ONCE a prominent royal burgh and the administrative centre of the Kingdom of Fife, Cupar remains the quintessential county town.

Nestling in the rolling hills of the Howe of Fife, surrounded by pretty villages and just 10 miles from St Andrews, this characterful town of 9,000 has a plethora of historic buildings and ancient streets and wynds to explore.

It also has some great independent shops, not to mention a number of excellent restaurants on the doorstep, including the first in Scotland to receive a Michelin star.

Historic highlights

Traditionally a market town, Cupar is believed to have grown up around the site of Cupar Castle, seat of the earls of Fife.

At the end of the 13th century, the town was home to an assembly of three estates – clergy, nobility and burghs – organised by Alexander III, a predecessor to the Scottish Parliament.

The town, which sits on the banks of the river Eden, became wealthy and powerful over the centuries, with industries as diverse as farming, brewing, malting, dyeing, tanning, weaving and bookbinding.

Nearby Glenrothes took over the administration of Fife in 1975, but the town is still a centre for the teaching of agriculture, countryside, environmental and golf course management at Elmwood College.

What to do

With its gates, ports and medieval closes, Cupar makes for a fascinating walking tour.

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The mercat cross dates back to 1683 and sits at the old centre of the town between Crossgate and Bonnygate. The ancient mercantile history continues at the same location on the third Saturday of every month with the popular farmer’s market, which takes place from 9am till 1pm. Thirty stallholders offer a wide array of local meats, fish and dairy, fruit and vegetables, homebaking and crafts.

The impressive Preston Lodge, built by the Laird of Airdrie, was erected in 1623 to a design inspired by Culross Palace.

Nearby St Catherine’s Street is home to the Georgian Burgh Chambers and County Buildings, and on Kirkgate sits the Parish Church of Cupar Old, the main structure of which was built in 1745. The bell tower dates back to 1415.

If you need refreshments after all that exploring, pop into the imposing Old Gaol on Station Road, which now operates as Watts bar and restaurant. Nearby Haugh Park has picnic tables and an extensive children's play area.

Local volunteer Guthrie Hutton helps run the nearby Museum and Heritage Centre, situated in the old railway station. “Cupar has a huge history, which I hope we reflect in our exhibits,” he says. “Though if you want to visit this year you’ll need to be quick - our season ends on 11 November.”

Where to eat

Foodies may already know that Cupar punches above its weight when it comes to quality dining. Just off Bonnygate is the delightful Ostler’s Close Restaurant (ostlersclose.co.uk), run by Amanda and Jimmy Graham, serving seasonal Scottish produce cooked with flair and attention.

Just a few yards away is the Courtyard Restaurant, run by German native Hermann Schmidt (thecourtyardcupar.co.uk), which also focuses on local ingredients, though the Bavarian flourishes – and beers – are excellent.

Three miles outside Cupar in Craigrothie is the Kingarroch Inn (kingarrochinngastropub.co.uk), a relaxed gastro pub that has built a strong reputation since opening three years ago. The Sunday lunch alone is worth the trip.

The Michelin-starred Peat Inn (peatinn.co.uk), run by Geoffrey Smeddle, has a global reputation as well as a Michelin star (it received Scotland’s first in the mid-1980s). A rare treat indeed, it is just seven miles outside the town.

If it’s a lunch or afternoon tea in town you’re after, Milly’s Kitchen is just the ticket, offering a full menus of soups, sandwiches salads and quiches (and some of the best scones and muffins for miles). The smoked salmon to go with the scrambled eggs comes straight from St Monans.

The Central Café, meanwhile, does a mean fish supper.

Where to stay

Luxury: Just four miles outside town is Craigsanqhuar (craigsanquhar.com), an 18th century country house hotel and estate set in 36 acres of gardens and woodland. Rooms from £121.

Comfortable: Elegant Ferrymuir Stables B&B (ferrymuirstables.co.uk) is housed in a beautiful 200-year-old block on the western outskirts of Cupar, but still within easy walking distance of the town centre. From £49 per person, per night.

Cosy cottage: This private room in a family home in the town has a kingsize bed and private bathroom. From £38 a night. See Airbnb.co.uk for details.

Grand: Historic Dairsie Castle provides an unusual and surprisingly intimate self-catering holiday home for large groups. Your fairytale awaits. Sleeps 14. From £550 a night. On Airbnb.co.uk.

Where to shop

The town centre has a particularly fine selection of independent shops, as local resident Winifred McEwen points out.

“The Fish Kettle in Ladywynd was established more than 100 years ago and is still an excellent family run shop,” she says. “The herring in dill is particularly good and you can order special requests. I’d also recommend the wide range of cheeses - Scottish, British and European - including a locally-made ewes milk soft cheese. The staff are friendly and helpful.

“Temptations Bakery, on the same street, and the nearby Courtyard Bookshop, are both really good. Pete's Pictures is run by picture framer and performance poet Pete Cura. At the Sign of the Pelican, also in Ladywynd, stocks antique Scottish furniture and much more.

“Artisan butcher Minick provides a terrific service as well as excellent local meat, fruit and vegetables.”

Few, meanwhile, would argue that the fudge doughnuts from Fisher and Donaldson, on Crossgate, are not extremely special - people come from all over Fife and beyond to buy them. The handmade chocolates and pies at this 100-year-old bakery are also delicious.

For gifts, arts and crafts, Maisie and Mac on St Catherine Street is a treasure trove.

Famous faces

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Pioneering photographer and sportswoman Lady Henrietta Gilmour lived just outside Cupar for most of her life. Thought to be the first serious female photographer in Scotland, she also opened up curling to women.

Born in Cupar, Jane Stocks Greig moved to Australia as a teenager and trained as a doctor. She went on to revolutionise public health in the country and was recognised in the Victoria Honour Roll of Women in 2007 and commemorated with a stamp.

Renowned and influential folk singer and musician Rab Noakes was brought up in the town and attended Bell Baxter High.

Things to do nearby

Originally known as Wemyss Hall, Hill of Tarvit, two miles south of Cupar, was transformed by architect Robert Lorimer from a 17th century pile to a one of the most modern and dazzling Edwardian homes of its time, complete with its own golf course, where you can still play with original hickory clubs and balls. It is now run by the National Trust for Scotland.

Take a walk on the wild side at the 55-acre Scottish Deer Centre (tsdc.co.uk), which is home to 13 species of deer as well as bears, lynx, otters, a wolf pack and a variety of raptors. A family favourite, there’s also indoor play and an adventure park.

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Fife Folk Museum (fifefolkmuseum.org) in the nearby village of Ceres offers a fascinating insight into how rural life has shaped Fife for hundreds of years, with a focus on crafts such as weaving and pottery.

Founded in 2014 by former gold caddie Douglas Clement, Kingsbarns Distillery (kingsbarnsdistillery.com), 30 minutes from Cupar, takes visitors on an ongoing journey from Fife-grown barley to dram.

In the coming weeks I'll be going to Stornoway, Auchterarder and Oban. Send your hints and tips for things to do and places to eat, drink and stay, with a few lines about what makes them so memorable, to marianne.taylor@heraldandtimes.co.uk