High Street has been Cheltenham's backbone throughout its history. Along
it stood the timber-framed houses of the market town, which were gradually
rebuilt or refronted as Cheltenham grew and prospered. It has always been the commercial heart of the town.
Until the early years of the 19th century, when the Regency town began its outward expansion, the town consisted of little more that the High Street and a few lanes and alleys leading into the adjoining fields. The town itself was sometimes called Cheltenham Street. During the town's heyday as a spa, the High Street was a fashionable promenade and contained principal shops and hotels, such as The Plough, the frontage of which is now incorporated into the Regent Arcade.
At the lower west end of the High Street you can find The Brewery, Cheltenham's newest leisure and retail centre. The Lower High Street then continues towards Tewkesbury Road.
At the east end, adjoining London Road the Upper High Street is largely residential, continuing London Road's fine succession of Regency housing. Sandford Park at this side of the High Street provides an excellent place to relax.