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A Crooked Trail Through Chesterfield
I had a brilliant day exploring Chesterfield and some of the surrounding villages, joined by Niall from From Sheffield with Pubs and Chris from Chesterfield Pubs Past & Present. Starting at the Arkwright Arms, we worked our way through New Whittington and Whittington Moor before heading into Chesterfield itself. Along the way it was great to bump into Shaun and Suzie from Chesterfield Great Historic Pub Tours too. There was plenty of history, some fantastic independent pubs and a great variety of beers throughout the day. Another really enjoyable day discovering more of what Chesterfield’s pub scene has to offer.
Chesterfield has a history stretching back more than 2,000 years, with its roots going back to Roman times. It later grew into an important medieval market town, with markets held from at least the 12th century and King John granting a market charter in 1204. The town expanded further during the Industrial Revolution, when coal, iron and engineering became important local industries. Railway pioneer George Stephenson also spent his later years in Chesterfield and is buried here. Today, the town is best known for the famous Crooked Spire of St Mary and All Saints Church, which has become Chesterfield’s most recognisable landmark.
Arkwright Arms
My first visit in Chesterfield was to Arkwright Arms. The Arkwright Arms has been part of Sutton cum Duckmanton for well over 100 years, with records showing it was trading by 1891. Sitting on the road between Chesterfield and Bolsover, it has welcomed everyone from local villagers to travellers and workers from the area’s former coal mines. Over the years it has remained a proper village pub, changing with the times while keeping its traditional character. Today it’s an independent free house with a great reputation for real ale and a warm welcome, making it a popular place for both regulars and visitors to enjoy a pint together.
Inside has a warm, welcoming feel with a choice of different spaces to enjoy. Cosy seating areas feature comfortable bench seating, armchairs and wooden tables, while fireplaces, exposed brickwork and timber details add plenty of character. Soft lighting, large windows and neutral décor keep the pub bright and relaxed, with a separate dining area providing plenty of room for meals. There’s also a dedicated games room with a pool table, making it popular for both a quiet pint and a catch-up with friends. Outside, seating can be found at both the front and rear, with the back terrace offering peaceful countryside views.
Drinks wise on the bar a selection of 5 cask ales, alongside a range of craft keg options to choose from. I went for Bliss Point by Thornbridge Brewery, a hazy pale ale with papaya, passion fruit and guava flavours and a crisp, refreshing finish.
The Lost Lamb
Jumping in a taxi brought us into The Lost Lamb. The Lost Lamb opened on Christmas Eve 2025, bringing a new pub to New Whittington for the first time in many years. It occupies a former High Street shop unit, giving the building a fresh purpose while keeping it at the heart of village life. New Whittington grew rapidly during the 19th century as coal mining and industry expanded around Chesterfield, and the High Street became the centre of the community with its shops, businesses and pubs. Although The Lost Lamb is a modern addition, it continues that long tradition of neighbours meeting, chatting and keeping the village pub culture alive.
Inside has a smart, modern feel with dark green walls, warm lighting and plenty of wood throughout. The compact bar sits to one side, while a mix of tables, padded chairs and high seating provides comfortable spots to relax. A feature fireplace and timber panelling add character, with glossy tiled walls adding a touch of colour and texture. Large front windows bring in plenty of natural light, making the seating by the entrance feel bright and open during the day. Despite its modern finish, the pub still feels cosy, welcoming and somewhere you can happily settle in and spend a few hours.
On the bar a single cask ale and still cider, alongside a rotating range of craft keg lines. A well stocked can and bottle fridge gives you even more choice. I went for Vitória // Mango + Passionfruit by Triple Point Brewing, a fruity sour with juicy mango and passion fruit flavours and a bright, tangy finish.
The Cock & Magpie
Walking around 20 minutes brought me to The Cock & Magpie . The Cock & Magpie has been part of Old Whittington for well over 200 years and is closely linked with one of the village’s most famous landmarks, Revolution House. The original pub on the site was the Cock and Pynot, where leading supporters of the Glorious Revolution met in 1688. Around 1790, that building became a private house and a new pub, the Cock & Magpie, was built just behind it. The Chesterfield Brewery bought the pub in 1884, with major alterations following in 1938 and further extensions during the 1980s. Today it remains a much-loved village local, keeping its long connection with Old Whittington’s remarkable history.
Inside is full of traditional charm, with low ceilings, dark exposed beams and textured walls giving it plenty of character. A series of archways leads through several cosy seating areas, offering everything from upholstered bench seating and comfortable armchairs to classic wooden tables and chairs. Framed pictures, old clocks and other decorative touches add interest without feeling overdone. At the rear, a bright conservatory brings in lots of natural light and provides a more open place to sit, while outside there’s a large paved beer garden with plenty of picnic benches, making it a great spot to enjoy warmer days.
Revolution House in Old Whittington is one of Chesterfield’s most important historic buildings. Originally a 16th-century farmhouse that later became the Cock and Pynot alehouse, it was here in 1688 that three leading supporters of William of Orange met to help plan the Glorious Revolution.
A great selection of 4 cask ales to choose from on the bar including their own house ale, along with a selection of keg options. I went for Cock & Magpie by Little Critters Brewing Company, a pale ale with light citrus hop flavours and a clean, refreshing finish.
The Derby Tup
Jumping on the bus down to Whittington Moor brought me next to The Derby Tup. The Derby Tup has been part of Whittington Moor for well over 150 years. Originally known as the Brunswick Hotel, it was already trading by the 1860s on the corner of Sheffield Road and Shaw Street. In 1983, after Whitbread sold the pub, it was renamed the Derby Tup, taking its name from the famous Derbyshire folk tradition. Since then, it has built a strong reputation as a traditional real ale pub while keeping its friendly local feel. Today it remains an independent favourite, welcoming regulars, visitors and football supporters alike, just a short walk from Chesterfield FC’s stadium.
