With the Isle of Wight Walking Festival celebrating its 25th year (and three of its co-ordinators nominated as Visit England tourism superstars) there’s never been a better time to dust off those route maps and slip into those walking boots again. Plus, with over 500 miles of undulating paths across the Isle of Wight, you won’t be short of options for walks either.

Founded in 1999, the Island’s annual walking festival is said to be one of the biggest (and oldest) in the country. Since its first 5,000 attendees fished out their hiking sticks and set off on an initial programme of 39 walks all those years ago, the Isle of Wight Walking Festival has evolved and expanded enormously, now including historic walking tours, accessible ambles and even hillside speed dating hikes.

Taking place at the same time is the annual Walk the Wight, which sees thousands of people trek from one side of the Island to the other, through ancient forests and over grassy downland, last year raising £460,000 for the Mountbatten Hospice. So, with that, and the walking festival returning for its 25th year (from 11 – 19 May), we’ve decided to share a few of our favourite Isle of Wight routes, from gentle strolls to a few more strenuous options, to get you in the hiking spirit.

Along the River Yar

For the twitchers amongst us, this West Wight route is just the thing. Start outside the quaint Red Lion pub in Freshwater (famous for its parmesan doughnuts with whipped marmite butter), before heading down the twisting road, over the old stone bridge and turning left onto the wide gravelled path.

Isle of Wight Walks - Historic Georgian Tide Mill in Yarmouth
Pause for a while to enjoy the view of Yarmouth’s historic Georgian tide mill.

Once the train line to Yarmouth, walkers along this tranquil stretch of track might be lucky enough to catch glimpses of herons, oystercatchers and even wigeons from between the rustling bulrushes (and to better your chances, bring some binoculars too). After 30 minutes, you’ll reach the historic Georgian tide mill, where you can branch off for a look around Yarmouth town, veer east for a beverage at Off the Rails or continue following the river, before crossing the modern Yar Bridge and heading back to Freshwater on the opposite bank.

Freshwater Bay to the Needles

If you’re looking for something more strenuous (with some literary links too), then set coordinates for Freshwater Bay. After stocking up on provisions at the Orchard Brothers shop (a characterful village retailer, serving locals since 1865), head south towards the sea, passing the thatched church of St. Agnes. Continuing along Gate Lane, until you’ve almost reached the shoreline, signs will point you right, towards the steep grassy paths leading up Tennyson Down.

The thatched church of St. Agnes at Freshwater Bay.
The thatched church of St. Agnes at Freshwater Bay.

This chunky chalk hill takes its name from the famous Victorian poet Alfred, Lord Tennyson, who lived nearby at Farringford and often walked over these downs in his broad-brimmed black hat and cloak. Once you’ve caught your breath at the summit, alongside a granite cross to commemorate the great man, continue west amongst the gorse bushes and heather until you reach Alum Bay and the magnificent Needles rocks.

Isle of Wight Walks - Tennyson Down
Travel in the footsteps of Tennyson on the down that bears his namesake.

Newport to Cowes

For a more family-friendly walk (or cycle), set off from the old brick warehouses down by the quay at Newport, heading past The Bargeman’s Rest, round the corner and onto the cycle path. This three-and-a-half-mile route follows the woody western bank of the River Medina and offers optional stop-offs to see the 1860s timber-clad home of Newport Rowing Club, the medieval church at Northwood and the rows of young grapevines growing at the Pinkmead Estate.

Newport Rowing Club's original wooden boathouse, built in the 1860s, still stands on the banks of the River Medina and is a local landmark.
Newport Rowing Club’s original wooden boathouse, built in the 1860s, still stands on the banks of the River Medina and is a local landmark.

Once you’ve reached the seaside town of Cowes, continue north through the streets of Victorian houses before ending at Northwood House – an elegant neoclassical home dating back to the early 1800s, surrounded by spacious parkland and volunteer-tended gardens.

The Spyglass Inn, perched at the end of Ventnor Esplanade.
If you’re looking for somewhere to rest your weary feet and grab a bite to eat before heading uphill, The Spyglass Inn, perched at the end of Ventnor Esplanade is hard to beat!

Ventnor Coast

If seaside saunters are more your bag, then take one of the stunning coastal routes around Ventnor. From the sparkling waters of the esplanade, you could turn east towards the ancient village of Bonchurch (where Charles Dickens used to come and stay), however, we’d personally recommend a more westerly direction this time around. Begin by climbing the zig-zagging road behind The Spyglass Inn, turn left at The Royal Hotel and slip into the calm and tranquil Ventnor Park, complete with Swiss-style park keeper’s lodge and (at the right time of year) ducklings too.

Isle of Wight Walks - Steephill Cove
Steephill Cove is packed with character.

From here it’s an easy downhill stroll to Steephill Cove, a characterful corner with rustic stone cottages and one of the most popular beaches on the Island. If you’re not finished yet, continue to Ventnor Botanic Garden or keep to the coastal path and you’ll eventually end up in the former smuggling village of Niton.

Ventnor Botanic Garden makes the most of the unique microclimate.
Ventnor Botanic Garden makes the most of the unique microclimate.

Seaview to Ryde

Last on our list (although we’d love to share more) is the smooth and gentle route from Seaview into Ryde – a firm favourite with local dog walkers. Setting off from the centre of Seaview village, head down Bluett Avenue towards the charming row of red-tiled cottages in Salterns Road – some of which date back to the 16th century. Next, turning towards the coast, follow the sea wall to Puckpool Park and past the gun emplacements and fortifications of the old Victorian battery.

Isle of Wight Walks - Seaview
Seaview’s pretty streets, leading to the seafront, are popular with dog walkers.

Once out the other side of the park, it’s a gentle walk past Appley Tower (a 19th-century folly that looks like something Rapunzel might have lived in) on Appley Beach, before reaching the seaside town of Ryde. If all that walking has been thirsty work, then head up the hill and slip into No64 on Cross Street – an atmospheric café housed in a former pharmacy, where barista-made coffees and home-baked cakes await.

For more information on the Isle of Wight Walking Festival and other walks visit isleofwightwalkingfestival.co.uk

Isle of Wight Walks - Appley Tower
Appley Tower is straight out of a fairytale!

Originally produced for Wightlife Magazine