Ten o'clock, and the town changes gear
Somewhere between half nine and ten, Windsor stops being a restaurant town. Kitchens close, waiters start stacking chairs in the back room, and the High Street, which was busy at six and pleasant at eight, goes quiet enough to hear your own footsteps on the way down Thames Street. Visitors who have only known the town in daylight tend to assume the evening is over. It is not, but it has narrowed.
What is left falls into three kinds of place. There are the old pubs near the castle, which keep ordinary pub hours and do them well. There is a small cluster of later bars at the Peascod Street end of town, which run past the pubs at weekends and often do not midweek. And there are the hotel lounges, which carry on longest of all for the people sleeping upstairs. Knowing which of the three you are heading for saves a walk in the cold to a door that has just been locked.
The old pubs under the walls
The Two Brewers at the top of Park Street is the one people remember: a tiny, low ceilinged pub a few steps from the gates to the Long Walk, with a great deal of character for its size. Around Castle Hill and in the cobbled lanes behind the Guildhall there are several more in the same spirit, small rooms that have been serving drinks under the castle for a very long time.
These keep the hours of a traditional pub. On a weeknight, count on last orders around eleven and a gentle but firm end soon after. At the weekend some run a little later, though none of them is a late bar and none pretends to be. What they offer instead is the best room in the town for the last drink of an ordinary evening, with the walls lit outside and a short walk down to the bridge still ahead of you.
Over the river, the pubs of Eton work to the same rhythm and usually wind down a little earlier. They are lovely at nine and quiet by half ten, and anyone crossing the bridge at eleven in search of a drink will generally end up crossing back.
The Peascod Street end
Peascod Street runs downhill west from the statue at the top of the town, a pedestrian shopping street by day. At its lower end and in the streets running on towards St Leonards Road sit the bars that stay open latest. They are cocktail rooms and bars with music rather than pubs, and on Friday and Saturday nights a few of them keep going past midnight.
This guide does not list them by name, because this corner of town changes hands more often than any other and a name printed today can be a different bar by spring. The shape holds, though. Midweek they often close earlier than their doors suggest, and a Tuesday at half eleven can find the last one pulling its shutters. At the weekend they are livelier, louder and younger than the pubs by the castle. Your companion will usually know which is worth the walk that week, and Etta can check before the evening begins.
The hotel lounges, and who they are for
Once the town has closed, the hotel bars are the real late option. Castle Hotel Windsor, the Harte and Garter and the Macdonald on the High Street, and the Sir Christopher Wren on Thames Street all have bars that keep serving their own guests after the pubs have called time. How late, and whether they still welcome people from outside, depends on the hotel and the night, so a resident has an advantage the rest of the town does not.
That is the strongest argument for staying on the High Street rather than out by the motorway. The lounge downstairs becomes your late bar, with no taxi to wait for and no last train to watch, and if you have taken a room facing the walls the evening can end with the castle in the window. The guide to castle facing rooms explains how to ask for one. As with every hotel on this site, none of these has any arrangement with the desk and none is told anything about a booking.
Getting home, or not needing to
The shuttle from Windsor and Eton Central to Slough thins out before midnight, and the line to Waterloo from Riverside does much the same. Taxis are harder to find at closing time on a Saturday than at any other hour, so book one earlier in the evening if you are not staying in the town. None of this affects your companion, who arranges her own journey home and leaves at the agreed time.
It does affect the length of the booking. A night out that runs from a table at half seven to the last drink at eleven is three and a half hours, so the four hour evening at £900 is the length that fits it, while three hours at £700 suits a night that starts with dinner in the hotel. An hour at £250 in a High Street hotel lounge is fine for a nightcap and nothing more. The fee goes to her in person when she arrives, the figure Etta has written down, and your bar bill is your own.
A late evening that works
Meet in your hotel bar at seven and eat early, at half seven, somewhere on the High Street or down by the river. Walk down Thames Street at nine, when the day visitors have gone, and stand on the bridge for a few minutes looking back at the lit walls. Take the last proper drink in one of the old pubs by ten, before they start calling time, then come back up the hill to the hotel lounge, which will still be serving when the rest of the town is not.
Done in that order, a Windsor evening never runs into a locked door. Done the other way round, starting late and hoping to eat at ten, it usually ends in a hotel lounge anyway, only hungrier.
Who enjoys a late Windsor
Luna spends her evenings at the theatre when she can and will argue about the ending over a last drink for as long as the bar allows. Bianka is at home in small hotel bars and on a High Street that closes early, and she is in no hurry to leave either. Lucy has a weakness for old pubs and cold walks over the bridge, which makes her ideal for the order set out above.
All three are on the early twenties list, and Luna and Bianka are among the curvaceous as well. Who is free on a given night is on who is on.
Cross filed: most of the names on this marker also sit on the early twenties list under by look.