The sign for the Green Man spans the entire width of St John Street, a single beam thrown from one side of the road to the other with the old hotel's name hanging beneath it. Guinness World Records lists it as the longest inn sign in the world, which is the sort of distinction a town either never mentions or mentions constantly. Ashbourne mentions it. The gallows-type sign dates from 1825, made when two inns that faced each other across the street — the Green Man and the Blackmoor's Head — were joined into one. James Boswell ate here in 1777 and pronounced it a very good inn kept by a mighty civil gentlewoman, while Dr Johnson lodged with his friend John Taylor at The Mansion up the road. The pub stopped serving in 2012 and everyone assumed that was that, but it reopened in 2018 with a new bar and restaurant built down the courtyard, in the space last occupied by a brewery.
That reopening tells you something about the town, which has kept an unusual number of its pubs and shops working rather than turning them into second homes. The best of the pubs, by the reckoning of the local CAMRA branch, is Smith's Tavern on St John Street. It has been in the Good Beer Guide continuously since 2013 and named their Pub of the Year in most years since. It is small — a front bar leading back to two further rooms, one with an upright piano and the rear one for darts — and it keeps up to six real ales on at once, with at least one weekend guest chosen from a local or rare brewery. The food goes no further than pork pies from a local artisan butcher, and when those are gone they are gone. The landlords are Mark and Suzie.
The Coach & Horses on Dig Street is the one to head for if you actually want a meal. It has original oak beams, flagstone floors and a log fire, four real ales and food served almost all day. The kitchen does lamb casserole with herby dumplings and cranberry, pork fillet stuffed with black pudding and wrapped in bacon, a Beef and Local Ale pie, and crème brûlée after. There is seating out front and a large paved garden at the back. The George & Dragon, built as a coaching inn in 1710, is the family-and-dog end of things: Cask Marque ales including Dancing Duck, a house beer brewed for them and named Scrappy's nip after the landlord's dog, and a steak and ale pie that reviewers keep calling phenomenal. The chips come in for their own praise, crisp outside and soft in the middle. A short drive out of town on Long Lane, the Horseshoes is the country gastropub — rescued from disrepair by Berkeley Inns in 2015, named Derbyshire's Best Country Pub in 2024, and running a menu of venison cannon, Melton Hall lamb shank and a butternut and sweet potato chowder, alongside more than a hundred gins. Dogs go in the Panel Room, the old areas and the garden. For beer without food there is House of Beer on Church Street, a bottle shop and taproom in a former antique shop with around four hundred world beers, a wall of craft taps, and — since 2024 — two cask handpumps. The Royal Oak sits down by the Henmore Brook, which runs through the middle of the town.
Ashbourne eats well for its size. Café Impromptu on Church Street bakes a White Chocolate and Raspberry Roulade and keeps blankets, treats and water for dogs, whose staff a reviewer noted greet each one with a fuss. f'coffee, tucked in Horse and Jockey Yard, is women-owned and does thick ice-cream milkshakes, homemade pancakes and novelty lattes in charcoal and butterfly-pea, and is known locally for its burger nights. BEAR occupies the old Bennetts department store and turns into a small-plates cocktail bar on Friday and Saturday evenings. Prestons Coffee Bar, at the top of Derby Road beside the garage, was opened by John Preston, formerly a florist and interior specialist, and pours cocktails as well as coffee. For dinner, the Lamplight on Victoria Square is run by two sisters, Pat and Linda, who took it over from their parents; it is a wood-beamed fifteenth-century former coaching inn doing Anglo-French set menus with six to eight choices a course, three of them for a little over twenty pounds.
The shops are where the town does its best work. The Gingerbread Shop sells Ashbourne Gingerbread — soft, raised with soda, made with egg, treacle and ginger — from Spencer's Bakery in the Market Place. Local legend has it the recipe came from a French prisoner of war billeted here during the Napoleonic Wars, said to have been personal chef to General Rochambeau, who surrendered to the English in 1803. The timber-framed building on St John Street where the gingerbread trade began dates from around 1492 and was an inn before it was a bakery. Nigel's Butchers has been on Dig Street since Nigel Brown opened it in April 1982, and the team behind the counter carry more than a hundred and thirty years of butchery between them. Ashbourne Bakehouse in the Market Place, opened by a baker named Lisa, raises most of its bread on its own sourdough starter with no added sugar or fat. Howell and Marsden, a cheese-and-wine deli on the corner of Victoria Square, opened in 2024 named after two Ashbourne wine merchants who traded here in the 1860s. And Church Street is the antiques run — Spurrier-Smith, which keeps vintage motorcycles in the window; Elliots over four floors; and the Ashbourne Antiques Centre with around thirty dealers selling furniture, silver, clocks and light fittings between them. A makers' market takes over the Shawcroft car park on the second and last Saturday of the month.
