Daily Itinerary

Day 1 Fri, Sep 20 49 km · 1h 25min · 6 stops
1
Uppingham Start Point Start

The starting point for your Midlands adventure, a charming market town in Rutland.

2
Wing Maze Stop

A unique, ancient turf maze, one of only eight surviving in England, offering a moment of quiet contemplation and a bit of a puzzle.

2.5 km · 5min from Uppingham Start Point
3
Rutland Water Scenic Drive Viewpoint

A scenic loop around the Hambleton Peninsula of Rutland Water, offering stunning views of the reservoir and surrounding countryside.

8.0 km · 15min from Wing Maze
4
Oakham Castle Stop

Visit the oldest great hall in England, famous for its collection of ornate horseshoes presented by royalty and nobility over centuries.

10 km · 20min from Rutland Water Scenic Drive
5
Mallard Pass Vineyard Stop

Enjoy a taste of local English wine at this charming vineyard, perhaps a tasting or a stroll among the vines.

18 km · 30min from Oakham Castle
6
Stamford (Evening Jazz/Wine) Destination

A historic Georgian market town, perfect for an evening of local cuisine and a chance to find a cozy spot with live music or fine wine. Explore the pubs and wine bars for a relaxing end to the day.

10 km · 15min from Mallard Pass Vineyard
Day 2 Sat, Sep 21 82 km · 2h 5min · 6 stops
1
Stamford Start Point Start

Begin your day from the beautiful Georgian town of Stamford, heading towards more historical and natural wonders.

2
Burghley House Stop

Visit one of England's greatest Elizabethan houses, with stunning architecture, gardens, and deer park.

2.0 km · 5min from Stamford Start Point
3
Barnwell Country Park Stop

A beautiful country park along the River Nene, perfect for a peaceful walk, birdwatching, and a breath of fresh air.

20 km · 30min from Burghley House
4
Welland Valley Vineyard Stop

Discover another local English vineyard, offering a chance to sample regional wines and enjoy the rural setting.

30 km · 45min from Barnwell Country Park
5
Foxton Locks Viewpoint

A truly unique sight, the longest flight of staircase locks on the English canal system. Watch barges navigate this engineering marvel.

10 km · 15min from Welland Valley Vineyard
6
Leicester (The Musician) Destination

Arrive in Leicester, a vibrant city with a thriving music scene. The Musician is a renowned venue for live jazz, blues, and folk music, perfect for fulfilling the trip's theme.

20 km · 30min from Foxton Locks
Day 3 Sun, Sep 22 59 km · 1h 35min · 5 stops
1
Leicester Start Point Start

Depart from Leicester, ready for a scenic ride back towards Uppingham, enjoying the final leg of your journey.

2
Bradgate Park (Old John Tower) Stop

Explore this historic deer park, home to wild deer and the ruins of Bradgate House, with Old John Tower offering panoramic views.

12 km · 20min from Leicester Start Point
3
Melton Mowbray (Pork Pies) Food

Stop in Melton Mowbray, the rural capital of food, famous for its Stilton cheese and, of course, the authentic Melton Mowbray pork pie. Grab one for lunch!

15 km · 25min from Bradgate Park (Old John Tower)
4
Manor Oak Vineyard Stop

A final opportunity to visit a local vineyard, perhaps pick up a bottle as a souvenir of your trip.

20 km · 30min from Melton Mowbray (Pork Pies)
5
Uppingham Return Point Destination

The end of your journey, returning to charming Uppingham with memories of scenic rides, fine wines, and jazz.

12 km · 20min from Manor Oak Vineyard