Getaways in Aspen: Events, Festivals, and Luxury Vacation Rentals

Getaways in Aspen: Events, Festivals, and Luxury Vacation Rentals

  • Brittanie Rockhill
  • 05/19/25

Aspen, Colo., transcends its reputation as a world-class ski destination. It is a vibrant mountain town that buzzes year-round with a dynamic calendar of events, captivating festivals, and an unparalleled selection of luxury vacation rentals. Whether you are drawn by the allure of cultural immersion, thrilling sports, or simply a desire for opulent relaxation amidst stunning natural beauty, Aspen offers an unforgettable getaway.

Planning a trip to Aspen involves more than just booking flights; it means aligning your visit with the incredible array of events in Aspen CO or finding the perfect home base that elevates your experience. This guide will help you navigate the rich tapestry of Aspen's offerings, ensuring your visit is tailored to your desires.

Food & Wine Classic in Aspen

June 20-22, 2025

The Food & Wine Classic in Aspen is one of America's premier culinary events, drawing renowned chefs, winemakers, and food enthusiasts from around the globe. This prestigious festival typically takes place in June, transforming Aspen into a three-day gourmet paradise. Attendees can immerse themselves in a world of exquisite tastes and learn from culinary icons.

The Classic features an extensive program of cooking demonstrations, wine and spirits seminars, and panel discussions. The heart of the event is the Grand Tasting Pavilion, where over 150 winemakers, chefs, distillers, and lifestyle brands offer samples of their finest creations. It is an exclusive opportunity to engage with industry leaders and discover new culinary trends.

Aspen Ideas Festival

June 25-July 1, 2025

The Aspen Ideas Festival is a unique event that brings together brilliant leaders, thinkers, artists, and innovators from various fields to discuss the ideas shaping our world. Hosted by the Aspen Institute, this summer festival fosters dialogue and discourse on pressing global issues and future trends.

The festival runs over multiple days, often split into two distinct sections, allowing attendees to choose their focus. Programming includes deep discussions, thought-provoking presentations, and intimate conversations across various topics, from politics and economics to science, technology, and the arts. It is a stimulating environment for those seeking intellectual engagement.

Jazz Aspen Snowmass Labor Day Experience

August 29-31, 2025

The Jazz Aspen Snowmass Labor Day Experience is a renowned outdoor music festival that closes the summer season with a bang. Held at Snowmass Town Park, just a short distance from Aspen, this three-day festival features a diverse lineup of internationally acclaimed artists across various genres, not just jazz.

The setting is spectacular, with the Elk Mountain Range providing a dramatic backdrop to the main stage. Beyond the musical performances, the festival includes the "JAS Village," which offers food and beverage vendors, craft stalls, and kid-friendly activities. It is a lively and inclusive festival in Aspen CO that attracts large crowds eager to enjoy world-class music in a beautiful mountain setting.

X Games Aspen

January 23-25, 2026

X Games Aspen is an exhilarating winter sports spectacle that brings top ski and snowboard athletes to Buttermilk Mountain for intense competition. This event is a significant highlight of the winter calendar, drawing huge crowds and creating an electric atmosphere in the valley.

The X Games feature thrilling competitions in SuperPipe, Slopestyle, and Big Air, showcasing incredible athleticism and gravity-defying tricks. Beyond the sporting events, X Games Aspen often includes live music performances and interactive fan experiences, making it a high-energy festival for action sports enthusiasts. It is an event that truly defines the winter season for many.

Snowmass Balloon Festival

September 12, 2025

The Snowmass Balloon Festival is a captivating spectacle that paints the mountain skies with vibrant colors each fall. This long-standing Rocky Mountain tradition features over 30 festive hot air balloons launching into the air early on Saturday and Sunday mornings. It is a truly picturesque sight.

The festival includes a "Night Glow" on Friday evening, where balloon pilots illuminate their giant balloons under the night sky, creating a magical glow. Spectators gather to watch the launches, and many also enjoy breakfast or brunch at the Snowmass Mall or Base Village afterward. The Snowmass Balloon Festival offers a beautiful and serene experience for all ages.

Aspen Filmfest

TBA 2025

Aspen Filmfest is the premier fall film festival in the region, showcasing a curated selection of films from around the globe. This festival provides a platform for both established and emerging filmmakers, often featuring films that have garnered acclaim at other major international festivals. It is a must-attend for cinephiles.

The festival screens various genres, including documentaries, narratives, and international features, often followed by Q&A sessions with directors and cast members. Aspen Filmfest offers a thoughtful and engaging cinematic experience, allowing attendees to discover new voices and perspectives in film. It is a culturally enriching event in Aspen CO.

Luxury Vacation Rentals

Downtown Aspen Elegance

For those seeking convenience and a vibrant urban experience, luxury vacation rentals in downtown Aspen provide unparalleled access to the town's finest offerings. These properties often range from meticulously renovated historic homes to sleek, contemporary condos, all within walking distance of world-class dining, high-end boutiques, and the Silver Queen Gondola.

Downtown rentals typically boast high-end finishes, gourmet kitchens, and sometimes even private rooftop decks or hot tubs with city or mountain views. Guests staying in these residences can easily stroll to art galleries, enjoy an evening at the Wheeler Opera House, or grab a coffee at a local cafe without needing a car. The allure here is the ability to fully immerse oneself in Aspen's lively atmosphere while enjoying the privacy and amenities of a luxurious home.

Secluded Mountain Estates

For a more private and expansive experience, luxury vacation rentals in the hillsides surrounding Aspen, such as those in the Starwood or Red Mountain areas, offer secluded estates with breathtaking panoramic views. These homes provide a tranquil escape from the bustling town while still being a short drive away from all amenities.

These properties are typically grand in scale, featuring multiple bedrooms, expansive living spaces, and often amenities like private pools, home theaters, wine cellars, and sprawling outdoor entertaining areas. Guests can wake up to stunning vistas of all four ski mountains or the Roaring Fork Valley. These secluded estates provide ultimate privacy and ample space for larger groups or those seeking a truly exclusive mountain retreat.

Work with Brittanie Rockhill for Your Aspen Real Estate Goals

If you're considering buying, selling, or investing in Aspen Snowmass, Brittanie Rockhill brings unmatched expertise and local insight. A Colorado native with a background in international business and real estate, Brittanie has been deeply involved in the Aspen community since 2007. Brittanie’s experience spans nearly $1 billion in sales and includes a thriving rental business that serves second homeowners and investors alike.

Browse our luxury vacation rental properties here. Learn more about price, address, living space, and other features; contact Brittanie Rockhill for a private showing!



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