The Best Places to Travel in October

By Patricia Doherty, Travel + Leisure

By late summer, many of us are looking forward to October and anticipating that chill in the air that makes us reach for a sweater or stash away our tired summer clothes. It’s a good time for a change of scenery as well as a wardrobe switchover. Many destinations are ideal in October, and it’s a pleasure to travel when nearly everyone else is back to school or work.

Making themselves even more appealing as destinations, cities stage festivals and special events. Some travelers seek those out, always looking for different experiences in new places. Music-based events are frequent in Nashville, and a few are scheduled in October, although any day there is fine for entertainment. Sun Valley, Idaho will host five days of music covering all genres, and at their Trailing of the Sheep Festival, folk music, and stories will entertain guests at the annual celebration.

Film festivals in Chicago and Edmonton attract fans from afar, and in both cities, there’s lots to do when the lights go on and the movies are over. Chicago’s museums, river cruises, and restaurants are bonuses for visitors. In Alberta, the Jasper Dark Sky Festival is an opportunity for more than stargazing, with concerts, workshops, lectures, and the possibility of seeing the Northern Lights.

San Francisco hosts exciting Fleet Week and all the beloved city has to offer, including a getaway to nearby Sausalito to relax and view the city from a different perspective. Heading south, Dallas presents its State Fair, a huge annual event befitting the state of Texas. In Gulf Shores, Alabama, October festivals celebrate seafood lovers’ favorite, Gulf Shrimp, and the area’s abundant wildlife. In Sonoma, California, the harvest will be nearly complete, and it’s time to taste wines and enjoy the autumn scenery.

Charleston, South Carolina’s history, atmosphere, and autumn weather make it especially attractive in October. It’s also a good place to get into the Halloween spirit with ghost stories and cemetery tours, at night, of course. Lastly, if you’re actually wishing for spring instead of autumn, you can head to New Zealand, where Auckland awaits with warming weather, outdoor activities, and spectacular scenery. With a bit of planning and a road map or airline ticket, you can choose not only how to be entertained, but which season you’d like to be in.

Charleston, South Carolina

Often leading the list of Travel + Leisure readers' favorite cities, the Holy City is at its best in autumn when comfortable temperatures invite strolling through its historic neighborhoods, the best way to experience Charleston. Founded in 1670 and named for King Charles II, the city gained its nickname when settlers came from England, Scotland, France,Germany, and Ireland. Tolerance for their various religions allowed settlers to worship freely and to build churches and synagogues, many of which are still standing. Famous for its Southern charm, cobblestone streets, historic architecture, and delicious Lowcountry dishes, Charleston is an ideal place to be for Halloween, a holiday that has become a favorite time to visit places where ghost stories and haunted cemeteries can be found. Bulldog Tours specializes in "ghost tours,” including their exclusive Spirit of Magnolia Cemetery, the first official walking tour of the graveyard. The Haunted Arsenal, U.S.S. Yorktown, and Haunted Jail tours include chilling stories that will entertain and frighten, as well as provide history about the spirits still inhabiting those locales. The Haunted Pub Crawl might be ideal for those who want to hear their scary stories along with a brew or two. Stay in one of the 16 suites at Zero George’s immaculately restored 1804 buildings, or at the quaint Andrew Pinckney Inn, French Quarter Inn, or HarbourView Inn near the waterfront. If there’s time, visit Magnolia Plantation & Gardens or Boone Hall Plantation for the autumn atmosphere of pumpkin patches and hayrides.

Book a Deal: Belmond Charleston Place, skylark.com, rates from $323/night with $100 food & beverage credit, daily breakfast

Alberta, Canada

This western province of Canada set in the Canadian Rockies is home to Jasper National Park, the world’s largest accessible Dark Sky Preserve and host of the annual Jasper Dark Sky Festival. From Oct. 18-27, visitors to the festival will be treated to music, a photography workshop, lectures, and plenty of stargazing opportunities. A Symphony under the Stars by the Edmonton Symphony Orchestra will be a magical experience and, speaking of magical, there’s the possibility of seeing the Northern Lights in October. Calgary’s Rocky Mountain Wine & Food Festival, Oct. 18-19, will present wines, spirits, beers, and tastings from local restaurants. The Festival moves to Edmonton on Nov. 8-9. The Edmonton International Film Festival (Sept. 26 - Oct. 5) will screen more than 150 films, including short, feature length, drama, documentary, comedy, studio, and independent films. For outdoor enthusiasts, the region offers hiking, boating, cycling, fishing, whitewater rafting, golf, and more, all among spectacular surroundings. For a thrill and a birds-eye view of Jasper National Park, take the Jasper SkyTram, Canada’s highest and longest aerial tramway, about ten minutes from the town of Jasper. There’s also the Banff Gondola and Lake Louise Gondola for more mountaintop vistas. The new Glacier View Lodge, located an hour south of Jasper, offers evening glacier tours and stargazing from their outdoor patio. Visitors who enjoy train travel can experience Alberta through Vacations by Rail programs. 

