm Springs since 1965.

Inside the center, you’ll find a display case of memorabilia collected by the 11-year-old Palm Springs Modern Committee (PS ModCom), a nonprofit organization that has worked to popularize and protect the city’s heritage as a magnet for some of the finest Modern architects of the 1940s–1970s. Palm Springs has long been a retreat for influential Americans (presidents Eisenhower and Ford both retired here) and Hollywood stars (including Frank Sinatra and his “Rat Pack”), many of whom embraced the design trends of that era and helped propel Palm Springs into the national consciousness.

I’ve come to the visitors center to meet Robert Imber, a passionate preservationist with an encyclopedic knowledge of the area’s architecture, who conducts the intimate Palm Springs Modern Tours. Growing up in the Midwest, Imber spent his childhood vacations with his family in Palm Springs, and was always drawn to the city’s “ongoing pioneer spirit and sense of opportunity,” an energizing aura that has characterized the American West for generations.

First, Imber provides a brief introduction to Desert Modern, a distinctive branch of architecture’s Modern movement that is notable for the use of glass, deep overhangs, and indoor/outdoor spaces embracing the area’s views, climate and elegant informality. Then we hop into his minivan and set off to explore the recent past. My tour companions are a couple of stylistas from the U.K., wearing groovy clothing that pays homage to the midcentury era’s starburst-, trapezoidand amoeba-shaped patterns. Their eagerness stokes Imber’s enthusiasm and makes our three-hour tour fly by.

Along the way, our guide evokes the city’s midcentury heyday as we view the tour’s 50 featured building exteriors, such as the 1962 William Krisel–designed “House of Tomorrow,” a saucershaped showcase that became widely known as the hideaway where Elvis and Priscilla Presley honeymooned in 1967. Imber has seen the interiors of most of Palm Spings’ landmark private homes, and offers inside knowledge gleaned from relationships with some of the region’s notable architects, such as E. Stewart Williams (1909–2005), who was actively working until 1996, and Donald Wexler, who still lives and works in Palm Springs.

After our riveting tour, I head back to my accommodations, also a feature on Imber’s itinerary and on PS ModCom’s colorful map of Desert Modern landmarks. The stylish 22-room Horizon Hotel was designed by William F. Cody as a friends-and-family retreat for Hollywood producer Jack Wrather (Cody, Frey, Krisel, Wexler and Williams constitute Desert Modern’s “big five” architects). A series of angular single-story buildings are laid out around a large central garden and pool space; most of the hotel’s 22 rooms opens onto a patio facing the pool. A 2006 restoration stripped away landscape clutter and replaced ’80s–style furnishings to restore a sleek modernity to the property while preserving the integrity of its original layout.

Relaxing in the hot tub to the soft strains of ’50s crooners wafting from hidden speakers near the poolside bar, I reflect on my new appreciation for Palm Springs’ architectural pedigree, and vow to return in February for the sixth-annual Modernism Week. Midcentury Modern aficionados from around the world will congregate February 17–27 for more than 50 different events that appeal to everyone from the serious scholar to the casual pop-culture fan. In addition to the event’s three-day Modernism Show—featuring vendors of vintage and reproduction Midcentury Modern furnishings, jewelry and clothing—there will be architecture tours, home tours, parties, lectures, films, fashion shows and an exhibition of flight-attendant uniforms from the ’60s.

The Palm Springs Art Museum, one of my favorite local cultural venues, also offers several exhibits that ought to entice desert sojourners. Not only is the building a notable E. Stewart Williams design, but the museum recently acquired the former home of Albert Frey, perched on the hillside behind the museum, which it uses for special events and fundraisers. “Steel and Shade: The Architecture of Donald Wexler,” on view January 29–May 29, will offer a retrospective of the architect’s six-decade-long career spent working within the unique demands of the desert climate. The show will include working drawings, photographs and models of some of his distinctive private residences, as well as of commercial projects such as the Palm Springs International Airport.

Other exhibits at the museum this winter season include “Richard Avedon: Fashion, Stage, and Screen” (through January 30, 2011), a look at the photographer’s iconic fashion and portraiture work, and “Photographing the American West” (through February 27, 2011), a collection of images dating back to 1866 that show the progression of photography’s role in defining the American vision of the West.

And the new year always kicks off on an exciting note in Palm Springs, as motion-picture professionals and movie buffs congregate for the Palm Springs International Film Festival. The 22nd-annual festival, January 6–17, will screen approximately 200 films from 70 countries, including most of the cutting-edge films that make a circuit of the famous Cannes, Sundance and Toronto film festivals. The Palm Springs audience’s pick for best narrative feature at the 2010 festival was the Swedish thriller The Girl with the Dragon Tattoo, which went on to become a box-office success.