The reason most people come, though, starts a few hundred yards past the last shop. The Tissington Trail runs thirteen miles from the edge of town to Parsley Hay, following the trackbed of the old Buxton railway, closed in 1954 — traffic-free and mostly flat, shared by walkers, cyclists and horse riders, passing the estate village of Tissington on the way. Ten minutes' drive away is Dovedale, and Ashbourne calls itself the gateway to it with some justification: the limestone ravine draws around a million visitors a year to its stepping stones, a wooded crossing of the River Dove beneath the conical 287-metre hump of Thorpe Cloud. The rock is Carboniferous limestone, roughly 350 million years old, built from the fossils of sea creatures and carved into its pinnacles and caves by glacial meltwater. Lord Byron, writing to the poet Thomas Moore, who lived just outside Ashbourne at Mayfield, put it plainly: "I can assure you there are things in Derbyshire as noble as Greece or Switzerland." The riverside loop from the National Trust car park runs about three and a half miles and takes an easy hour or two, though the stepping stones themselves go under in wet months and you can expect wet feet for the privilege.
There is more within a quarter of an hour's drive than a family could get through in a week. Carsington Water has an eight-mile circuit round the reservoir for walking and cycling, watersports by the hour, a playground and a café with a view. Ilam Park, five miles off, is a National Trust estate on the Manifold where the village was rebuilt in Swiss-chalet style — the Little Switzerland nickname — and where William Congreve is said to have written his first play in a riverside grotto in 1689. In town itself, Ashbourne Park won a Green Flag Award two years running; its splash pads with jets and tipping buckets run May to September, and the Pavilion in the Park, opened in 2022, has refreshments and free toilets. The leisure centre on Clifton Road has a twenty-five-metre pool. At Mapleton, two miles down the Dove, ten teams of three throw themselves thirty feet off the bridge parapet into the freezing river every New Year's Day at noon, then swim to the bank and run to the pub.
The history is worth a paragraph or two once the walking is done. Much of the medieval town burned in 1252, after which the large triangular Market Place was probably laid out; a market charter followed in 1257, and the town now carries over two hundred listed buildings. Domesday recorded it as Esseburne, held directly by King William, with thirteen villagers, nineteen smallholders and one priest, and valued to its lord at one pound, one shilling and twopence. St Oswald's Church, the great building at the west end, is Grade I listed with a needle spire of 212 feet that George Eliot called the finest single spire in England; inside it holds Thomas Banks's 1791 monument to Penelope Boothby, a sleeping child carved from Carrara marble, dead at five and mourned in four languages, and a small brass recording the church's dedication in 1241 that is reckoned the oldest inscribed brass in England. In December 1745 the vanguard of Bonnie Prince Charlie's army came over from Leek and proclaimed his father King at the Market Cross before marching on Derby, and on the retreat the Prince took Ashbourne Hall for his quarters. Catherine Booth, who co-founded the Salvation Army, was born here in 1829. For roughly a hundred and twenty-five years the town's biggest industry was Richard Cooper's corset works, whose Excelsior brand sold under the slogan "a slender figure on a slender purse" until changing fashions closed the factory in the 1980s.
The tradition the town is best known for is Royal Shrovetide Football, played through the streets, fields and the Henmore itself every Shrove Tuesday and Ash Wednesday since at least 1667. The two teams are the Up'ards and the Down'ards, sorted by which side of the brook you were born on, and the goals are millstones set three miles apart at Sturston and Clifton mills. It became "Royal" in 1922 when Princess Mary was given a ball as a wedding gift.
There is no railway now — the line closed in 1954 and its trackbed is the Tissington Trail — so you arrive by the A515 from Buxton or the A52 from Derby, thirteen miles off, with the Swift bus and the 114 running in from the Derby stations. Which leaves the Tunnel Café, which bills itself as the smallest café in Derbyshire and keeps a dog bed and a bowl of water by every table. Every dog that comes in gets a free sausage.
