Go because… you get to experience “locals’ summer,” minus the tourists.
Summer has a way of stealing the spotlight in seaside Newport, which just hosted sailing’s round-the-world Volvo Ocean Race and has long seen its population swell June through August. But fall weather is what New Englanders brag about (ever visit in March?). Clink glasses of Bordeaux under lawn tents during the Newport Mansions Food & Wine Festival (September 20–23) or run waterfront streets during the marathon and half-marathon the city hosts October 7. Recover—from jogging or jugs of wine—at Gurney’s on Goat Island: The hotel spa offers 15 different massages and dry eucalyptus saunas. Alternatively, be ambitious and drive to Point Judith for a ferry to Block Island. Twelve miles off the coast, where street numbers aren’t a thing, you can sit in an Adirondack chair at Spring House Hotel, a sprawling inn high atop a hill, watching boats sail away from the harbor as the island starts to close up shop for the season. Don’t worry: You don’t have to leave until tomorrow. —Cassie Shortsleeve
Kansas City, Missouri
Go because… Leslie Odom, Ben Folds, and the Fab Five are going.
Kansas City doesn’t get too much attention (notable exception: hosting the third season of Queer Eye), but it’s time to change all that. To start: You’re going to Missouri, not Kansas. Watch when you book those flights. Check into one of the hot new hotels in town—try 21c Museum Hotel, “where photography and oil painting exhibitions are as important as the lobby bar,” says Traveler’s Erin Florio—or Crossroads Hotel, opening this October inside a former PBR brewery. Once you’re settled, make some time for the season-specific draws. It’s officially football season, and Chiefs fans are both diehard and non-obnoxious. Catch a game at Arrowhead Stadium, or if you prefer your touchdowns with a side of nachos, at bars like Westport Ale House or Tanner’s Bar & Grill.
As for typical fall activities, you can’t do much better than Louisburg Cider Mill’s 40th Annual Ciderfest, held from late September to early October. You’ll find live bluegrass music, a 10-acre corn maze, pony rides, and, of course, food galore. You’d be a sucker not to try their apple cider doughnuts. More of an indoors person? A) We get it. B) You’ll be happy to know that Kansas City Symphony’s 2018-19 season kicks off in mid-September. This year’s headliners include Leslie Odom Jr. (Aaron Burr!) with the symphony on Sept. 22, and a full orchestra backing Ben Folds a few days later. If you can’t make it to KC in October, at least try for Thanksgiving. The Plaza Lights ceremony is one for the bucket lists. —Caitlin Morton
Jackson Hole, Wyoming
Go because… you’ll only have to share this outdoor playground with the locals.
Jackson Hole, in a valley ringed by the Grand Tetons, is ground zero for adrenaline tourism. Until mid-October when the frost sets in, you’ll have cool nights and warm days perfect for hiking and biking the acres of trails within the Bridger-Teton National Forest, whose foliage will be en fuego. (Though hopefully not literally—check the latest on wildfires in the area.) You can still raft the Snake River, though you’ll want to wear a wetsuit on the whitewater segments, and fly-fishing is amazing right now. For the best valley views, take the Jackson Hole Mountain Resort Tram to the top and hike down, then refuel at Bar Enoteca, with its locally made charcuterie and superb wine list. Book a room right there at Four Seasons Resort and Residences Teton Village (hooray for off-season rates), just a mile south of the gate to Grand Teton National Park. The early morning wildlife viewing is unbeatable this time of year (expect moose and bison), and before dusk you’ll hear the elk bugling while they mate and migrate. Or stay in the town of Jackson at the boutique Hotel Jackson and spend an afternoon shopping the square for haute Western-themed leather accessories at Man Toy Shop or blankets at Pendleton, getting your buzz on at local watering hole, Local, before a dinner of Asian-flavored Italian at Glorietta (the kitchen is helmed by a Momofuku alum). No matter where you stay, a night at the iconic Million Dollar Cowboy Bar, with its giant taxidermy and honky-tonk dance floor, is a must. —Alex Postman
San Antonio, Texas
Go because… the city looks pretty damn good for 300.