Sonoma, California

The grape harvest should be nearly complete in October, although weather, growing conditions, and readiness of the fruit determines the schedule each year. Autumn adds gold and orange tints to trees and vines, while daytime temperatures remain in the comfortable 70s, making it a lovely time to visit Sonoma County. The 45th annual Harvest Fair in Santa Rosa celebrates the season with tastings and competitions, from the Professional Wine Tasting of wines made from grapes grown in Sonoma County to the Grape Stomping Competition with teams vying for the $1500 prize or at least the creative costume award. Fans of the Peanuts comic strip will want to visit the Charles M. Schulz Museum to meet cartoonists, enjoy hands-on crafts, and check out Snoopy’s Gallery and Gift Shop. At Kendall-Jackson Wine Estate and Gardens in Fulton, visitors can taste wines or enjoy wine pairings with food, cheese, or chocolate to learn about the producer’s vintages and their own preferences. Near downtown Healdsburg, Flowers Vineyards & Winery offers a destination experience on its 15.5 acre estate that includes a hospitality house, winemaking facility, gardens, outdoor wood-fired oven, and educational culinary programs. Bricoleur Vineyards has just opened their 40-acre Russian River Valley estate which includes a pavilion, rose garden, and estate villa. Hundreds of wineries throughout the county are open for tastings, and lodging ranges from boutique inns to hotels. At the newly renovated MacArthur Place Hotel & Spa in the heart of Sonoma, guests can enjoy spa treatments, luxurious rooms, and several dining options.

Nashville, Tennessee

This always vibrant city is extra pleasant in autumn when summer crowds have fizzled, bachelorettes have do-si-doed out of town, and temperatures range from comfortable daytime upper 60s to low 50s in the evening. Kick off the month at the Whiskey, Wine and Cider Festival at the Bedford on Oct. 1. With proceeds benefiting the Emergency Access Fund to assist local breast cancer patients, the festival is a charitable good time. Music City lives up to its name this month with headliners such as the Breakaway Music Festival on Oct. 11-12 at Fair Park and a tribute to country music icon Dolly Parton at the Grand Ole Opry on the same date. Nashville’s annual Free Day of Music offers tunes for every taste from jazz to rock and country at the Schermerhorn Symphony Center on Oct. 20. The Bridgestone Arena presents Sir Elton John’s Farewell Yellowbrick Road Tour on Monday, Oct. 28. Football fans may choose to spend a day cheering on the Tennessee Titans at Nissan Stadium. With a multitude of restaurants in town, finding a delectable meal is easy. Southern barbecue is always a good choice, and a true Nashville original is hot chicken served in varying degrees of spice. Located in the center of downtown Nashville near lively bars and restaurants, the pet friendly Bobby Hotel offers exceptional service and modern eclectic design. An on-site café and restaurant serve up tasty dining options, and the hotel has a choice of bars including the unique rooftop lounge complete with a refurbished 1956 retro bus and views of downtown. The luxurious Noelle Nashville is another option, just steps from Printer’s Alley.

Book This Deal: The Hermitage Hotel, skylark.com, rates from $262/night with $100 resort credit, daily breakfast

