Fall 2026 Story Starters – Canada Edition

NORTH AMERICA 

Boston, Massachusetts – https://www.meetboston.com 

Fall foliage takes over historic Boston (Sept.-Nov.) across Boston’s Public Garden, Beacon Hill, Back Bay and nearby Cambridge, turning them into prime leaf-peeping destinations, offering Canadians a classic New England fall experience without venturing far from the city.  

For culture seekers, Boston Film Festival (Sept. 17–21) celebrates its 42nd year with world premieres and emerging filmmakers, adding a strong arts-and-culture angle to a September visit. Open Newbury Street (select Sundays through Oct. 11) becomes pedestrian-only on select Sundays, allowing visitors to explore one of the city’s most vibrant shopping and dining districts car-free. For bigger events, Head of the Charles Regatta (Oct. 16–18) takes over the Charles River with the world’s largest three-day rowing event, attracting more than 11,000 athletes and hundreds of thousands of spectators. Boston Book Festival (Oct. 17) is one of New England’s premier literary events at Copley Square with author talks, readings and cultural programming, making it an ideal fall getaway for Canadian book lovers.  

Boston is welcoming the world’s first restaurant named after Quebec’s biggest star as Celine opens in Fort Point (Fall 2026). Named after Céline Dion, the new restaurant at Boston’s Fort Point neighbourhood brings Montréal influences, elevated tavern fare and a strong cocktail program to one of the city’s fastest-growing dining districts. The Canadian connection makes it a particularly relevant food story for travellers from north of the border. The Museum of Fine Arts Boston features a blockbuster exhibit, “Picasso, Miró, Dalí: Unbound” (through Jan. 24, 2027) to bring together works by three of Spain’s most influential artists, creating one of the city’s marquee cultural experiences for fall 2026.  

Expedia Group – www.expedia.ca  

The Expedia Travel Agent Affiliate Program (TAAP) is redefining its role beyond a booking platform, introducing new capabilities that help travel advisors and agencies streamline back-office operations, reduce manual work and scale their businesses more effectively. With the launch of its back-office API and a new feature that lets advisors add their own internal reference codes to bookings, Expedia TAAP connects booking data to their existing systems while improving tracking, reporting and reconciliation of bookings and expected earnings. The tool frees teams from manual reconciliation and fragmented processes, allowing them to focus more on higher-value activities such as client relationships, strategic growth and new revenue opportunities.  

 Expedia Group announced a new partnership with PredictHQ, the leading provider of real-world context, integrating its verified event signals and predictive demand intelligence directly into Partner Central, the platform lodging partners use to manage their business. The integration gives lodging partners a clearer view of rising travel demand by combining PredictHQ’s forward-looking demand forecasts with Expedia Group’s rich traveller insights, empowering them to identify, anticipate, and act on demand shifts with greater confidence. New PredictHQ forecasts show traveller spending across accommodation, ground transportation, and food and beverage in North America’s host cities is projected to exceed $8.1 billion USD between June and August 2026, an increase of nearly $750 million over the same period last year.  

As Canadians increasingly look for frictionless, all-in-one travel experiences, Expedia Group’s latest partnership with Uber brings hotel booking directly into the Uber app, making Canada just the second market globally to launch the feature. The integration gives travellers access to Expedia Group’s extensive hotel inventory—ultimately growing to more than 700,000 properties worldwide—while combining accommodation booking, transportation, and loyalty rewards into a single seamless journey, reflecting the growing demand for more connected and convenient travel planning.  

Greater Miami and Miami Beach, Florida – www.miamiandbeaches.com  

Miami Spice Restaurant Months (through Sept. 30) is celebrating its 25th anniversary and inviting travellers to experience specially priced three-course menus at hundreds of restaurants across Greater Miami and Miami Beach. Hispanic Heritage Month (Sept. 15-Oct. 15) celebrates Miami’s multicultural roots with cultural events, performances, exhibitions and community celebrations reflecting the destination’s deep Latin American and Caribbean influences. Miami Carnival (Oct.) is one of Miami’s signature fall celebrations that showcases Caribbean culture through colourful costumes, music, dance and food, highlighting the destination’s vibrant multicultural identity. 

The South Florida Cultural Consortium Exhibition (through Oct. 4) is part of MOCA North Miami’s 30th-anniversary programming. This exhibition showcases contemporary artists from across South Florida and explores themes of identity, heritage and community through a range of artistic mediums. 

Miami Book Fair (Nov. 15-22) is one of the largest literary festivals in the United States and welcomes hundreds of authors, presenters and readers for a citywide celebration of books, culture and ideas. 

