Shaped by the River Ouse flowing through it, Lewes is a picturesque and free-spirited county town of East Sussex. Hugged by chalky South Downs hills and green pastures, it has charm and history in abundance. Yet, somehow it flies under the radar, overlooked for its gregarious south coast neighbour, Brighton, seven miles north-east.

Local boy Thomas Paine wrote the Rights of Man here, sparking the Age of Enlightenment. Later, the London Bloomsbury set called it their countryside retreat. And next week, its population of just under 100,000 swells for the raucous Lewes Bonfire Celebrations on 4 November – a calendar highlight known as “the Fifth” that’s a year in the making and the only traditional bonfire night of its kind still held in the UK. The town has six bonfire societies, each with its own motto, coloured jumper and cap, and together they form a torch-carrying procession of around 3,000, dragging flaming tar barrels and effigies to the River Ouse.

However, there’s plenty to see and do throughout the rest of the winter. Climb the 11th-century Lewes Castle and Museum (£9 adults) and take in the scene: medieval cobbled streets and twittens (an old Sussex word for alleyway) lined with mostly Georgian buildings housing independent shops, pubs, cafés and restaurants championing local produce.

Getting there and around

Lewes Station is a 15-minute walk from the town centre and is served by Southern trains with routes to London (90 minutes), Brighton (20 minutes) and connections to surrounding towns.

Drop your bags

Trevor House is a superb-value, luxurious bed and breakfast on the high street. The Georgian building dates to 1820 and antique furnishings like four-poster beds fill the three comfy double rooms; the roll-top baths are a big draw. Breakfasts are a generous spread of local organic bread, homemade jam, seasonal berries and fruit. Doubles from £95.

Browse the shops

Lewes is a sweet spot for antique hunting. A cluster of noteworthy shops at the south end of Cliffe High Street includes the vast five-floor Lewes Antiques Centre. Popular since it opened in 1992, is Lewes Flea Market inside an old chapel. At the other end of town, The Fifteenth Century Bookshop is a must for rare and collectable children’s books – and to appreciate its wonky timber façade.

An old Victorian factory called The Needlemakers is home to a warren of indie shops and artisans including Radical Giving. It stocks goods made by social enterprises and independent UK makers, as does Freight HHG on the high street.

Elsewhere, head to Closet & Botts for a vintage-inspired edit, Abby Mosseri for handmade jewellery, Wickle for playful fashion and homewares, and Union Music Store for new and pre-loved vinyl.

On Friday mornings, the Lewes Food Market in the historic market tower and courtyard fills with stalls packed with fresh local farm produce and homemade food made in the Lewes area.

Cosy cafés

Stray downhill from the high street to find Pestle and Mortar, a tiny noodle bar, tearoom and Asian grocery shop. The menu features Thai, Malay, Vietnamese and Taiwanese dishes – steaming bowls of tom yum and laksa soups, fragrant som tum salad with papaya, filling banh mi baguettes and small bites such as gyoza, spicy wings, and prawn crackers. Tables are tucked in the window, amid shelves of packets of noodles and bottles of chilli sauce, and outside in the secluded paved terrace.

Coffee and pastries are available at local takeaway favourite Ground Lewes and drink-in at Flint Owl Bakery.

Rainy day refuges

Historic family-run Harvey’s Brewery, on the River Ouse, has been brewing since 1790. Tours (£12, 90 minutes) reveal the brewing secrets of the musty cellars and end with a tasting.

All tickets on Tuesday are half-price at The Depot cinema. Next to Lewes station, it shows a mix of mainstream and off-beat arthouse films.

Anne of Cleves House (£6.60 adults, under-fives free), dates to the 15th century. Although she never lived in this Tudor home, given to her at the end of her marriage to King Henry VIII in 1541, it’s a good example of period architecture and has a pretty café.

A 20-minute taxi or buses 25 and 39 (Saturdays only, cuckmerebuses.org.uk) takes you to Charleston Farmhouse (from £18.50, under-18s free), the former home of the Bloomsbury Group – Virginia Woolf, Vanessa Bell, Duncan Grant and co. Admire their murals, furniture, paintings, books and textiles, as well as the gardens.

A drink by the fire

In the shadow of the Norman-era Lewes Castle is the 220-year-old Lewes Arms, known for its calendar of eclectic annual events including the World Pea Throwing Championships. Enjoy a pint of Sussex ale and a Sunday roast. Stay a while for a game of Sussex-centric pub game Toad in the Hole – players throw brass coins or “toads” into a hole on the top of a square box on legs.

For locally made small-batch craft beers, Abyss Brewery in the town’s historic brewing area, and Beak Brewery, a short riverside walk away in Cliffe Industrial Estate, both have good selections in sleek surroundings.

Dinner time

The Swan Inn on Southover Street is an unpretentious Lewes favourite for well-priced homemade pub food, while new on the Lewes dining scene is Fork, near the station, serving special-occasion creative (rather than hearty) food. Book ahead for dinner. Two or three-course menus (£47.50 or £57.50) feature local, seasonal produce. Sussex wine is on the list and all spirits are Sussex-made.

Winter walks

If it’s windy, stay low for a stroll around the Lewes Land Nature Reserve. This wild, town-centre spot set on reclaimed railway land is home to four different water habitats including a beautiful spiraling reed bed.

The more formal Southover Grange Gardens, built by William Newton in 1542, are full of pretty paths, colourful flower beds, peaceful benches – and a Mulberry tree thought to be 350 years old.

For a longer hike, take the path up to Mount Caburn and follow an easy route to the pretty village of Glynde, home to the Glyndebourne Opera House. Venture further and you’ll reach the Cuckmere Valley and Seven Sisters.

Three things you might not know about Lewes…

1) In 1638, John Harvard, the Sussex-born founder of the American university, married his wife Ann Sadler at St Michael the Archangel Church, in the parish of South Malling in Lewes.

2) Lewes is the site of the deadliest avalanche in British history. All that remains is a pub named after the disaster, The Snowdrop Inn, and a plaque in a local church to remember those who died.

3) Pells Pool in Lewes, dates to 1850. It’s the oldest, still operating, freshwater outdoor public swimming baths in the UK.