Climb in the Gunks, NY
Technicolor foliage and pleasant dry weather mean prime time in the Gunks, New York's most beloved traditional climbing area, located several hours north of Manhattan. With hundreds of quality routes between 5.3 and 5.12+, there are options for all manner of rock jockey—and many afford famous views over the surrounding forest and countryside. Come afternoon, recover in nearby New Paltz, which offers restaurants, bakeries, and small-town charm.

Go Canyoneering in Utah and Arizona
The canyon country around Moab, Utah, is typically sweltering in the summer. In September and October, when kids are safely in school, the temps have plateaued and Utah's chasms are prime for exploration. Consider a one-day exploration of Lomatium Canyon, with labyrinthine passageways, water-crafted amphitheaters, and rare endemic plants like slickrock desert parsley. Alternatively, head further afield to the Robber's Roost area near Hanskville, where multi-day explorations reveal 19th-century cattle rusters' graffiti and Native American petroglyphs. Or hop to Arizona's Antelope Canyon, the most scenic--and most frequently photographed--slot canyon in the States.

Raft the Gauley River, WV
During the Summersville Dam releases in September and October weekends, the Gauley River becomes America's epicenter of whitewater rafting. Now, the river lives up to its moniker—the Beast of the East—with 100 big, technical Class III-V+ rapids—like Tumble Home, Shipwreck, and Heaven's Gates—in a matter of twenty-six miles. After the ride, head to nearby Fayetteville, a year-long hub of whitewater action, or to the New River Gorge, which has more than 1,400 sandstone sport and traditional climbs.

Canoe the Connecticut River, NH
In autumn, when the trees explode in their spectacular finale of color, leaf-watchers migrate into New England just as quickly as birds migrate out. Escape the lines of driving drones by renting a canoe and plying the Connecticut River, a serene, traffic-free thoroughfare through prime leaf country. Near North Star Canoe Livery (603.542.6929; www.kayak-canoe.com), which rents boats, Woodstock, Vermont offers cozy fall cheer at its best, with country inns, apple farms, and fall festivals.

Hike Anza-Borrego Desert State Park, CA
When fry-pan heat season comes to a close in autumn, reconsider any notion of the desert as empty by exploring Anza Borrego Desert State Park. A closer look at this Colorado desert landscape reveals more than dozens of species of cactus, but also golden eagles, mule deer, kit foxes, and bighorn sheep. The 3.5-mile Borrego Palm Canyon Nature Trail runs through mesquite and ocotillo and offers an enticing introduction to the subtle charms of the desert.

Sport Fish for Walleye on Lake Erie, OH
October marks the tail end of the fishing season on Lake Erie, reputed as the walleye capital of the world for its shallow waters and spawning rivers. If you've ever wanted a snapshot of yourself with a big fish, this is your chance—here, walleye can reach up to ten pounds. Arrange a chartered fishing boat from Ohio's shores to troll for the big fish as well as for yellow perch and smallmouth bass.

Road Bike and Taste Wines in the Okanagan Valley, British Columbia
October may not strike you as prime time to visit British Columbia, but look past Whistler: The Okanagan Valley, just north of the Washington border, is a bizarrely temperate oasis in this otherwise wet and blustery coast. Here lies the center of British Columbia's wine and fruit production, in full harvest in autumn. Taste pinots and ice wines typical of the region, and sample harvest fruits and veggies while road biking about towns like Osoyoos and Vernon.

Horseback Riding in Oaxaca, Mexico
Oaxaca is colorful in all senses—from the vibrant craft community, historical city architecture, and delicious local cuisine of tamales and rich chocolatey mole sauces. The Day of the Dead celebrations, which fall at the end of October and beginning of November, add even more spice. Watch dances and the array of traditional puppets, then head into the province's hills, like Parque Nacional Benito Juarez, where trails for horseback riding and trekking carve through the landscape.

Hike and Drink Beer in Germany and Austria
In recent years, Oktoberfest has become a beer-soaked spectacle of both locals and tourists, which is exactly why it deserves a humored peek at least once in a lifetime. Conveniently, Munich, Germany, is situated near plenty of ops for detox. Our choice: Drive west to pick up the scenic Romantic Road between Augsburg and Fussen, then cruise south for a taste of storybook Alps in Innsbruck, where all manner of hiking, biking, and view-ogling await.

Kayak and Hike through Vietnam
Thailand has long been a well-oiled tourist machine, luring folks with the promise of aquamarine waters, dramatic seaside karsts, and white-sand beaches. But now other countries in Southeast Asia, like Vietnam, are catching on and hosting tourists more readily—and now's the time to go. Kayak in Halong Bay, dotted with soaring limestone karsts, hike to remote hill tribes, and kayak and hike through Ba Be National Park, where a serene lake is surrounded by impossibly lush evergreen forests filled with exotic wildlife like civets and langurs.