Modernism Week, the art museum’s programming and the film festival are timed for the height of what locals call the “season,” when the city’s population is largest and tourism spikes. Once shunned in the summer due to high temperatures, Palm Springs is now a year-round destination, thanks to ubiquitous air conditioning. But Palm Springs truly comes into its own during the dry, warm winter. January, the “wettest” month here, sees an average of only 1 1/4 inches of rain. The snow that falls in the nearby mountains serves as glorious icing on a scenic cake, something to be seen—but not shoveled!

Many visitors still pack a parka, though, if only to experience the Palm Springs Aerial Tramway, one of the desert’s treats. The Tramway’s two cable cars revolve slowly as they each carry 80 passengers on a 10-minute, 5,873-foot ascent through four ecological zones to Mount San Jacinto State Park. Don’t be surprised to see passengers toting crosscountry skis, snowshoes and sleds onto the tram; on a winter afternoon, it’s not unusual to leave a balmy 70-degree lowland and arrive at a 30-degree snowy wonderland at the Mountain Station, which is located 8,516 feet above sea level and provides a 360-degree view of the entire Coachella Valley.

Both the upper and lower stations of the Tramway are architecturally notable and remain fundamentally unchanged since the Tramway’s debut in 1963: The Valley Station was designed by Albert Frey, working with John Porter Clark, and the Mountain Station is an angular chalet design by E. Stewart Williams. The revolving cars, however, are a 21st century improvement. If you ride the Tramway during the month of December, you’ll get to enjoy the enormous cone-shaped “tree” of lights atop the Mountain Station, along with caroling and other festivities around the decorated pine indoors.

Another holiday tradition in Palm Springs is the annual Walk of the Inns, in which visitors join with locals in a stroll through the Historic Tennis Club neighborhood, adjacent to downtown, which features eclectic and small hotels and B&Bs whose architectural significance ranges from early 1920s adobes to Desert Modern classics. This year the walk takes place the evening of December 9, and will feature refreshments, caroling and holiday decorations at each property.

Plus, the walk is always held on a Thursday to take advantage of crowds gathering for the nearby Villagefest, a longtime desert tradition. Every Thursday from October through May, four blocks of Palm Canyon Drive close to vehicles between 6 and 10 p.m., transforming this stretch of downtown into a street fair with food vendors, local artisans, street performers and quirky services, such as the popular “Ask the Rabbi” booth.

When morning arrives on my last day in Palm Springs, I am determined to enjoy the sun as much as possible, starting with breakfast alfresco—by dinnertime I’ll be back to the reality of leaf-bare trees and chilly temperatures. At The Horizon, a custom continental repast is served each morning in your preferred location: in-room, poolside or on your private patio. My French press coffee lasts just long enough for the San Jacinto Mountains to become fully illuminated by the rising sun, and then I set out on two wheels, partaking in a Palm Springs trend that perfectly embraces the town’s retro appeal. The desert’s flat terrain and mild weather are ideal for cycling, and vintage-style touring bicycles are everywhere you look. Residents use them for local errands, and many small inns have a fleet available for guest use. I rent a fatwheeled Electra “Townie” cruiser from Bike Palm Springs, which opened last year in the heart of town. Its fleet encompasses bikes for kids and adults, including tandems, all sporting cushy seats and upright handlebars. Rental (around $25 a day) includes a helmet and lock, plus a map of town and six designated bike routes.

My first stop is Moorten Botanical Garden, reminiscent of the funky roadside attractions of yesteryear. Established in 1938, this private arboretum features 3,000 varieties of desert plants from around the world, everything from delicate miniatures to towering giants, thriving in concentrated habitats along a self-guided nature trail dotted with pioneer relics, ancient fossils and whimsical objects. Handlettered plaques identify desert mainstays such as the creosote bush and jojoba, giant sprawling agaves (including Agave sisalana, the source of sisal ropes and mats), and the delicate specimens that flourish in Moorten’s climate-controlled “Cactarium.”

From Moorten’s, it is an easy pedal to nearby El Mirasol, home to, in my opinion, the city’s best Mexican food. I enjoy a lunch of chicken enchiladas mole, a not-sosecret off-menu favorite, on the restaurant’s outdoor patio. My plan is to work off the carbs by riding to the north end of Palm Canyon Drive to shop the many consignment and designer boutiques that entice professional and amateur decorators from around the state. I find Modern Way, A La Mod, Modern Home and other sources for vintage and reproduction goods in a few concentrated blocks. I always make time to check out Trina Turk, the hip L.A. designer who’s embraced Palm Springs and the midcentury craze by establishing twin boutiques in town—one clothing, the other home furnishings.

Though it is hard to tear myself away from that perfect-condition $1,400 Danish Modern love seat (I guess it wouldn’t have fit in the handlebar basket anyway), I know I’ve succeeded in seeing Palm Springs during its finest season. The temperate months of late autumn and winter offer a perfect escape from raw weather elsewhere in the country, and showcase a city that comes alive with the change of the season. Palm Springs’ culture, unique architectural heritage, and recreational opportunities are propelling this trendy getaway into a second century of stylish popularity.