The 5 Best Places to Visit in October for Leaf Peeping—and Landmark Architecture

The best places to visit in October are towns that evoke a sense of autumnal magic. I remember the first time I noticed how the golden fall light could change a facade on a family trip to Galena, Illinois, sometime between the ages of 12 and 15. Growing up in a rural college town, fall meant a dramatic foliage shift, forgiving temperatures, and weekend road trips aplenty. Galena was within a day’s drive, offering the perfect mix of history, shopping, and sightseeing (more on that to come)... and the top of the limit of how long my brother and I could get along in the back seat. But it was walking down Main Street, which is at the bottom of three tiers of town built into rolling hills, when I felt the buildings and their time-worn curb appeal come alive as the sun strolled across the sky.This same seasonal magic can be found all across the country. From antique store-lined streets to neighborhoods where every architectural detail rewards a slower pace, the best places to visit in October pair peak fall scenery with the kind of thoughtful design that makes you stop, look up, and linger a little longer.Hudson, New YorkAn aerial view of Olana State Historic Site in Hudson New York Photo: demerzel21 / Getty ImagesHudson's compact downtown punches well above its weight when it comes to design. Start on Warren Street, where beautifully preserved 19th-century brick buildings are filled with the kinds of shops interior designers happily lose entire afternoons in. Browse vintage furniture and contemporary homewares at FINCH; hunt for Swedish, Belgian, and French antiques at Red Chair; and then stop into Les Indiennes for its block-printed textiles and globally sourced home décor. Just outside town, Frederic Church's Moorish-inspired masterpiece, Olana, remains one of America's most extraordinary artist-designed homes, where colorful tilework, dramatic interiors, and sweeping views are even more striking framed by peak autumn color. Cap off the day with a drink at The Maker Hotel, whose layered interiors mix Belle Époque glamour with collected antiques and rich textiles that feel made for sweater weather.Galena, IllinoisUlysses S. Grant's former home in Galena, Illinois Photo: JannHuizenga / Getty ImagesGalena manages to make even a quick coffee run feel like an architectural walking tour. The town's remarkably intact Main Street is lined with Federal, Greek Revival, and Italianate buildings whose ornate cornices, cast-iron storefronts, and tall arched windows have hardly changed since the 1800s. Browse the contemporary works at Outside the Lines Art Gallery before touring the impeccably preserved Ulysses S. Grant Home, where original Victorian furnishings offer a glimpse into 19th-century domestic design. Afterwards, hop aboard one of Galena's historic trolley tours to admire the stately mansions climbing the surrounding hillsides—many of which survived the town's mining boom virtually untouched.Santa Fe, New MexicoFall foliage dots downtown Santa Fe, New Mexico Photo: MonaMakela / Getty ImagesIf cities had signature colors, Santa Fe's would be terracotta. Nearly every corner is wrapped in sunbaked adobe, weathered wood, and earthy plaster, creating a palette so distinctive it deserves its own paint swatch. October's cooler temperatures make it the perfect time to wander Canyon Road, where the galleries showcase everything from contemporary sculpture to centuries-old Indigenous pottery and textiles. Beyond this, tour the restored rooms of the Georgia O'Keeffe Museum, marvel at the centuries-old adobe architecture of the Palace of the Governors, or book a walking tour devoted to Santa Fe's signature Pueblo Revival style to learn why the city's low-slung silhouettes have become one of the most recognizable architectural traditions in the country. Then settle into Bishop's Lodge, Auberge Resorts Collection, where reclaimed vigas, handwoven textiles, sculptural kiva fireplaces, and contemporary Southwestern interiors prove that centuries-old design traditions can still feel remarkably fresh.Carmel-by-the-Sea, CaliforniaThe beach near Carmel-by-the-Sea, California Phtoo: Juanita Turner Photography / Getty ImagesCome autumn, Carmel-by-the-Sea's storybook streets are blissfully quiet. You’re here for Hugh Comstock's whimsical fairytale cottages, complete with swooping rooflines, crooked chimneys, and hand-hewn details that feel lifted from a children's book—but the town’s creative roots will keep your attention for at least a long weekend. Take a docent-led tour of Tor House, the hand-built stone home of poet Robinson Jeffers, where rugged architecture and the dramatic Pacific coastline exist in storybook harmony. If you’re known for spending hours in a single art gallery, head to the Carmel Art Association, one of California's oldest artist cooperatives. An afternoon here, and it's easy to see why this tiny village has long inspired artists, architects, and designers alike.Woodstock, VermontThe Taftsville Covered Bridge in Woodstock, Vermont Photo: arlutz73 / Getty ImagesWoodstock's historic covered bridges and beautifully preserved Federal- and Greek Revival-era buildings are a reminder that good design never really goes out of style. Put a guided tour of Marsh-Billings-Rockefeller National Historical Park high on your list, where the mansion's richly detailed interiors, Frederick Law Olmsted-influenced landscape, and formal gardens tell the story of one of America's most influential country estates. Keep the design deep dive going at nearby Billings Farm & Museum—the beautifully preserved barns and agricultural buildings showcase quintessential Vermont craftsmanship.Residents of Sleepy Hollow, New York; St. Helens, Oregon; and Salem, Massachusetts, share tales of how Halloween tourism impacts their lives