Leisure & Travel
by Aspect County

Winchelsea – The medieval town

Sitting on a hill-top, cushioned between the historic towns of Rye and Hastings, with far-reaching views of the stunning East Sussex coastline, is Winchelsea. This picturesque former stronghold town, founded in 1288, is the prefect retreat for those wishing to relax and unwind in the surrounds of the English countryside. Once visited it is not difficult to understand why the likes of actor, Henry Irving, and writer, Ford Madox Ford, chose this place as their home. 

Locals claim Winchelsea to be the smallest town in Britain – a fact disputed by the town of Fordwich in Kent; however, you will be pleasantly surprised at its size and the offerings available to visitors passing through. 

Retaining its original medieval setting, including three of the four gate towers, and the largest collection of medieval wine cellars in the country, an ancient town such as this is a treasure trove for history lovers. The town centre is dominated by the part-ruin of St Thomas The Matryr Church, where Spike Milligan’s gravestone can be found, and is surrounded by historic buildings, all telling of the unique history of this cinque-ports town. 

Winchelsea’s location, with Hastings to the west, and Rye a short drive east, makes this the perfect spot for a weekend in the country. The New Inn, an 18th Century coaching inn, is in the heart of the town, offering a charming atmosphere, inglenook fireplaces and character beams. This country-style inn is an ideal starting point for birdwatchers, walkers, and cyclists. In the evenings, a return to the New Inn for a traditional homecooked meal and a pint (or two) of local Sussex ale, will leave you feeling truly relaxed. Double rooms start from £110 per night and include Wi-Fi and breakfast.

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An entire afternoon can be lost exploring the history encased within Winchelsea’s walls. However, there is plenty to do in the surrounding towns and villages, and all within a short distance (by car, foot, and bike): 

The Queens Head: This CAMRA award-winning pub is a must visit. The Queens Head has an excellent reputation for its homemade food and excellent selection of real ales. Featuring in the CAMRA Good Beer Guide for the past 30 years, this traditional 17th century country pub, with sweeping views of the Sussex countryside, is a must visit when staying locally.

WJ Bennett’s, of Rye: This ancient citadel town, designed to protect its citizens from raiders from the sea, reveals its history slowly. From its cobbled streets, nooks and cranny’s, cosy pubs and boutique hotels, Rye has plenty on offer. 

For the Gentleman: WJ Bennett’s of Rye is a menswear boutique specialising in outrageously stylish shirts, designer socks, luxury shoes, and the odd cravat. WJ Bennetts is the place to treat your partner, or yourself (I dare you) to something that will catch a stranger’s eye.

Three Oaks
The Three Oaks Pub: Stepping into this 150-year-old public house, is like walking into history itself. Set deep in the Sussex countryside and along the 1066 walk, it is an ideal rest stop for the keen walker and is adorned with ancient farming objects and brass antiques. This historic pub will not disappoint. Enjoy a pint of local ale, or Sussex wine, while putting your feet up by the open log fire, taking in the sweeping countryside views. www​.thethree​oak​spub​.com

Written by JWR