San Antonio may be turning 300 this year, but the city’s historic Spanish missions don’t look a day over 263. Texas temps in the fall (in the 70s and low 80s) make it the perfect time to hop on a bike and explore the four colonial architectural icons beyond the Alamo that make up the seven-mile stretch of San Antonio Missions National Historical Park, Texas’s first UNESCO World Heritage site. Make Hotel Emma your home base—it’s smack in the city’s still-hot Pearl District, along the San Antonio River but just far enough from the ultra-touristy parts of the River Walk. Plan a taco crawl drive—Benjamin’s, Garcia’s, and Ray’s Drive Inn (for puffy, fried tacos)—of course. Then head to the city’s Dia de los Muertos celebration over October 27 and 28 to see incredible, colorful altars, a nod to the city’s original location and continued connection with Mexico. —Meredith Carey
Go because… the weather is perfect and the produce is prime (even if the Sox fans are insufferable).
Boston’s energy levels have a way of rising and falling with the momentum of the city’s beloved sports teams and right now, the Red Sox have the best record in baseball. Hotel Commonwealth, commandeering a corner in Kenmore Square, puts you within easy access of the park. If you can’t finagle tickets, dine in the area (you’ll still hear the cheers)—order some prime beef brisket and biscuits on the outside patio at Sweet Cheeks, happy hour oysters from the counter at Eventide (one of our favorite Portland, Maine exports), or snack bar eats at standing-room-only Fool’s Errand. For non-fans? The playoffs conveniently coincide with another known New England stunner: October. See the colors—trees ablaze and Boston in the backdrop—from Brookline’s hilltop Larz Anderson Park, along Jamaica Pond (pictured), or during the scenic drive out to historic Concord. There, Woods Hill Table, a rustic New England restaurant set in a former supermarket, greets diners with a crackling, stone fireplace and farm-fresh meats and cheeses. —C.S.
Puerto Vallarta and Punta Mita, Mexico
Go because… beach weekends don’t have to end once school starts.
This is when you want to be on Mexico’s mid-Pacific, just north of Puerto Vallarta, where you may catch a humpback migrating to warmer southern waters later in the season, and temperatures hover around 80 degrees (while the East Coast will still be weathering hurricane season). Resort areas, like Punta Mita, are taking measures to welcome new types of travelers, too. The gated community has kicked off an ambitious long-term plan to introduce five new hotels into the area to give travelers options beyond the traditional rental villas and big-brand titans the area’s known for (the first will be announced this fall). From there, you’ll be a 20-minute drive from Sayulita, a surfing village with the laid-back sophistication of Tulum 20 years ago and the best mahi mahi tacos anywhere at El Itacate, a cheery bar and restaurant a block from the beach. Or, start in Guadalajara and make a proper trip of it: Mexico’s stylish second city is just two hours from the beach (a fairly nondescript drive through the country, set to become way easier with the opening of a new highway in October). Come November 2, it hosts a Day of the Dead celebration you’d want to fly in for. —Erin Florio
Maryland’s Eastern Shore
Go because … it’s peak blue crab season.
Blue crab season may kick off in April, but it’s the fall months that fans consider peak. October is an optimal time for visiting, and not just because the weather will be perfect or the crowds have thinned: It’s when crabs are the fattest (read: meatiest), served at the best prices (they drop after summer ends). You can enjoy the state’s iconic food anywhere by the water, but St. Michael’s makes an ideal home base. The recently renovated Inn at Perry Cabin offers guests in-room fireplaces, a revamped spa, new tennis center, and a new championship golf course. Also in October, you can sample craft brews from the Eastern Shore at the Good Beer Festival (October 12 and 13) in Salisbury, about an hour from St. Michael’s; and the private Glenstone Mansion reopens October 4 in Potomac after a multi-year expansion. It’s added a new gallery, bookstore, and two cafes to the 200-acre site, a former fox-hunting estate that houses post-WWII and contemporary art, including outdoor sculptures by the likes of Ellsworth Kelly, Richard Serra, and Jeff Koons (free admission). —Corina Quinn
Great Lakes Via Amtrak’s Lake Shore Limited
Go because… slow travel is very in right now.
