Oakham

If you're walking sections of the route, you'll find Oakham serves as a practical stopping point where the path transitions from the flat fenland terrain into the rolling oolitic limestone landscape that defines the Cotswolds.

The settlement itself is modest, which is genuinely part of what makes it appealing. It's a peaceful place to rest between longer walks, with the surrounding countryside offering plenty of gentle exploration opportunities. The Macmillan Way is fully waymarked throughout, so navigation is straightforward whether you're doing a full day's walk or just a short afternoon stroll through the local footpaths and bridleways.

Many visitors use Oakham as a base for exploring the wider Cotswolds region. Nearby larger towns like Bourne and Market Deeping provide shops and services when you need them. The walking in this area is quite varied—you'll move from flatter sections into proper hill country as you head south along the limestone belt.

The Macmillan Way was established as a fundraising route for Macmillan Cancer Relief, so walking any section contributes to that cause. If you're after a quieter Cotswolds experience away from the busier honey-colored villages, this area delivers exactly that.