Best Winter Running Holidays for 2026 and Beyond

Winter doesn’t mean slowing down! It’s the perfect time to plan a trail running holiday that keeps you active, exploring new trails, and enjoying a change of scenery. From UK escapes in Cornwall to warm-weather adventures in Barcelona, Tenerife, Cyprus, Sri Lanka, and Kenya, our winter running holidays for 2026 and beyond offer scenic trails, guided trips, and multi-day experiences that combine fitness, adventure, and relaxation. Whether you’re a beginner looking for your first guided trail experience or an experienced runner seeking a winter sun escape, these trips are designed to inspire and challenge you.

Contents:

1. UK Winter Escapes

2. Warm-Weather European Winter Running Holidays

3. Exotic Trail Running Retreats

4. Tips for Planning Your Winter Running Holiday

5. Plan Your 2026 and Beyond Winter Running Adventure

1. UK Winter Escapes: Cornwall Trail Running Weekends

For runners looking for a short winter getaway, Cornwall offers scenic coastal trails, rolling hills, and small-group trips perfect for all levels. Spend your days running along rugged coastlines, through quiet villages, and across open countryside, breathing in the fresh sea air. Each multi-day weekend escape is fully guided, combining trail running with relaxation, stunning scenery, and a supportive community of like-minded runners.

Beyond the running, Cornwall provides opportunities to enjoy local cuisine, charming accommodations, and breathtaking coastal views, making these trips a full winter escape experience. With expert guides, you’ll discover hidden trails off the beaten path, ensuring every run feels unique and memorable.

2. Warm-Weather European Winter Running Holidays: Barcelona, Tenerife & Cyprus

For runners wanting to escape the winter chill, Europe offers several sunny winter destinations with trails that inspire both beginners and seasoned runners.

• Barcelona blends urban trails with coastal paths, allowing you to run past historic landmarks, along beaches, and through scenic parks. The city’s mild winter climate makes it ideal for daytime trail runs and exploring cultural highlights off the trails.

• Tenerife is a volcanic playground for trail runners, featuring rugged landscapes, mountain ridges, and panoramic ocean views. Small-group guided trips allow you to safely explore the island’s most beautiful running paths while enjoying sunny winter weather.

• Cyprus combines mountain and coastal trails with ancient villages and stunning scenery. Multi-day trips here offer a mix of trail running, sightseeing, and relaxation, ideal for runners seeking variety and adventure.

All trips are small-group, guided, and multi-day, giving runners the perfect mix of adventure, fitness, and relaxation. These destinations are ideal for anyone looking to stay active in the winter while enjoying a warm-weather escape.

3. Exotic Trail Running Retreats: Sri Lanka & Kenya

For runners seeking adventure, sun, and unforgettable landscapes, Sri Lanka and Kenya provide trail running holidays unlike any other.

• Sri Lanka offers tea plantations, jungle trails, and coastal paths, providing a mix of terrain that challenges and inspires. Guided trips are multi-day adventures, allowing runners to explore the island’s natural beauty, hidden trails, and local culture. The combination of warm winter weather and diverse scenery makes it a bucket-list destination for trail runners.

• Kenya is home to some of the world’s best runners and offers red-earth trails, wildlife encounters, and vast open landscapes. Multi-day guided trips allow you to train like a local, experience safari-style running adventures, and immerse yourself in Kenyan culture. This is the ultimate winter sun running holiday for runners looking for fitness, adventure, and inspiration.

Both destinations are designed for small groups, ensuring a personalized and supportive running experience that caters to all levels.

4. Tips for Planning Your Winter Running Holiday

• Choose a destination that matches your fitness level and trail experience.

• Check group sizes and guided options for safety, support, and a better experience.

• Pack for variable winter weather, even in warmer destinations — layers, hydration, and proper trail shoes are essential.

• Consider multi-day trips for an immersive experience, varied scenery, and structured training.

• Book early for popular winter escapes to ensure availability and secure the best accommodations.

• Think about additional experiences, such as local food, sightseeing, or cultural activities, to make your trip more enriching.

5. Plan Your 2026 and Beyond Winter Running Adventure

Europe and beyond offer the perfect winter running escapes for runners of all levels. From Cornwall weekends to warm-weather trips in Barcelona, Tenerife, Cyprus, Sri Lanka, and Kenya, these guided, multi-day running holidays combine fitness, adventure, and relaxation. With Run Weekends, everything is fully included, accommodation, guided runs, meals, and support, so you can focus entirely on enjoying your running holiday.

Explore upcoming winter running holidays and running retreats for 2026 and beyond with Run Weekends and start planning your next unforgettable trail running adventure today.