Hotel news in Miami includes Delano Miami Beach’s transformation following the South Beach hotel’s extensive renovation. UNFRAMED, Autograph Collection also comes to South Beach with 150-rooms set in a contemporary building with rooftop amenities.  

Kissimmee, Florida – experiencekissimmee.com 

Kissimmee’s Fall lineup includes Crayola Experience’s Screamin’ Green Hauntoween, Gatorland’s Gators, Ghosts & Goblins, and Halloween celebrations at Gaylord Palms and Reunion Resort, making the destination an ideal warm-weather fall getaway.  

Throughout the fall, visitors can experience Central Florida culture through community festivals, seasonal events and the iconic Silver Spurs Rodeo, offering experiences beyond the theme parks. The legendary Silver Spurs Arena is home to one of the nation’s premier rodeo venues. While the signature Silver Spurs Rodeo takes place earlier in the year, fall brings Boots, Bulls & Barrels (Oct. 3), featuring professional bull riding and barrel racing, giving travellers a taste of Central Florida’s rich ranching culture beyond the theme parks. 

Kissimmee continues to strengthen its reputation as a premier sports tourism destination this fall by hosting the NCCAA Division I & II Men’s and Women’s Soccer National Championships at Austin-Tindall Sports Complex, welcoming collegiate athletes and fans from across the country. The championships are part of a multi-year partnership between Experience Kissimmee and the NCCAA, adding to a robust calendar of tournaments and sporting events throughout the season. 

Montréal, Québec – https://www.mtl.org/en  

It’s all about culture this autumn in Montréal. POP Montreal (Sept. 23-27) celebrates its 25th anniversary as one of the city’s best-loved indie music festivals. MAPP_MTL (Sept. 29-Oct. 3) returns to transform Montréal through digital art for its milestone 10th edition, with a program based at Moment Factory and Caserne 26.  MTL à Table (Oct. 29-Nov. 15) is Montréal’s celebrated restaurant week, inviting diners to explore the city’s culinary scene through prix-fixe menus at participating restaurants. This year’s 14th edition builds toward the event’s 15th anniversary in 2027. 

New this fall, Ancestra Lumina brings Moment Factory back to Montréal with its most ambitious project yet: a 2-km nighttime tribute walk through Notre-Dame-des-Neiges Cemetery on the flank of Mount Royal. For something more intimate, the Women in Wine Tour leads small groups through a handful of Montréal wine bars, spotlighting the female sommeliers, bar owners and winemakers driving the city’s natural wine scene. And at Bota Bota, the beloved floating spa in the Old Port, guests can soak in a newly expanded second vessel, the Pavillon, adding fresh decks of pools, saunas and treatment space to the Nordic-inspired experience.   

For sports lovers, UCI Road World Championships Montréal 2026 (Sept. 20–27) is the largest sporting event to come to Montréal since the 1976 Olympics and brings elite cyclists, fan zones and citywide excitement to the destination during peak fall season.  

Oklahoma City, Oklahoma – www.visitokc.com 

From the Oklahoma State Fair and Plaza District Festival to the Oklahoma Regatta Festival, Asian Night Market Festival and Red Earth FallFest, Oklahoma City offers a packed calendar of cultural events throughout September and October. Events include: Oklahoma State Fair (Sept. 17-27), Plaza District Festival (Sept. 26), Oklahoma Regatta Festival (Oct. 2-4), Asian Night Market Festival (Oct. 2-3), Fiestas de las Américas (Oct. 3), Red Earth FallFest Parade & Powwow (Oct. 17) and Braum’s Affair of the Heart (Oct. 23-25). 

The new FAMily Discovery Center opens Sept. 25 at First Americans Museum, providing an immersive, hands-on experience that introduces visitors of all ages to First American cultures and values. The National Cowboy & Western Heritage Museum debuts The Cowboy: An Immersive Journey in November, using multimedia storytelling to explore the history and legacy of the American cowboy. 

Orlando, Florida – www.visitorlando.com 

Among the reasons to visit Orlando this fall is the return of Blue Man Group to a brand-new custom-built theatre at ICON Park, bringing one of the world’s most recognizable live entertainment experiences back to the destination and adding another reason for visitors to explore International Drive beyond the theme parks. Halloween takes over as Orlando embraces fall with weeks of Halloween-themed entertainment, seasonal attractions and family-friendly festivities, making it one of North America’s premier autumn getaway destinations.  

Universal’s highly anticipated Epic Universe remains one of the biggest travel stories of 2026, bringing five immersive worlds, new hotels and a new entertainment district to Orlando. Walt Disney World continues to introduce new entertainment offerings and refreshed guest experiences in 2026, providing fresh reasons for repeat visitors to plan an Orlando getaway.  