Auckland, New Zealand

It’s early spring in the southern hemisphere, and there may be a chill in the air, but there’s the promise of warmer temperatures as the month progresses. You’ll be ahead of summer’s tourist season and higher prices while you enjoy the “City of Sails,” a nickname based on Auckland’s many marinas, sailboats, and boat owners. Auckland’s nearly fifty dormant volcanic cones look like grass-covered hills, and they provide places for hiking, exploring, and enjoying scenic views, while also serving as reminders of the Maori culture and history. On Mangere Mountain, the best preserved of the cones, stone walls remain from ancient Maori settlements. Rangitoto Island, off Auckland’s coast, is twenty-five minutes away by ferry. The largest of Auckland’s volcanic cones, the island offers walking trails, 360 degree views, and a huge forest of pohutukawa trees with red flowers that are part of New Zealand’s Christmas tradition. The iconic Auckland Harbour Bridge can be admired from afar, but you can also take a guided walk to its top or drop off via bungee cord, even dipping into the sea below if you choose. For restaurants, entertainment, a casino, and breathtaking views of the city, visit Sky Tower. Once you’ve seen Auckland’s zoo, aquarium, wineries, museums, and skyline, you might want to end your visit with a few days at a serene, luxurious resort. For that, we recommend Helena Bay Lodge, about 200 miles north of Auckland, less than three hours on State Highway 1 or forty-five minutes in the Lodge’s helicopter from Auckland International Airport. Superb dining, spa, private beach, and exquisite suites overlooking the bay create a relaxing and intimate environment.

Chicago, Illinois

Nicknamed “Second City” for reasons that include its being second in population to New York City in the late 19th century, Chicago is second to none when it comes to their favorite foods—deep dish pizza, hot dogs, and Italian beef sandwiches. October is an ideal time to sample those local delicacies as well as the offerings of the city’s many upscale dining spots. The 55th Chicago International Film Festival takes place Oct. 16-27 with more than 150 short and full length films from 50 countries. Thousands of runners, including a world-class elite field, will compete in the Chicago Marathon on Sunday, Oct. 13, with a course that takes them through 29 neighborhoods among nearly two million cheering spectators. Make time for a visit to the wonderful Art Institute of Chicago and the Museum of Science and Industry, both exceptional collections. Admirers of Chicago’s architecture will want to take advantage of the annual Open House Chicago, Oct. 19-10, an opportunity for visitors to enter more than 250 buildings, including mansions, skyscrapers, theaters, private offices, and usually off-limits exclusive clubs. A wonderful way to see the city is a river cruise presented by the Chicago Architecture Center, especially around sunset. Stroll along the new Chicago Riverwalk to enjoy the views, public art, restaurants, and the recently opened Community Market. Stay at the recently renovated Claridge House boutique hotel, originally designed in 1923, in the quiet residential Gold Coast section. Or enjoy the luxurious Ritz-Carlton, a short walk from Michigan Avenue and the beach along Lake Michigan. The enormous lake, which looks like an ocean from its shores, is the source of the cold winter winds that give Chicago its other nickname, “The Windy City.”

Book This Deal: The Peninsula Chicago, skylark.com, rates from $372/night with $100 resort credit, daily breakfast

San Francisco and Sausalito, California

Summer arrives late in San Francisco, making what we think of as early fall an ideal time to visit, with temperatures around 70 degrees and a bit cooler at night. Fleet Week, from Oct. 6-14, includes the largest parade of ships on the West Coast, led by the San Francisco Fire Department’s fire boat. An air show by the U.S. Navy Blue Angels, held on the waterfront between Alcatraz and the Golden Gate Bridge, is fully choreographed and includes a United Airlines 777. Additional events are an art exhibit, ship tours, concerts, and high school band challenge. Golden Gate Park hosts the Hardly Strictly Bluegrass Festival from Oct. 4-6, a free event for music fans. First time visitors want to walk over the iconic Golden Gate Bridge, ride a cable car, tour Alcatraz, stroll through Fisherman’s Wharf, and explore Chinatown, Union Square, and the historic Haight-Ashbury area. It’s also fun to browse the Ferry Building Marketplace and stop at a wine or fresh seafood bar. Just across the Bay by ferry, boat, or car, is lovely Sausalito with hiking, cycling, unique floating homes, galleries, and delicious dining. Stay at Casa Madrona Hotel & Spa overlooking Richardson Bay or at The Inn Above Tide, a luxurious boutique hotel, with views of San Francisco Bay, the city skyline, and Alcatraz from private decks. San Francisco’s many excellent lodgings include the classic Huntington Hotel on Nob Hill, the new Virgin Hotels San Francisco, St. Regis San Francisco, and Taj Campton Place with its Michelin-starred restaurant.

