please empty your brain below

I have fond memories of Pymmes Brook in Arnos Park. Arriving with a friend on our bikes, we would proceed along the river bank, making our way under each of the many footbridges which span the river. It sounds odd now, but we found it tremendous fun.
And the longest underground walk in a tube station?

That seems like another category to add.
There may be an opportunity to walk underneath a bit of Tramlink along the elevated section in Waddon New Road. Based on Google Maps there seems to be a stretch where the fencing is in undergrowth adjacent to the pavement.

There also appear to be trivial short stretches underneath each end of the Dangleway.
The pedestrian tunnel under Exhibition Road seemed quite long when I was a child.

dg writes: 400m approx
You can walk under Wharncliffe Viaduct which may be a contender. Bring wellington boots.
You can physically walk under the railway viaducts around Southwark but it’s all private property. The longest stretch is between Great Suffolk Street and Ewer Street. There’s various businesss that use the space and there used be a night club at the Great Suffolk St end that took up considerable space.
Thd DLR the most viaducty of all London's railways? Maybe by miles, but by proprtion the original London & Greenwich Railway must be a contender, as it was built entirely on viaduct.

You can't walk under it all the way though. It was originally built with a pedestrian walkway alongside.
Leake St under Waterloo Station must be a contender for something here.

Longest named street under something maybe?
In the Rotherhithe Tunnel image, on my first glance, the upside down '20' speed marker read as 'DG'.
Tenuous, I know, but you could do a circuit of the Barbican Estate (and adjoining spaces) at podium level while being underneath something (even if it's just a canopy) pretty much all the time.

Starting, say, at the top of the steps underneath Defoe House and walking anticlockwise, round Lauderdale Tower, then continuing down towards the (ex) Museum Of London), then along London Wall, and round via the newer walkways near Moorgate must get you at least a kilometre (I haven't measured !).
Under a (sadly now disused) railway, you might pass between the brick piers of the 31 arches of the Hither Green Viaduct, which together are 220 metres in length. You could certainly wade the Quaggy under the central arch. But the views are better from the Green Chain Walk along the top.
I'm struggling to think of any other railway viaducts you can walk ALONG underneath, as most of the Victorian ones have solid transverse walls so that even if they weren't filled with commercial premises, you can only walk across them, not along them.

The Arnos Park viaduct is a lovely structure, which somehow doesn't feel intrusive.
You have two categories here, enclosed and underneath because it passes beneath an obstacle, and underneath something created to carry something else.

So you could have two more, for example underneath something natural like a tree canopy or something artificial like a tube station interchange.
Two long - but probably not record long - subterranean walks. The first is no longer doable, but for a brief time you could walk from the Kings Cross tube entrance in Pentonville Road (now closed) to the new one in King's Boulevard. It would be even longer if you went down and along the Victoria Line platforms on the way. The other is Heathrow: there are some fairly long walks from terminal to bus/tube station and beyond to another terminal, but maybe the effort of having to do it with luggage after a long-haul flight makes it seem longer than it is.
Heathrow is a contender for another reason as well, there are two pedestrian tunnels (one for arrivals, one for departures) connecting the three buildings of Terminal 5. They’re underneath the transit train thing and are a much preferable alternative when the transit is slow, packed or delayed.
Junction 2 techno festival takes place under the Boston Manor Viaduct (and adjacent park) every summer. A great place to dance :)
Not distance-related, is Brixton the only place outside a station where you can walk under two railways at the same time.
The Canary Wharf shopping centres and stations would probably win some category or other.
How about the section of the A4 (Great West Road) that runs underneath the M4?
I think (I think) the pavement beside the Great West Road isn't directly underneath the motorway.
While you might be able to walk under the elevated section of the M4 where it sits on top of the A4, it’s not a proper pavement and you’d be taking a chance dodging traffic.
The elevated section of the M4 through Boston Manor park, on the other hand, provides a dramatic and safe walkway down to the River Brent and the canal, though this space is now often used for pop concerts.
Keen explorers can include this motorway bridge and the older railway viaduct a couple of miles away up the River Brent in the same day - and take in a historic flight of locks and an old triple decker bridge on the way!
cjw24 - Looks like it is just possible at Hinton Road (near Loughborough Junction) and also maybe Linford Street (where the flyover from the Chatham Line, built for Eurostar services, crosses the main lines out of Watreloo
If you care to look much further afield, the PATH network under downtown Toronto has 30 km of passageways, to deal with the cold winter weather. It serves 6 subway stations. I would estimate that the longest point-to-point walk is about 5 km.
Good idea. Made me think of the longer stretch of walking above a pipe/aqueduct/sewer as I once did sections 13-14-15 of the Capital Ring in one go. Section 14 gets you over a Victorian Balzagette sewer for a good while (3 miles I believe) .
The longest distance you can walk underneath something?

How about the flight path of planes landing at Heathrow in a westerly direction.

dg writes: the houses get in the way.
I thought I could find a long stretch of railway to walk underneath from London Bridge station through Borough Market and ending inside the Wheatsheaf on Stoney Street. It looks like a couple of the market entrances don't quite line up well enough with the viaducts to piece the whole thing together but part of it might be a contender.
re "Tramlink along the elevated section in Waddon New Road. "

No it is fenced off - you can walk beside it and see the underside but not walk under it.

Two railways at a time (but cheating) by Brubeck station there is a bridge overmuch Nationa Rail and Tramline run.
In my younger days we used to walk through the disused railway tunnels on the Crystal Palace to Honor Oak route. There were two tunnels , one of which was curved so you couldn’t see the other end and was a bit of a youth challenge to be brave enough to walk it without a torch.. It was years before they blocked the entrances to stop people walking through them.
James Webber - I used to live in Toronto. I would take the metro (aka subway) to Dundas station, and then get off and walk in the PATH from there to Union Station before coming above ground to head to my office at Bay and Queens Quay. 1.8km as the above ground walker would do, but probably a bit longer underground as you have to zig and zag at times.

I believe you can now do the same from College as the PATH has extended north.
I recently checked out underneath the elevated M4 where it goes above the A4, and it is possible, with care, to walk along the central reservation from the Chiswick roundabout until the M4 veers off over buildings towards Boston Manor Park - and you'd clock up a covered distance of about two kilometres.
Agreed. The walk under the elevated M4 wouldn't be especially safe or pleasant, and all the pedestrian infrastructure nudges away from it, but you could walk all 2km while staying beneath the viaduct.










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