Situated on the edge of the Shropshire Hills Area of Outstanding Natural Beauty, Ludlow’s recorded history dates back to 1086 when the castle began to be built, one of many to form a line of defence along the Welsh border and subdue the local Anglo Saxons. 

The ruling family was the Norman De Lacy family, who decided to build a settlement next to the castle. Built in a typical medieval grid fashion, the towns’ original layout can still be clearly seen in the heart of the town.

An extremely pretty town, stroll through the streets of Ludlow and you'll find Instagram-worthy views at every turn, where beautifully maintained houses, dating from medieval times onwards, jostle for being the most picturesque. Ludlow again became popular in the Georgian period, evidenced by the beautiful brick houses – most notably on Broad Street. The town also became well known for its glove making – over 650,000 were made in 1814 alone. 

Today, Ludlow is a bustling, affluent town with a market in the square every Monday, Friday and Saturday throughout the year with Wednesday markets from April to September. Then there’s the multiple festivals of course – whether it’s The Spring Festival, Ludlow Food and Drink Festival, the Medieval Christmas Fayre or more. A particular must, Ludlow’s Food and Drink Festival was the first of its kind in the UK and is a widely-anticipated event each year, taking place each September.

Wander the streets and you’ll discover a fabulous range of independent shops to explore, whether it’s food, clothing, antiques, art or books.

If you’re peckish, the multitude of eateries to choose from is astonishing. With several restaurants in and around Ludlow in the Michelin guide, fine dining is on hand whilst there’s cafes, pubs, tea rooms and international cuisine available too – so something to suit every palate.

Want to eat in your luxury boutique retreat? On the outskirts of the town is Ludlow Farmshop which stocks a fabulously luxurious selection of food and drink, with 80% of it sourced from Shropshire and the surrounding countries. It has a café too.

Places of interest to visit within Ludlow is the ruined castle of course. Dating back to 1086, it has a dominant position above the River Teme with architecture from the Norman, Medieval and Tudor period. St Laurence’s Church, towering over the town, dates back from the Norman times and if you have the puff and energy to climb 135 feet, you’ll be rewarded with excellent views of the town and surrounding villages. Head to the museum on Broad Street which offers an interactive account of Ludlow’s rich history.

A couple of miles north of the town is Ludlow Racecourse, privately owned and dating back to 1725 (but local legend suggests racing has taken place in the area since the 14th century). With at least 16 fixtures a year, check out their website for race days at this friendly racecourse.

Feeling inspired? Take a look at our luxury cottages in Shropshire here and our guide to unique things to do.

Sign up to receive our boutique stories…

Stay connected with retreat magic and be the first to know about our new additions. We promise to only fill your inbox with the dreamiest staycation stories and luxury travel moments.