Refine your search for walks in Old Windsor
Old Windsor walks
Englefield Green to Walton-on-Thames
Visorando Member
13.35 mi
+141 ft
-318 ft
6h 15
Moderate
Departure from Borough of Runnymede (Surrey)
This section of our walk starts at Englefield Green. It is 13.35 miles long and takes in Englefield Green, Runnymede Memorials, Egham, The Causeway, Staines Riverside, the Thames Path, Laleham, Chertsey Bridge, Shepperton Riverside, Shepperton Ferry, Desborough Cut, Walton Bridge and Walton-on-Thames.
Runnymede
2.17 mi
+210 ft
-223 ft
1h 10
Moderate
Departure from Borough of Runnymede (Surrey)
Visit of Runnymede National Trust to see the Magna Carta monument. Dog friendly walk.
Windsor Castle to Chequers
27.64 mi
+1,280 ft
-1,076 ft
3 days
Moderate
Departure from Royal Borough of Windsor and Maidenhead
In September 2025, the President of the United States of America made a state visit to Britain, staying at Windsor Castle as guest of the King, then travelling to meet the Prime Minister at Chequers, the official country residence.
It’s 20 miles as the helicopter flies from Windsor to Chequers; this is a 25 miles walking route between the two.
Windsor to Bourne End
11.25 mi
+43 ft
-79 ft
5h 15
Moderate
Departure from Royal Borough of Windsor and Maidenhead
The first stage starts at Windsor Castle, passing over the River Thames to Eton, then follows the Jubilee River to near Maidenhead, where it picks up the Thames Path national trail to Bourne End.
At this point, continue on stage two to High Wycombe.Alternatively, there is a regular bus service (37) back to Windsor, or take the train to Maidenhead for Great Western and Elizabeth Line services.
Thames Valley
125.34 mi
+5,676 ft
-5,722 ft
9 days
Easy
Departure from Royal Borough of Windsor and Maidenhead
This circular long distance path has access points that are easily reached by train from London, Reading and adjoining stations. If time is limited it can be walked in sections at weekends and bank holidays with one or two overnight stops.
The walk passes through a variety of beautiful countryside including river valleys, chalk downland, coniferous forests, rare heath, and beech woods that are carpeted with bluebells in spring.
Windsor to Sandhurst, Thames Valley
17.14 mi
+646 ft
-518 ft
8h 25
Moderate
Departure from Royal Borough of Windsor and Maidenhead
The 1rst sections of this walk follow The Three Castles Path, a long distance route inspired by the 13th century journeys undertaken by King John between his castles at Windsor, Odiham and Winchester
Windsor & Eton Riverside Station to Bourne End
11.10 mi
+39 ft
-23 ft
5h 10
Moderate
Departure from Royal Borough of Windsor and Maidenhead
The route follows the Thames Path all the way. At times the path can be narrow, so be aware. The route crosses Windsor Bridge to Eton, then turns left to follow the Thames Path past Boveney, Dorney Lake. Oakley Court and Bray Studios are soon visible across the river. Next is Bray Lock, then through Maidenhead, and Cookham to Bourne End.
Windsor & Eton Riverside to Englefield Green
11.42 mi
+394 ft
-230 ft
5h 35
Moderate
Departure from Royal Borough of Windsor and Maidenhead
This section of our walk starts is 11.4 miles. It starts at Windsor & Eton Riverside Station and takes in Windsor Castle, The Long Walk, Windsor Great Park, Three Castles Path, Virginia Water, Valley Gardens, Savill Garden and Englefield Green.
Datchet Station to Windsor & Eton Riverside
14.75 mi
+33 ft
-33 ft
6h 50
Moderate
Departure from Datchet (Royal Borough of Windsor and Maidenhead)
This section of our walk starts at Datchet Railway Station. It is 14.75 miles and takes in Datchet Village, the Jubilee River, Dorney, Maidenhead Riverside, Dorney Lake, Boveney, the Thames Path, Eton High Street and Windsor Bridge. It is the longest of the five sections, but is flat and easy to follow.
The Freedom Trail
63.80 mi
+623 ft
-659 ft
5 days
Moderate
Departure from Wraysbury (Royal Borough of Windsor and Maidenhead)
The Freedom Trail is a long distance path, designed to link places associated with these and other events in our history, and how they would form a blue-print for the world we know today. I'm not really an historian or a walker, but through a few other projects I have been involved with, I thought this would be something interesting to do. The path is 64 miles long.
Wraysbury Station to Datchet Station
13.16 mi
+20 ft
-13 ft
6h 05
Moderate
Departure from Wraysbury (Royal Borough of Windsor and Maidenhead)
The first section of the walk starts at Wraysbury station. It is 13.15 miles and takes in Wraysbury, Ankerwycke, Church Lammas, St Mary's Church, Duncroft Manor, Staines Moor, central Staines-upon-Thames, Staines riverside, The Hythe, Thames Path, Runnymede, Old Windsor and Datchet.
Around Reading
107.08 mi
+2,956 ft
-3,402 ft
15 days
Easy
Departure from Sunninghill and Ascot (Royal Borough of Windsor and Maidenhead)
This is a 16 stages walk around Reading accessible from one railway station to another.
Start & End: Martin's Heron Railway Station (RG12 9TZ) Grid ref. SU 887 683
Ascot to Windsor, around Reading
7.60 mi
+262 ft
-351 ft
3h 45
Moderate
Departure from Sunninghill and Ascot (Royal Borough of Windsor and Maidenhead)
An interesting walk on good paths following the route of the royal procession from Ascot through Windsor Great Park and offering a 'surprise' view of Windsor Castle.
Dorney and the Thames on Film
Association / Club / Walk leader5.23 mi
+20 ft
-20 ft
2h 25
Easy
Departure from Dorney (Buckinghamshire)
This route will take you to see historic buildings, modern engineering projects and film locations, before finishing with a stroll along the peaceful and tranquil Thames.
Staines-upon-Thames to Windsor & Eton Riverside Station
10.54 mi
+338 ft
-312 ft
5h 10
Moderate
Departure from Borough of Spelthorne (Surrey)
Mostly towpath and parkland, there is a lot to see on this stage, so start early. The route crosses Staines Bridge, then follows the Thames before crossing the road at Runnymede.
Martin's Heron to Ascot, around Reading
4.34 mi
+95 ft
-115 ft
2h 05
Easy
Departure from Winkfield (Royal Borough of Windsor and Maidenhead)
A level walk through Swinley Park, part of the Crown Estate, then across Ascot Heath with a close-up view of the world-famous race course.
Maidenhead to Windsor, around Reading
6.59 mi
+26 ft
-26 ft
3h 05
Moderate
Departure from Royal Borough of Windsor and Maidenhead
Follow the Thames Path through the lovely scenery of Cliveden Reach. Visit Boulter's lock, enjoy the wildlife on the newly-created Jubilee River and pass close to Eton College.
Black Park Family Circular
3.19 mi
+59 ft
-66 ft
1h 30
Easy
Departure from Wexham (Buckinghamshire)
Black Park is a great place for a family outing. This short walk passes through lovely woodland and open heathland. You will also pass Pinewood Studios. Leave enough time to relax at the café or have a picnic by the lake.
More walks in Old Windsor
Discover also walks in surrounding cities: