This classic loop of the Isle of Wight is one for every cyclist’s bucket list.
The joy lies in the roads and scenery: white cliffs, endless beaches, expansive sea views, classic English countryside and pretty villages, all via a network of small, well-surfaced roads with little traffic.
At 109 km with 1,352 m of climbing (or less if you use our route starting and finishing in Cowes – see route notes below), this round the Isle of Wight cycle route is achievable for most. It’s also superbly well signposted (follow the blue and white signs), making navigation a dream. You can ride the route either clockwise (the direction taken in this guide and by the annual Isle of Wight Randonnee) or anti-clockwise.
This route is the undisputed jewel in the crown for road cyclists on the Isle of Wight.
Looking for a loop from Cowes? Here’s a GPX file.
All metrics in this article are approximate.
Though there are some short stretches on main roads, most of this route is on charming, quiet country lanes. These give you a wonderful behind-the-scenes look at the Island away from what you’d see as a tourist in a car.
We particularly love the weather-beaten bleakness of the Military Road in the southwest of the Island. Cycling past the marinas at Yarmouth and Bembridge is also a lovely experience.
Round the Isle of Wight route notes
We were based in Bonchurch/Ventnor (see where we stayed, here), so this ride log reflects that. You can, of course, do the ride from anywhere on the loop. The ferry ports are particularly popular starting points, and you’ll find a GPX download for routes starting from both Ventnor and Cowes in the GPX section, above.
1. Bonchurch to Freshwater: 0-34 km
The ride starts in upmarket Ventnor, but there’s little time to admire the Victorian villas and art deco buildings: your mind is more likely to be focused on the punchy gradients as you head up the cliff.
This Bonchurch to Freshwater section is the hilliest part of the route.
Niton to Blackgang offers up a steep climb and after the summit you dip down, passing Blackgang Chine, England’s oldest theme park (1843). It’s then inland through sleepy, small villages, farms and manor houses on tiny country lanes.
Turning back towards the coast, you hit the impressive bleakness of the Military Road. This takes a westerly course, through the windswept Area of Outstanding Natural Beauty and along the Tennyson Heritage Coast. There are few buildings, and there’s a wild and desolate atmosphere, with the sea to your left and craggy coastline stretching ahead. Prepare yourself for some steep sections too as you climb Compton Down and Afton Down.
2. Freshwater to Yarmouth: 34-38 km
Assuming you’re on a road bike, you’ll probably want to follow our route shown above/in the GPX files.
Otherwise, there is an attractive cycleway that weaves through Freshwater and follows the River Yar estuary along the path of a former railway. As you come into Yarmouth, the reeds, mud beds and watery greyness make way for a marina full of white-sailed boats. We tried this cycle path on a road bike in April; it was just about passable, but not for those fearful of punctures.
3. Yarmouth to East Cowes: 38-64 km
Gradients are pretty kind between Yarmouth and Newtown, and it’s quiet countryside lanes with vibrant hedgerows full of wild flowers and birdsong. The roads start to roll again, and you pass the “town” of Newton (which just consists of National Trust owned Newtown Hall) followed by great views to the yachts on the Solent.
As you come into Gurnard and Cowes, you leave the countryside behind you temporarily. The pancake flat seafront at Gurnard sweeps past pretty beach huts and massive container ships at sea, around the coastline to Cowes. From there you catch the memorable “floating bridge” chain ferry across the River Medina to East Cowes.
4. Cowes to Bembridge: 64-86 km
The north and east of the Isle of Wight are busier than the south and west, but the roads are still pleasant as you head southeast. There’s a short coastal section from St Helens to Bembridge, where you find bobbing boats in the bay.
5. Bembridge to Bonchurch: 86-109 km
You pass Bembridge Windmill (the Island’s only surviving windmill) and weave down narrow lanes back to the south coast.
Turning off the B3395 from Yarbridge and around Wroxall, the lanes are quiet; the narrow country roads are enclosed by hedges and banks which, when we were there, were covered in wildflowers.
The Isle of Wight cycle route round the island is designed to bypass busy roads. This means it avoids the main towns on the Island. However, there are still a good number of places to stop for food and drink along the route. The biggest towns are Cowes, East Cowes, Ventnor and Yarmouth, but Freshwater, Bembridge, Niton and Brightstone also having a range of pubs, cafés and restaurants.
