A Weekend in… Rye


The first thing you should do when you arrive in Rye is to make a beeline up the hill it’s built on, to St Mary’s Church. Once there, having admired the stained-glass windows by Sir Edward Burne-Jones, you can pay an old chap £4 to gain access, via a harum-scarum system of steps and ladders, past a set of gigantic brass bells, to the top of the tower. A walkway around the base of the spire gives you a 360-degree rooftopview of the town, with its network of cobbled streets and secret twittens. And of the lay of the land that surrounds it, from the intermittently woody Weald to the north, to the moist, muddy, estuary-veined flatlands that stretch out southwards to the sea.

Once you’re back down among the buildings – many of them medieval, with a smattering of Tudor and Georgian – you get the feeling that Rye is a great-looking old town that is going through an existential revolution. Entrepreneurial (down-from) Londoners are taking advantage of the still-lowish house prices (average in 2022 £398,000; £631,000 for a detached), and regenerating period spaces to accommodate funky new businesses.

It must be galling for Rye’s long-term inhabitants, many of whom are being priced out of their home town. But if you’re after a high concentration of high-end aesthetic and culinary culture, in a beautiful hilltop town that wears its history on its sleeve, then Rye is definitely a good option for a weekend away. Don’t just take our word for it: Conde Nast Traveller paid a visit, for the ‘Destinations’ section of their February edition, and gave a glowing report.


Rye – very possibly from Old English ‘iog’, meaning ‘island’ – has been through many transformations in its long history. It used to be a thriving seaport until violent 13th-century storms, followed by gradual estuary silting and land-reclamation, pushed the shoreline further and further away (it’s now two miles to the mouth of the Rother, at Camber Sands). As one of the strategically important Cinque Ports it enjoyed special status and preferential rights and was much visited by royalty, including Edward III, Charles I, Elizabeth I (who may or may not have enjoyed a pint at the still-extant Mermaid Inn) and George I.

In its long lifetime, the town has had many career changes: it’s been a trading port, a military naval base and shipbuilding centre, a fishing port, a market town, and a tourist centre. There’s still a fishing fleet operating from the riverside quay at the foot of the town, and a thriving farmer’s market every Wednesday, but it is the tourist industry that really drives today’s economy. And it’s clear that the town is shifting its focus towards the trendier and better-moneyed end of the market.


Rye’s higgledy-piggledy Anglo-Saxon street-plan incorporates many corners: you can hardly turn one without coming across an art gallery. The longest standing is Rye Art Gallery on the High Street, much bigger than it looks from the outside (it’s actually two buildings, knocked together in the sixties), which holds a collection of Edward Burra paintings and memorabilia and puts on regular high-quality shows by local artists. Of the many others, the most intriguing is the Peacocke Gallery on Lion Street. Not many tourists ring on the doorbell, as invited: we did last year, and were treated to a guided tour of the artist’s apocalyptic oil-paintings, including the one he was currently working on, in a turpsy back room.

What was originally a 13th-century Augustinian friary on Conduit Hill, the steepest and cobbliest twitten in town, is now a live arts venue, ‘The Monastery’, which hosts occasional events: the weekend we last visited this spring we saw an adaptation of Oscar Wilde’s Salome featuring a troupe of scantily clad dancers. It was an audience-participation number: Venetian masks were provided, and we were served wine and tapas and persuaded to join in the dancing.

Rye Jazz Festival takes place every August, one of the most prestigious in the country: Emeli Sandé headlined in 2021, as we go to press this year’s line-up is still to be announced. There’s also an annual multi-arts festival in the second half of September.

Finally, Lamb House offers a reminder that Rye has been a cultured town for some time. This National Trust-run Georgian townhouse was once owned by the novelist Henry James (and later by EF Benson and Rumer Godden, see pg 76) and many of James’ belongings are on display: the walled garden is a delight.


You can tell that Rye is pleased with itself, as so many of its shops – most of which are independent – include the name of the town in their signage. Wander round, and follow your inclinations, obviously, but we’d particularly recommend three businesses. McCully & Crane is a seriously tasteful art and interiors space selling vintage furniture and contemporary paintings and ceramics. The Paper Place sells gorgeous wrapping paper and other decorated goods from Kashmir. And (more prosaically) The Bargain Box is an old-fashioned family-run newsagent, which will furnish you with all the literature you need about the town, as well as its charmingly clunky long-running community magazine Rye Zone (not to be confused with the more design-led, DFL freebie Ryezine).

Eating and Drinking

For upmarket mezze, try The Union; for great pub grub (including catch of the day chowder) head to The Standard; for a fresh, healthy brunch there’s The Fig café; for pizza and pasta in a friendly atmosphere go to Simply Italian. Boozewise, micropub The Waterworks is a serial winner of CAMRA awards, and doubles up as a junk shop (you can buy the chair you’re sitting on); the more spacious Ypres Castle cares about its beer, and offers a suntrap garden; The Grapevine Champagne & Jazz bar, all dim lights, faded grandeur and redplush upholstery, is a good place for an aperitif, or a nightcap. Finally, The Apothecary is a former chemist which now serves tea and cakes in shabby-chic surroundings, and offers peoplewatching opportunities through its huge leaded bow window, overlooking the high street.


We can thoroughly recommend staying at Tillingham, a vineyard and ‘natural wine’ winery five miles north of Rye, with a bar and restaurant, which also runs twelve extremely modern, extremely comfortable rooms, classily decorated by McCully & Crane (see above). If you can, book in for a wine tasting (their rosé lingers particularly long in the taste-bud memory) or a foraging mission while you’re there. In Rye town centre, we felt extremely well treated at the Hope Anchor, an 18th-century inn boasting four-poster beds and marvellous views, situated at the end of picturesque, cobbly Watch Bell Street, near St Mary’s church.