From coast to coast, and even high in the Rockies, this summer’s most elevated events and festivals offer an enticing blend of culinary mastery, refined design, and luxurious experiences. Whether you’re toasting rare vintages in Napa, celebrating high-fashion-inspired rooftop pool designs in Dallas, or mingling with top chefs in Aspen, discover 10 of the best Summer events and festivals designed for discerning travelers and tastemakers.
Carmel Culinary Week – Carmel-by-the-Sea, CA
May 30 – June 7, 2025
Set in one of California’s most enchanting seaside towns, Carmel Culinary Week invites you to immerse yourself in a vibrant celebration of food, wine, and community. This charming, one-square-mile village transforms into a gourmet playground with chef showdowns, pop-up dining experiences, elegant coastal soirées, and immersive culinary events. From al fresco dinners on historic Dolores Street to lively competitions in Devendorf Park, it’s a flavorful way to welcome summer on the majestic Monterey Peninsula.
James Beard Awards – Chicago, IL
June 16, 2025
Known as the “Oscars of the food world,” the James Beard Awards return to Chicago to honor excellence across the culinary and food media industries. The prestigious Restaurant & Chef Awards take place at the Lyric Opera, featuring glamorous red carpet arrivals and a post-event walk-around tasting at Union Station. For the ultimate VIP experience, you can indulge in a multi-course dinner curated by James Beard Award-winning chefs Michael Rafidi and Suzanne Goin. It’s an unforgettable night celebrating the best in American gastronomy.
Food & Wine Classic in Aspen – Aspen, CO
June 20–22, 2025
The Food & Wine Classic in Aspen remains one of the country’s most iconic culinary festivals, and for good reason. This year’s edition boasts 70+ celebrity chefs and beverage experts, over 40 decadent tastings and seminars, and three indulgent days of world-class cuisine and wine. Set at the base of the Colorado Rockies, the event’s legendary Grand Tastings Pavilion and intimate culinary experiences make it a must for epicureans seeking mountain luxury.
Design Weekend with Ariel Okin – Mayflower Inn & Spa, CT
June 21–22, 2025
Escape to the idyllic Connecticut countryside for a weekend of elevated design at the Mayflower Inn & Spa, Auberge Resorts Collection. Curated by interior designer Ariel Okin and her editorial brand Fenimore Lane, the stylish event includes an all-day Design Bazaar and a summit of engaging and educational panels and workshops led by renowned designers and tastemakers. It’s a chic, serene gathering for design lovers and style-minded travelers alike.
Missoni Rooftop Pool Pop-Up – Hôtel Swexan, Dallas, TX
Launching in June 2025, all summer
Fashion meets leisure at Hôtel Swexan’s rooftop pool pop-up in collaboration with iconic Italian fashion house Missoni. This summer-long experience transforms the Dallas skyline with Missoni’s signature stripes, custom cabanas, branded loungers, and a stylish cocktail and bites menu. You can choose between the classic Missoni Experience package or the ultra-luxe La Vita Missoni suite stay for the ultimate poolside escape infused with high fashion.
The Hill in New York – Brooklyn, NY
July 11–13, 2025
If you’re a tennis fan, then you’ll be enthralled to learn that Wimbledon is coming stateside this summer at The Hill in New York, a stylish outdoor activation hosted at Emily Warren Roebling Plaza in DUMBO. Featuring big-screen live matches, quintessential British fare, luxury brand activations, and live performances by British pop stars, this multi-day event brings sporty sophistication to Brooklyn. It’s a fashionable celebration of tennis, culture, and summer in the city.
Taste of Napa & Festival Napa Valley – Napa, CA
July 12, 2025
Part of Festival Napa Valley’s summer season, Taste of Napa is a signature tasting event that brings together over 90 wineries, restaurants, and culinary artisans at The Meritage Resort. With live jazz performances, interactive games, and two tiers of ticketed experiences (including the exclusive Reserve Tasting Salon), this indulgent afternoon offers the perfect pairing of fine wine and food in one of California’s most celebrated destinations.
Heritage Fire – Snowmass Village, CO
August 2, 2025
Experience whole-animal cookery at its finest at Heritage Fire, the open-air culinary spectacle returning to Snowmass Base Village. Set against the stunning Rocky Mountains, this live-fire event features celebrated chefs grilling heritage-breed meats en plein air, complemented by free-flowing wine, spirits, and globally inspired bites. It’s a celebration of sustainability, flavor, and fire in one of Colorado’s most luxurious alpine settings.
Vail Wine Classic – Vail, CO
August 7–10, 2025
Sip and savor at elevation during the Vail Wine Classic, a premier wine festival offering a series of immersive experiences, from grand tastings with 100+ wineries to sunset showcases of 90+ point wines and sommelier-led pairing dinners. Surrounded by the beauty of the Colorado Rockies, this event is tailor-made for oenophiles who appreciate adventure and refinement in equal measure.
Breckenridge Wine Classic – Breckenridge, CO
August 21–23, 2025
Rounding out the season is the Breckenridge Wine Classic, a high-altitude celebration of food, wine, and alpine adventure. From scenic sommelier-guided hikes and intimate lunches to a showstopping Grand Tasting at 9,600 feet, this three-day event offers an elevated experience in every sense. Perfect for wine lovers with a taste for the outdoors and a flair for the refined.
Whether you’re planning a weekend escape or a cross-country adventure, these elevated summer events promise unforgettable moments filled with flavor, style, and inspiration. From iconic wine festivals in dreamy destinations to design retreats in the countryside and fashion-forward rooftop pop-ups, there’s no shortage of extraordinary experiences to enjoy this season.
Ready to discover even more luxurious places to visit and activities to enjoy? Explore the Travel section on Inspirations & Celebrations for insider guides, hotel reviews, and dream-worthy itineraries designed for the sophisticated traveler.
[Images c/o featured events.]
