Best Cycling Trails on the Isle of Wight holiday cottages

Best Cycling Trails on the Isle of Wight

The Isle of Wight is a great holiday destination for cyclists of all abilities. Given that the island is reasonably small, it still offers visitors some hilly challenges and a few endurance tests. There’s also lots of scope for fledgling and leisure cyclists to take the country lanes and byways to enjoy some mild and easy-going routes along the coast. We have compiled a few trails for you to try out on your next visit to this alternatively rugged and rural holiday destination.

Brighstone Circular (Brighstone – The Tennyson Trail – Shorwell – Brighstone)

  • 10 miles – moderate

2 bikers

Sporadically hilly, this trail affords you some spectacular views across the English Channel, in one of the best pockets of unspoilt countryside on the island. The southern and western ends of the island offers some large stretches of uncommon chalk grasslands and big sky country. If you love open spaces this trail is for you.

Brighstone has a pleasant grocery store to stock up with some eats for a grand picnic. The High Downs/Tennyson Downs are the former haunting grounds of the once Poet Laureate, Alfred Lord Tennyson. He lived close to Brighstone and his memorial, a large stone cross can be seen along the trail.  As the route arrives close to Shorwell, you could stop for a cold drink at the village’s Crown Inn. You may need it to make the climb up the hill back to Brighstone.

Ryde Circular (Ryde – Upton – Brading – Alverstone – Newchurch – Upton – Ryde)

  • 15 miles – moderate

sunset biker

Varied terrains and a string of traditional Isle of Wight villages are the reason for embarking on this inland cycle trail - originating and concluding in the seaside resort of Ryde. Ryde is a superb base for shopping, exploring, and evening entertainment. It also has some wide beaches, especially on the eastern side of  town.

As you go inland, the route meanders through the village of Upton, then Brading which is famous for its Roman villa. There are several options for a fine lunch at one of the pubs in Newchurch, or at the Garlic Farm a short distance further on along the trail. The journey is hilly along some stretches and affords some great views of the coast in the distance to the east.

Freshwater Circular (Freshwater - Yarmouth - Totland - Alum Bay - Freshwater)

  • 10 miles – easy to moderate

the downs

This signposted route meanders through the small towns and villages found at the western end of the Isle of Wight.  Originating in Freshwater Bay, the trail winds north past Freshwater town via the cycle path and ends at Yarmouth. Yarmouth is home to an impressive castle built by Henry VIII, Fort Victoria Country Park, and a lovely selection of boutique shops selling a variety of gifts, jewellery and local produce. You may also want to stop in at one or two of Yarmouth’s pubs and restaurants where you can sample some of the excellent seafood on offer.

After spending some time in Yarmouth, the route heads south along the coast to Totland and Totland Bay, where there is a beautiful beach, and finally towards Alum Bay with its staggering views of the Needles and The Solent.  This route offers many opportunities for detours and it is worth taking the time to see the Old and New Batteries up above Alum Bay and the Tennyson Monument.

Back at Freshwater Bay, there is a teashop and lifeboat charity shop from where you can buy ice creams. Freshwater Bay is also popular with swimmers, so you might like a refreshing swim to cool down after your cycle ride.

Newport Circular (Newport - Cowes - Whippingham – Newport)

  • 10 miles – easy

cowes marina

This is a pleasant, level waterside route from Newport to Cowes up the west bank of the River Medina and back south along its eastern bank. This section is also a part of the Sustrans National Cycle Route 23. It lets you visit Cowes, with its boating history and colourful waterfront area full of small boats and the moored launches at Cowes Yacht Haven.  

You can stop and take in the surroundings as you make the short journey across the Medina on the floating bridge (chain ferry) so that you can begin the second leg of the ride back south to Newport from East Cowes. The village of Whippingham is home to the very distinctive St Mildred’s Church, partially designed by Prince Albert. It is well worth disembarking for a closer look and potential photo opportunity.  The countryside is lush and green in this area as the land opens out beyond Whippingham.

Your path cleaves close to the fields where the gigantic Isle of Wight Festival takes place every year. Newport has a number of shops for buying supplies and is also a good place to get your bike fixed or tuned by the people at the Wight Mountain Bike Shop

Sandown Circular (Sandown – Yaverland – Brading – Sandown)

  • 5 miles – easy


This is a lovely proposition for those looking for a leisurely option that takes in the best of the east side of the island. Beginning and ending at Sandown train station, this trail runs along the esplanade northwards, with sunny sea views of the Solent and the south coast of England visible on your right-hand side. Then you hit Yaverland, a lovely village characteristic of many Isle of Wight, countryside villages. Also see Brading, which is also a stop on the Ryde Circular.

The circuit then drops inland back through to Sandown. You could also return the same way you came, back along Sandown’s esplanade. There are many places in town to enjoy some well-deserved refreshments. Why not treat yourself to a Minghella ice cream cone?

Military Road (Niton – Blackgang Chine – Compton Bay – Freshwater Bay – Niton)

  • 8 miles - moderate

The Military Road has been voted one of the best drives in Europe, at sunset it’s easy to see why. Cycle west along with wide road between Niton and Freshwater for some of the best big sky and deep blue sea views in the south of England. The Military Road will remind visitors of some of the outer lying highways in California, Cape Town, West Australia and the west coast of South Island in New Zealand.

There are some excellent vistas of Compton Bay, and you also skirt some gorgeous chalk grasslands, home to orchids and butterflies in the warmer months. A fast spin along the route can be an invigorating experience, as it is a long gradual descent for a large stretch of the road going westwards. There are shops and pubs for refreshment and replenishment at the Freshwater end of the trail. Because of cliff erosion the road is occasionally closed for maintenance, so check local press before you set off.

A cycling holiday on the Isle of Wight

We have some lovely cottages across the island, many with storage space for bicycles. Take a look at our collection of Isle of Wight accommodation to inspire your break away.  

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