See what you think of these suggestions, all of which are along the route:
- Off the Rails, Station Road, Yarmouth PO41 0QT – en route if you take the gravel cycle way between Freshwater and Yarmouth. It’s in a converted former railway station in a stunning location and right on the bike path (the former railway line) between Yarmouth and Freshwater . The food and coffee are meant to be excellent, but it was so busy when we visited on a sunny bank holiday weekend that we couldn’t even get on the platform! White Cycle Hire also operates out of the former railway building and seemed to be doing a roaring trade when we were there.
- The West Wight Llama Sanctuary, West Mead Main Road, Wellow PO41 0SZ – as well as being a tourist attraction in its own right, the cafe here gets excellent reviews and is a popular stop for cyclists.
- The Best Dressed Crab, Fishermans Wharf, Embankment Road, Bembridge PO35 5NS – fresh, reasonably priced seafood with fantastic views of the harbour.
Popular stops that will serve up hearty cyclists’ fare (but are just slightly off route):
- The Bonchurch Inn, Bonchurch Shute, Ventnor PO38 1NU – a slightly unusual location for Italian restaurant food, but it’s an attractive old pub inside and the food was really good. My favourites were the lemon and crab spaghetti and the lasagne.
- The Spyglass Inn, Ventnor – our children loved this pirate themed pub complete with life-sized pirates and full of memorabilia. Our views on the food were less glowing, but it’s certainly a nice spot for a drink.
- Chale Green Stores, Chale Green, Ventnor PO38 2JN – a well-stocked village store and attached cafe serving delicious cakes.
- Chessell Pottery café, Brook Road, Yarmouth PO41 0UE (between Freshwater and Calbourne)- they serve a mean cream tea (one of the best on the island by all accounts), and lunches too.
- End Of The Line Café, Afton Garden Centre, Afton Road, Freshwater – not smart but hearty food and a nice outdoor seating area.
- PO41, Old Post Office Quay Street, Yarmouth PO41 0PB – it’s not that cyclist friendly since it’s a tiny cafe in the middle of town, but if you’re willing to leave your bike outside, they do a great flat white and an amazing brownie.
- Propellor Inn pub, Sandown Road, Bembridge PO35 5PW – an aircraft-themed pub with hearty pub grub.
If you need an excellent meal at the end of the day, and our staying in/around Ventnor, we can recommend:
- The Ale and Oyster, Esplanade, PO38 1JX – don’t be put off by the name or external appearance of this restaurant; all is not what it seems! The food here is beautifully presented and absolutely delicious: Michelin standards but without the price tag. Go (and ask for a table by the window)!
- Cantina, 20 High Street, Ventnor PO38 1RZ – a small and buzzy restaurant serving modern Italian dishes. Service was good, and the food was yummy. We ate dinner here, but their breakfasts get excellent reviews too.
We stayed for a week in a house in the pretty village of Bonchurch, just outside Ventnor.
If you don’t want to stay in the Bonchurch/Ventnor area then, since this is a loop ride, you could easily stay somewhere else and start the ride from there. Take a look at our Isle of Wight cycling accommodation suggestions.
Read our tips for cycling on the Isle of Wight before you set out.
The least hilly section is from Freshwater Bay to Cowes; the biggest hill is to be found at Chale towards Niton in the anti-clockwise direction.
Each year the Isle of Wight Wayfarer Cycletouring Club organise a ride round the Island on the early May Bank Holiday. Established in 1985, the ride is free (donations requested) and very popular. Enter early if you want to get a place. You can choose between the full loop or a 55km route. The advantage of doing the ride as part of the organised annual randonnee is that there are rest points where you can re-fuel with food and drink, the proceeds of which go to charity. Also, there are six checkpoints, and if you get your card stamped at each, you earn a certificate and can buy a badge. You can start at any point of the route.
Found this guide useful?
- We’d love to hear from you – comment below or drop us a line.
- Don’t miss our other rides on the Isle of Wight: see More Rides below.
- Check out our ultimate guide to cycling Isle of Wight and other articles on the Island, below.
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