If you’re already in Boston, or up toward the Finger Lakes and Rochester, NY, then consider extending your trip with a train ride that takes less than a day and lets you track the changing of the seasons along the Great Lakes. Amtrak’s Lake Shore Limited has long been a popular run, connecting Chicago and New York City (with a Boston extension) while passing through Cleveland and Buffalo; but it’s everything in between that catches your eye. The route follows the Erie Canal and the Mohawk River in upstate NY, and hugs the south shores of Lake Erie and Lake Michigan. It may only be 10-12 hours of your life, but you’ll get an eyeful of the country’s rural beauty, especially if you sit on the right side of the train heading west. Time this trip for early to mid-October and you’ll get to catch the tail-end of peak fall foliage season in New York and the beginning of the best colors in the Midwest. And don’t forget to check out the new “contemporary menus” onboard (code for not stale sandwiches!). —Laura Dannen Redman
Skaneateles, Finger Lakes, NY
Go because… it’s an apple-picking, cider-tasting, fall foliage-spotting classic.
As the leaves turn and brisk autumn breezes move in this October, make your way upstate to Skaneateles, a small lakeside town in Central New York that looks its finest this time of year. Check into the Mirbeau Inn & Spa, evocative of a Monet painting with its willow trees, lily pad-strewn pond, and golden buildings cloaked in ivy. (Is this upstate NY or France?!) Enjoy a hot stone massage and the eucalyptus steam room, or camp out at the outdoor hot tub (which runs year-round, thanks to a roaring fireplace nearby). When you’re ready to explore, town is a 10-minute walk away. The lake’s bright turquoise waters (yes, really!) contrast beautifully against the fall leaves, so if the weather is in your favor (average high temp is 60 F), sit back and enjoy the views. For more seasonal activities, head to Beak & Skiff Apple Orchards in nearby Lafayette, where you can pick your weight in apples— Fortune, Golden Delicious, Fuji, Empire—in October. The orchard is also home to 1911 hard cider, and you can drink it fresh at the on-site taproom. —Bridget Hallinan
Prince Edward Island, Nova Scotia
Go because… your kids will love Green Gables, and you’ll love the oyster hour.
Prince Edward Island is a magical place, an emerald isle of farms and fields, fringed with red clay and pine forests. It requires just that little bit of extra effort to get there—we flew to Halifax, rented a car, and drove an hour and a half to the car ferry from Nova Scotia—that makes a week discovering its bays and beaches all the sweeter. Our house was on a lovely little bay at the eastern end of the island near the small town of Souris, which has the perfect lobster shack, and also near Basin Head beach, a sandy paradise for us and our six-year-old twins because of the shallow sandbars that extend far out, making paddling around an all-day possibility. We also rented bikes along the Confederation Trail, which runs the length of the island; went bay fishing (one of my daughters caught the single mackerel that was biting that day); and toured Green Gables—a real place even if Anne is not! At first my girls were skeptical (they’re not old enough to read the books or ship Anne and Gilbert—yet), but the verdict after touring the gardens and the charming house with its pantry and dairy and wee bedrooms: “I thought this would be boring, but it was fun.” My husband and I ate our weight in oysters, mussels, and lobster. (Interesting fact: PEI provides 55 percent of the oysters eaten in North America and 70 percent of the mussels.) At The Inn at Bay Fortune, we dined on chef Michael Smith’s open-flame, seven-course FireWorks Feast, preceded by “oyster hour.” For 60 minutes it’s all-you-can-eat Colville Bay oysters, so creamy, plump, and delicious. All I can say is, I did my part. —Sunshine Flint
Bonus! Cape Breton Highlands National Park, Nova Scotia
Go because… you’re already on Prince Edward Island.
Seeing as you’ll likely start and end your trip to Prince Edward Island in Halifax, it’s worth tacking on some extra days to head east instead of north. On the northern tip of Cape Breton Island, you’ll find the Cabot Trail, a 185-mile loop considered one of the most scenic drives in Canada. Leaf peeping? Check: At peak fall foliage, which generally hits around October, entire ridges blaze bright red and the sloping, winding roads offer constantly shifting views from multiple angles. Wildlife? Yep: Multiple species of whale come to hang out along Cape Breton’s northern coast in the beginning of summer and stick around through the end of fall. Best of all, if you need to get out of the car and stretch your legs, the Cabot Trail is criss-crossed with hiking trails of all levels, which will bring you deep into rust-colored woods and onto rocky cliffs for views of the North Atlantic. —Sebastian Modak
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