Trail of the unexpected: Pedal power on the Isle of Wight

The island may be small, but it has plenty of serious climbs for cyclists, says Simon Usborne

My advice if you were thinking about a cycling holiday to the Isle of Wight (you should – it's great): the seaside town of Ventnor is not the place to stay unless you have (a) a car, preferably one in good condition, or (b) the physique of Bradley Wiggins. Rarely have I encountered roads as precipitous as those leading inland from the town on the island's south coast.

I had arrived with my girlfriend, Jess, with limbs of varying fitness and scant knowledge of the topography, which is persistently lumpy across the 20-mile-wide chunk of land off Hampshire. But, as we would discover, rewards await those willing to get out of the saddle.

And islanders would like you to get on your bike, keen as they are to capture some of the cycling boom heard of so much on the mainland. I had been invited to ride in the Wight Riviera Sportive, a new addition to Britain's increasingly crowded calendar of timed mass rides. Two more have sprung up in the past year, including the Wiggle Wight Ferry Sportive, which includes a boat ride from its start on the mainland. Next weekend sees the return of the week-long Isle of Wight Cycling Festival (22-30 September) of more than 50 organised rides and events for on- and off-road cyclists.

The day before my 72-mile ride, we road-tested the island as a destination for cyclists who might prioritise lunch over Lycra and calming sea views over lung-busting climbs. It began with possibly the world's greatest porridge. Ventnor is an old Victorian resort once beloved of the poet John Betjeman, who admired its "gardens of palms, myrtles and hydrangeas and its glimpses of the sea". It is gaining in popularity today as a quaint bucket-and-spade resort happily free of the gloss and pretension of, say, some of its Cornish rivals.

The Hambrough, a small hotel perched high above the front, has some of the best of Betjeman's glimpses, as well as one of the finest kitchens on the island. (It deserves its Michelin star for the porridge alone.) We followed breakfast with a lazy morning spent mainly on deck chairs before packing my bike in the car and driving winding roads in search of lunch.

The Garlic Farm is perhaps the only tourist attraction devoted to an allium. It produces more varieties of garlic than you thought existed, including one the size of a grapefruit, and entertains visitors with exhibits, a farm shop and, most crucially, a restaurant, where we ate, among other things, delicious deep-fried garlic scapes (the stalky bits).

From there we motored west to Yarmouth to pick up Jess's rented bike from Wight Cycle Hire. Our mission: to pedal west to the Needles, a series of striking if un-needle-like chalk stacks that rise from the sea to the west of the island. Six miles shouldn't be too much of a challenge but with one less-seasoned cyclist on a clunky rental bike on country lanes that were rather hillier than we'd expected, it took us more than an hour. If you're a pootling cyclist anywhere on the island, limit yourself to short distances.

We wound on past the touristy Needles theme park up the headland to a spooky military rocket-testing station left to crumble since the Sixties, which gives views of the stacks themselves. They are not the most dramatic natural wonder but worth gazing at in the late afternoon with the sun coming through the clouds.

Once back at Ventnor and fully restored, we took the fancy option of the Hambrough's tasting menu (the highlight: mullet with samphire, rosemary dumplings and oysters). Then early to bed for me before the big ride.

After a brass-band send-off, the route began for 500 riders with 25 miles along roads closed to traffic, a rare treat for cyclists. The course then split, allowing those who'd signed up for more a tour of much of the western half of the island. (Those with more time and legs ventured further out along the full, 95-mile route.) We shared the roads with traffic, but it rarely amounts to much outside the peak summer season.

I felt strong until the exposed coastal Military Road, which links the south and west tips of the diamond-shaped island. Along with the hills, a headwind sapped my energy, until a turn back inland appeared to offer some relief – before cruelly leading to one of the steepest climbs on the course, along Lynch Lane.

I'd been riding fast until now, sticking with guys much fitter than me, but, alone for the last 15 miles or so, every pedal stroke became a grind and I crawled into Yarmouth (after a respectable four hours and 12 minutes) to receive my free, restorative tub of local Minghella's ice cream. What we had seen of the Isle of Wight in two days made us vow to return. With the bikes? Sure, but we'll be training for those hills first.

Travel essentials

Getting there

Simon Usborne travelled with Red Funnel (0844 844 998; redfunnel.co.uk), from Southampton. It Two nights' B&B at The Hambrough (01983 856 333; robert-thompson.com), with dinner costs £228pp.

Other connections are by Wightlink (0871 376 1000; wightlink.co.uk) and Hovertravel (08434 87 88 87; hovertravel.co.uk)

Bike hire and more information

Wight Cycle (01983 761800; wightcyclehire.co.uk)

CycleWight.co.uk