Discovering the Thames Path Walk: Henley to Windsor

I recently took a walking holiday in England just outside of London and it was absolutely brilliant.

What made me feel it was perfect was the beautiful blend of scenic beauty, healthy exercise, rich history, and quintessential English charm. A walking tour along the Thames Path walk from Henley to Windsor is a must for those looking for the best of England.

The Route: Following the Thames Path

This 23-mile stretch offers a delightful journey through some of England’s most picturesque countryside, dotted with charming villages, historic landmarks, old churches, and, of course, the iconic River Thames gently guiding you along the way.

This well-marked trail offers an easy walk that is accessible to most fitness levels, winding its way alongside the iconic River Thames. As you follow the path, you’ll pass through charming villages like Hambleden and Cookham, each offering a glimpse into England’s long history and traditional culture.

As you follow the river, you’ll encounter the fascinating engineering marvels of the many locks, where boats gracefully navigate different water levels. The locks, often surrounded by lush greenery and peaceful riverbanks, offer perfect spots to pause, watch the boats pass through, people watch a bit, and take in the tranquil beauty of the Thames.

You can break up this route in two or three days depending on your desired pace. I did this in three days so I could take my time, have drinks along the way, swim in the river, and enjoy more time at the nice hotels.

–> Thames Path Walk Map: Henley to Windsor

Highlights Along the Way

Marlow: Delightful Georgian market town. Marlow’s suspension bridge and the stunning All Saints Church are landmarks not to be missed. The town itself is perfect for a quick coffee break or a leisurely lunch by the river.

Cookham: A village known for its artistic heritage and historic buildings. The Stanley Spencer Gallery, dedicated to the works of the famed British painter, offers a unique cultural stop on your journey.

Cliveden: This grand National Trust property boasts magnificent gardens and woodlands, with breathtaking views over the Thames. It’s a perfect spot for a picnic and a little exploration.

Maidenhead: Cross the river on the historic Maidenhead Railway Bridge, designed by Isambard Kingdom Brunel. The town itself is lively, offering plenty of cafes and shops if you’re in need of refreshments.

Starting Point: Henley-on-Thames

henley on thames

Begin your adventure in the historic town of Henley-on-Thames, famous for its annual Royal Regatta, the famous rowing event established in 1839. This vibrant market town offers the perfect mix of riverside charm and historical intrigue.

Before you start your walk, take some time to explore Henley. The Henley Bridge, St. Mary’s Church, and the Henley River & Rowing Museum are all worth a visit.

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Henley to Danesfield

The 7-mile walk to Danesfield House Hotel and Spa, my stay for the evening, was a gentle introduction to the Thames Path. The river was just gorgeous winding through the serene countryside.

Along the way, I stopped in the little village of Hambleden, where the traditional English cottages made me feel like I had stepped back in time.

By late afternoon, I arrived at the stunning Danesfield House Hotel and Spa. Staying in this grand historic mansion felt like a retreat within a retreat. It was a bit of a splurge, but well worth it if it’s in the budget!

I treated myself to a relaxing spa session and enjoyed the breathtaking views over the Thames Valley before settling in for the night in pure luxury. The next morning I got up and walked around in my robe enjoying a cappuccino and the English countryside.

Danesfield to Cookham

cookham england

After a rejuvenating stay at Danesfield, I set out for the next leg of my journey, heading towards Cookham.

The 6-mile walk was a peaceful escape into nature, with the path taking me through the quiet village of Hurley, where I paused to appreciate the ancient priory nestled by the river. The day’s walk felt almost meditative, with the gentle sounds of the Thames guiding me forward.

A nice stop off along the way is the the Boathouse Restaurant situated right along the riverside with great views, chill vibes, and good selection of drinks and food.

Arriving in Cookham, I checked into The Bel and Dragon, a charming inn that perfectly blended historic character with modern comforts. The inn’s warm atmosphere and the delicious, locally sourced dinner were exactly what I needed after a long day on my feet.

Cookham to Windsor

thames path walk holiday

The final leg of my journey from Cookham to Windsor was the highlight of the walk. Spanning about 10 miles, this stretch offered a perfect blend of natural beauty and gorgeous large houses along the river.

The walk was also mostly shaded, providing a comfortable trek with plenty of inviting spots to stop for a swim or just to take in the views. Which was a good thing too as this was the hottest day of the walk!

Crossing the iconic Maidenhead Railway Bridge was like stepping back in time, with its impressive design by Isambard Kingdom Brunel serving as a reminder of the rich history embedded in this route.

The path through Maidenhead added a unique charm, weaving through the town alongside people’s gardens and behind old pubs. I passed an old church nestled in a field by the river, adding a peaceful, almost timeless feel to the journey.

windsor england

One of the most memorable moments was approaching Windsor from Eton on the opposite bank. Seeing Windsor Castle gradually come into view in the distance was nothing short of epic.

I capped off the day with a well-deserved break at The Boatman’s Pub, a riverside spot with fantastic views, chill vibes, and delicious food.

My journey ended with a stay at the Christopher Wren Hotel, perfectly situated by the river and just a short stroll from the castle. Enjoying dinner with a glass of wine and view of the river was the perfect way to celebrate the end of a great English walking holiday.

Jack Baumann

President of Guidester

Jack Baumann has lived and traveled throughout Europe for over 15 years, creating Guidester in 2014. Over the years Guidester has developed into a unique travel concierge and tour company helping travelers make the most of their trip to Europe.

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