Book This Deal: The St. Regis San Francisco, skylark.com, rates from $387/night with $100 food & beverage credit, daily breakfast 

Gulf Shores, Alabama

With temperatures hovering between the high 60s and low 70s, diminished crowds and 32 miles of spectacular quartz sand beaches, Gulf Shores is the perfect fall getaway. Located on the southernmost tip of Alabama, Gulf Shores offers an abundance of water activities including jet skiing, parasailing, kayak and paddleboard rentals, and deep sea fishing. October kicks off with the Alabama Coastal Bird Festival held from Oct. 2-5, giving visitors the opportunity to learn about birds, alligators, wildflowers, dolphins, and more. The 48th Annual National Shrimp Festival, from October 10-13 features live musical entertainment, unique crafts, fine art, and jewelry. This free festival is a seafood extravaganza starring, but not limited to, delicious fresh caught Gulf Coast shrimp. Experience the beauty of nature at Bon Secour National Wildlife Refuge as thousands of sea turtle hatchlings make their journey to the ocean. Gulf Shores is home to enough picturesque public and private golf courses to satisfy even the most enthusiastic players. Dining options abound. The Gulf, located in Orange Beach, offers casual waterfront dining with a fusion of burgers, Mexican fare, and locally caught seafood. LuLu’s, owned by Lucy Buffet, is a family friendly waterfront restaurant with live music and a playground for the kids. In nearby Orange Beach, The Wharf entertainment district is a popular venue for dining, concerts, and shopping. Accommodations include the moderately priced and recently renovated ONE CLUB resort community.

Sun Valley, Idaho

Like many ski resorts best known for winter activities, Sun Valley is just as appealing during other seasons, and the beginning of autumn is especially lovely. Everything is a bit less crowded, and brisk mornings give way to sunny, warm days. One of the most unique fall events in the country, the Trailing of the Sheep Festival, will take place from Oct. 9-13. It’s a celebration of the season and an actual migration of sheep to their winter pastures. On Sunday at noon, 1500 sheep head down Ketchum’s main street in a parade that also includes sheepherders, musicians, and local groups. Sheep dog competitions, demonstrations, food, storytelling, and wool products are also part of the festivities. Later in the month from Oct. 16-20, the Sun Valley Jazz and Music Festival comes to town with performances of swing, big band, vintage jazz, zydeco, blues, folk, doo-wop, and just about every musical genre one could think of. Between festivals, there’s much to do: biking on paved, car-free paths, tackling the hundreds of miles of single-track mountain bike trails, hiking the hills, fly fishing, golf, and horseback riding, just to name a few of the activities that attract outdoor and adventure travelers. Sun Valley Resort offers a range of lodging, restaurants, spa and salon, shopping, water sports, and golf at the 18-hole Trail Creek and nine-hole White Clouds courses. The Sun Valley Inn has just reopened with larger rooms and updated furnishings, and other places to stay include the Lodge, cottages, condos, and townhouses. 

Dallas, Texas

Dallas is a big city that lives up to a big reputation. Stereotypically known for barbecues, cowboys, and football, Dallas is actually a major metropolitan city of over a million residents located in the Prairies and Lakes region of north-central Texas. October is one of the most pleasant months of the year in Dallas, and with comfortable temperatures and woods brimming with fall foliage, autumn color is a major attraction.Visitors take advantage of the colorfest at one of the oldest parks in the region, Kidd Springs Park. Nestled among trees and open green space, the park will play host to the Dallas Festival of the Arts, a free, two-day (October 26-27) outdoor local art and crafts event. From Sept. 27-Oct. 20, head to downtown Dallas’s Fair Park for the city’s biggest annual event, the State Fair of Texas. Each fall, millions of visitors descend upon the famous fairgrounds to enjoy all things Texas. From the world-famous midway, which plays host to more carnival rides and games than one can even imagine, to attractions like cooking contests and demonstrations, deliciously outlandish (and Instagram worthy!) food, and shows featuring everything from cars to cows, the State Fair, much like the city of Dallas itself, has something for everybody. For those looking to spice things up, head west to the Original Terlingua International Championship Chili Cookoff. From Oct. 28 - Nov. 2, this four-day foodie-friendly festival boasts live music, margaritas, barbeque, and the world’s best chili contest, hosted and judged by the Chili Appreciation Society. For anytime fun, the Bishop Arts District and Deep Ellum neighborhoods have been revitalized and offer a rich assortment of restaurants, bars, funky shops, music and street art. If a cowboy clad experience is on your list, head to the Fort Worth Stockyards National Historic District for the Red Steagall Cowboy Gathering and Western Swing Festival. Held Oct. 27-28, this annual celebration includes a rodeo, trail ride, wagon train, cowboy music, cowboy poetry, and much more.

Book This Deal: Rosewood Mansion on Turtle Creek, skylark.com, rates from $446/night with $100 food & beverage credit, daily breakfast.