Arrival at The Chester Grosvenor
The day begins at Chester's most storied address. The Chester Grosvenor has anchored Eastgate Street since 1865, its black-and-white Tudor façade as much a part of Chester as the walls themselves. Check in, take your first coffee in the La Brasserie — or if the occasion warrants it, request the champagne morning menu — and allow the city's particular mood to settle over you.
Two Thousand Years Underfoot
Chester's walls are the most complete Roman walls in Britain, and walking them before the city fully wakes is one of the great pleasures of the place. Begin at the Eastgate Clock — the most photographed timepiece in England after Big Ben — and follow the battlements north. The circuit from the hotel to the cathedral and back to the Roodee takes forty minutes at a leisurely pace, and offers views that would have been familiar to a Roman centurion.
No other city in England preserves its Roman circuit so completely. Walking Chester's walls is to feel history as a physical thing — not behind glass, but under your feet.
— Chester Heritage TrustThe Rows & Chester Cathedral
Chester's medieval Rows are one of the architectural wonders of England: a double tier of half-timbered covered walkways lining Eastgate, Bridge, Northgate and Watergate streets since the 13th century. They are not a reconstruction or a restoration — they are the original medieval fabric, still in commercial use after eight hundred years. Browse the independent jewellers and hatters here; you will want something fitting to wear at the races.
A short detour takes you into Chester Cathedral — not the grand Gothic pile of Lincoln or Ely, but something more intimate: Sandstone Norman arches, the finest medieval choir stalls in England, and an atmosphere of profound quietude. Allow twenty minutes and emerge restored.
The Roodee — Race Day
The walk to the Roodee from the city centre takes no more than twelve minutes, following the walls south-west. The first sight of the course from the embankment — the tight oval cradled in Roman masonry, the stands glittering, the crowd in full summer dress — is one of those views that rewards every step of anticipation.
The Chester Cup and Boodles May Festival are the marquee fixtures; Ladies Day in May and the Midsummer Meeting in July both sell out months in advance. In the Tattersalls Enclosure, the atmosphere is more intimate and informed than at many larger courses. In the County Stand, the view and the setting are peerless. Wherever you are positioned, the racing here — on the tightest flat circuit in Britain — is exhilaratingly close.
In the centre of the course stands a small stone cross — the Rood — marking, by legend, the burial site of a statue of the Virgin Mary. Horse racing has been held on this precise ground since 1539. The Romans used it as a harbour.
— Chester Racecourse Official Record
Sundowners & Supper
After the final race, the walk back through the city is part of the pleasure — Chester at dusk in race season, the streets still warm with the day's event, is a particular kind of English beauty. The choice of where to take a drink before supper reflects the mood: The Bear & Billet on Lower Bridge Street, a magnificent 1664 timber-framed house, offers proper ales and an atmosphere of ancient permanence. Bar Lounge on Northgate Street is lighter and more contemporary, with a terrace that faces the evening light.
For something more informal after a long day at the races, Hickory's Smokehouse on Whitefriars is an outstanding alternative — Tennessee-style slow-smoked barbecue, excellent cocktails, and a lively atmosphere that suits the post-race mood perfectly. For the more formal occasion, Simon Radley remains the finest table in Chester: Michelin-starred, impeccably restrained, and worth every minute of advance planning required to secure a race day reservation.
Where to Stay in Chester
The obvious choice and by some distance the finest room in Chester. AA Five Red Stars, Michelin-starred restaurant on site, and a position on Eastgate Street that cannot be bettered. The suites facing the street have a direct view of the Eastgate Clock. Rates from £280 per night; race day weekends command a premium and sell quickly.
Book The Chester Grosvenor
Six miles south of Chester in its own parkland grounds, the Pulford offers a quieter, spa-centred alternative for those who wish to decompress properly after the races. Four-star with full spa facilities, excellent restaurant, and a level of seclusion the city hotels cannot match. The drive back into Chester for the races takes fifteen minutes.
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