Freerein Riding HolidaysBlogFeatured5 Tips To Maximise Your 2026 Holidays for Your Dream Riding Trip

5 Tips To Maximise Your 2026 Holidays for Your Dream Riding Trip

September 23, 2025/adele/, , ,
horse-riding-holidays-old-drovers-2-1 1

Planning your 2026 diary now might feel early—but if you’re dreaming of cantering through the Welsh hills or meandering along quiet forest tracks, the smartest riders book well in advance.

By syncing annual leave with UK bank holidays, you can stretch your time off and secure the very best trail dates during our next season, which opens on May 1st 2026!

1. Snap Up the Key UK Bank Holiday Weeks

Here’s how 2026 falls for England & Wales (check local variations if you’re in Scotland or Northern Ireland):

  • Early May Bank Holiday: Monday 4 May – perfect for a 3-day spring trail like the Silver John Trail booked with Hiring Your Own Guide for a bespoke experience as the hills turn green, or join our guided 4-day Welsh Prince Trail that departs on 1st May, you only need to take that Friday off!

  • Spring Bank Holiday: Monday 25 May – ride into late-spring wildflowers with only four extra leave days for nine days off! Our Self-Guided trips, like our 7-day Radnor Ronda trail, offer all the flexibility to pick your own dates, duration, and to enjoy a true trail riding adventure on your own terms.

  • Summer Bank Holiday: Monday 31 August – ideal for warm, long daylight rides. Make it a trip to the beach for a riding-meets-swimming holiday with our Border To Coast flagship 6-day trail. Hire your own guide, pick your own dates and riding companions, and off you go for a riding holiday you’re sure to remember for a long time!

(Tip: Scotland and Northern Ireland differ slightly—double-check your region.)

2. Layer Annual Leave Around the Holidays

Pairing a single week of annual leave with bank holidays can turn five days of holiday allowance into nine or ten days in the saddle.

  • Book Monday–Friday around the late May bank holiday for a generous spring escape.

  • Add a Friday or Tuesday to the August bank holiday to create a relaxed end-of-summer trail.

3. Reserve Your Favourite Trail Early

The most popular Freerein adventures—like the Border To Coast or Welsh Prince Trail—sell out months ahead. By securing your 2026 dates now you’ll:

  • Choose Your Horse: returning Freerein riders can often request their favourite mount!

  • Guarantee Ideal Weather: whether you want crisp spring air or balmy late-summer evenings, booking early ensures the right season.

  • Spread Costs: you’ll pay a 20% deposit when you book, and the balance is due 8 weeks before your depart date, so that you don’t have to cash out the whole amount in one go. Booking early also lets you plan your travel to the stables at the best rates.

4. Consider a Self-Guided or Bespoke Experience

Early planners also get the pick of our Self-Guided Trails or the exclusive Hire Your Own Guide option. These fill fast because they give you complete freedom over start date, pace and group size.

5. Make It a Group Adventure

If you’re riding with friends or family, aligning everyone’s calendars can be tricky. Locking in those 2026 dates now avoids last-minute stress—and helps your travel companions request time off while availability is wide open.

Ready to Ride?

The 2025 season is nearly booked out. Get ahead for 2026, combine your annual leave with bank holidays, and make your dream riding holiday a reality with Freerein Riding Holidays!

👉 Explore 2026 Riding Holidays

Any planning questions?

Email us at trails@freerein.co.uk or visit our Freerein Trail Finder and we’ll be happy to help!

adele