EPCOT International Food & Wine Festival (Aug. 27-Nov. 21) is one of Orlando’s most popular annual events that invites visitors to sample global cuisine, specialty beverages and live entertainment throughout EPCOT. Running through November, the festival remains a major draw for food-focused travellers looking to pair culinary experiences with a theme park vacation. FusionFest (end of Nov.) celebrates Orlando’s global cultures. This free multicultural festival brings together cuisine, music, dance, art and traditions from around the world, showcasing the diversity that shapes Orlando.  

San Francisco, California – www.sftravel.com 

The San Francisco Martini Trail now features 25 curated cocktail destinations across the city, including newly added People’s Choice winners Bar Sprezzatura and Fog Harbor Fish House. The trail offers visitors a fun and flavourful way to explore neighbourhoods through one of the city’s most iconic drinks. Fleet Week (Oct. 4-12) returns with ship tours, waterfront events and aerial demonstrations, offering visitors one of the city’s signature annual experiences against the backdrop of San Francisco Bay.  

For culture lovers, Gray Area Festival (Sept. TBD) reflects the city’s creative spirit and brings together artists, technologists and cultural leaders for exhibitions, workshops and performances that explore the intersection of art, technology and society. Hardly Strictly Bluegrass (Oct. 2-4) is one of San Francisco’s most beloved traditions. This free music festival brings acclaimed performers and thousands of music fans together in Golden Gate Park. Yerba Buena Gardens Festival (through Nov. 13) is a long-running free outdoor arts festival that presents more than 100 performances spanning music, dance and cultural programming, adding energy and creativity to downtown San Francisco throughout the season.  

The Hideaway at Hull Bay, St. Thomas, US Virgin Islands – https://hideawayhullbay.com/  

Trade sweaters for swimsuits with a fall getaway to The Hideaway at Hull Bay in St. Thomas. Tucked along the island’s scenic Northside, the private beachfront estate offers an intimate alternative to traditional resorts. Guests can extend summer with sailing, snorkelling, and paddleboarding. Unwind at The Shack, sipping handcrafted cocktails and mocktails infused with fruit grown on the property’s regenerative farm, refreshing coconut water harvested from its coconut trees and traditional bush tea made with herbs grown on-site. Personalized experiences throughout the estate offer an authentic taste of the U.S. Virgin Islands in a secluded, barefoot-luxury setting.  

US Virgin Islands – www.visitusvi.com 

Expected to open in late 2026, The Botany will introduce a new boutique luxury experience to St. Thomas, offering travellers an intimate, design-forward alternative while expanding the island’s upscale accommodations landscape. For sporting and adventure travellers, Wall 2 Wall Sprint Triathlon & Try-A-Tri comes to St. Croix (Sept. 20) with endurance events combining swimming, cycling and running against a backdrop of Caribbean beauty. The USVI Charter Yacht Show at Yacht Haven Grande (Nov. 14-17) brings together luxury yachts, charter brokers and industry professionals for culinary competitions, sailing excursions and networking events that spotlight the territory’s thriving maritime sector. 

National Public Lands Day (Sept. 26) celebrates the natural beauty and ecological importance of public spaces across the U.S. Virgin Islands. On St. John, home to the Virgin Islands National Park, the event offers a timely opportunity to spotlight conservation efforts, outdoor recreation and one of the Caribbean’s most remarkable protected landscapes. Paradise Jam returns to St. Thomas in November, welcoming top NCAA men’s and women’s basketball programs. The tournament combines elite collegiate sports with a warm-weather island escape, making it one of the Caribbean’s most distinctive sporting events. 

Western Massachusetts – www.explorewesternmass.com  

The Big E (Sept. 18-Oct. 4) is New England’s largest fair with agricultural exhibits, live entertainment, regional cuisine and the iconic Avenue of States, drawing visitors from across the Northeast. Brimfield Antique Flea Markets (Sept. 8-13), one of the country’s largest outdoor antiques shows, welcomes thousands of dealers and collectors for one of the world’s premier vintage and collectibles markets.  

For music and culture, Northampton Jazz Festival (Sept. 25-26) celebrates its 15th anniversary with free performances in downtown Northampton. Springfield Museums offers five museums on one campus featuring art, history and science exhibitions, making Springfield one of New England’s premier cultural destinations. And of course, no trip to Western Mass is complete without indulging in fall foliage and river adventures. From whitewater rafting on the Deerfield River to scenic cruises along the Connecticut River, Western Massachusetts pairs vibrant fall foliage with outdoor experiences on the water.