Challenge walks in Scotland in September 2025
Find challenge walks near me in Scotland in September 2025 - search by date or place, display on a map or use the advanced search to find your perfect race.
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Click an event for full event details, location, route, sustainability, what's included and how to enter.

- Sat 13 Sep
- £20
- Sat 13 Sep
- £20
Follow the Seagulls | Scotland | One Day Challenge
A trekking challenge with tranquil forests, historic castles, quaint fishing villages and beautiful beaches to support brainstrust, the brain cancer charity.
- Enter online
- Fundraising required
- Undulating
- Age 18 & over
- 26 miles walking

- Sat 13 - Sun 14 Sep
- £30
- Sat 13 - Sun 14 Sep
- £30
Follow the Seagulls | Scotland | Two Day Challenge
A trekking challenge with tranquil forests, historic castles, quaint fishing villages and beautiful beaches to support brainstrust, the brain cancer charity.
- Enter online
- Fundraising required
- Undulating
- Age 18 & over
- 50 miles walking

- Sun 14 Sep
- 6 charities
- Sun 14 Sep
- 6 charities
The Kiltwalk Edinburgh | Mighty Stride
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Scotland's capital this year over a challenging 21 mile route.
- Enter online
- Fundraising required
- Undulating
- Age 13 & over
- 21 miles walking

- Sun 14 Sep
- 5 charities
- Sun 14 Sep
- 5 charities
The Kiltwalk Edinburgh | Big Stroll
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Scotland's capital this year over an achievable 11 mile route.
- Enter online
- Fundraising required
- Undulating
- Age 10 & over
- 11 miles walking