Inside feels like a proper community local with plenty of character. The main lounge is open and welcoming, with a mix of wooden tables, comfortable bench seating and cosy booths that make it easy to settle in. Soft lighting, traditional wall lamps and large front windows help keep the space bright, while the walls are filled with framed pump clips, local memorabilia and pub signs that give it a personal touch. There’s also a separate snug that’s perfect for a quieter drink, along with a small enclosed outdoor seating area decorated with colourful flowers, offering a pleasant spot to sit outside.
A great selection of 5 cask ales, a still cider and a variety of keg options to choose from. I went for Currant Chaos by The Durham Brewery, a blackcurrant sour with juicy berry flavours and a sharp, refreshing finish.
The Beer Parlour
Just around the corner was The Beer Parlour. The Beer Parlour opened in September 2010, adding a different kind of drinking venue to Whittington Moor. Housed in a former shop on King Street North, it brought the growing micropub-style approach to the area, with the focus on quality beer, friendly conversation and a warm welcome rather than loud entertainment. The building had previously been part of the local shopping parade before being converted into a pub. Since opening, it has built a loyal following among locals, football supporters and real ale enthusiasts, becoming a well-known independent venue that has added something a little different to Whittington Moor’s long pub tradition.
Inside feels warm, welcoming and full of character. Bright mustard-yellow walls, wooden panelling and dark wooden floors give the room a cosy feel, while the long wooden bar is the natural focal point. Traditional shelving behind the bar is filled with glassware, memorabilia and interesting ornaments, adding plenty of personality. A mix of high tables, stools and standard seating offers a choice of places to sit, with large front windows bringing in plenty of natural light during the day. Posters, signs and decorative touches around the room reflect the pub’s character, creating a relaxed atmosphere where it’s easy to settle in for a while.
The bar showcases a great selection of real ales with 8 cask ales to choose from, along with a great selection of keg beers. I went for Trip Hop #7 by Ossett Brewery, a pale ale with bright citrus and tropical fruit flavours and a clean, refreshing finish.
The Chesterfield Arms
Heading back towards the centre brought me to Chesterfield Arms. The Chesterfield Arms has been welcoming customers since 1857, when it opened as the Chesterfield Arms Hotel. Standing on Newbold Road, it has been part of the town’s pub scene for well over 160 years and has remained a popular local through many changes. Today, the pub blends its Victorian roots with a modern approach while keeping a friendly, traditional atmosphere. In 2022 it added its own on-site brewery, Resting Devil, named after Chesterfield’s famous crooked spire legend, giving the historic building a new chapter. It remains a well-known stop for locals and visitors exploring Chesterfield’s pubs.
Inside blends the character of a traditional pub with bright, modern spaces that each have their own feel. Original wood panelling, exposed brickwork and decorative plasterwork sit comfortably alongside stylish lighting, colourful seating and natural timber finishes. Cosy lounges offer comfortable corners to relax, while the larger rooms feel light and open thanks to big windows and high ceilings. Historic photographs, brewery memorabilia and artwork add plenty of interest without feeling cluttered, and visitors can even look through large windows into the on-site brewery. It’s a welcoming pub with lots of different spaces, each full of warmth and character.
A huge line up of 12 cask ales on the bar to choose from, with a number brewed on site, along with a great range of keg options. I went for Tommy Knocker by Resting Devil, a pale ale with light citrus hop flavours and a clean, refreshing finish.
Neptune Beer Emporium
A walk round the corner brought me to The Neptune Beer Emporium. Neptune Beer Emporium at 46 St Helens Street began life as the New Inn in 1862. Before becoming a pub, the building had been used as a Post Office, a haberdashery shop and a chapel of rest for an undertaker. Not long after opening, it was renamed The Neptune, a name that inspired the local nickname “The Neppy.” The pub remained an important part of Chesterfield’s pub scene throughout the 20th century. A full liquor licence was granted in 1951, before it became part of Tennant Brothers of Sheffield and later Whitbread in 1961. In 2015, it was renamed Neptune’s Beer Emporium under new ownership.
Inside has plenty of character, with a series of connected rooms that each have their own style. The front bar has dark wood flooring, padded bench seating and large windows that fill the space with natural light. Colourful pump clips decorate the beams and pillars, while nautical wallpaper, old clocks, framed pictures and maritime touches reflect the pub’s name. The polished wooden bar sits at the heart of the pub, and beyond it are more comfortable seating areas with a mix of tables, chairs and booths. Warm lighting and thoughtful décor create a welcoming atmosphere that encourages you to settle in and relax.
7 cask ales on the bar to choose from in a range of styles, alongside a selection of keg options. I went for Alphito by Neepsend Brew Co., a pale ale with bright citrus and tropical fruit flavours and a clean, refreshing finish.
The Market Pub
Next up in Chesterfield was to The Market Pub. The Market Pub has been part of Chesterfield’s town centre since the 1860s. Originally one of a row of terraced shops on New Square, a former grocery store was taken over in 1864 by Thomas Evinson, who began trading as a wholesale and retail dealer in ales and porters. By 1869, he had expanded into the neighbouring property, creating the Post Office Vaults. Over the years, the pub became known as the New Square Inn, The Market Inn and The Market Tavern, before adopting the name The Market Pub in 1892. It remains a familiar and historic part of Chesterfield’s market area.
Inside is warm, comfortable and full of character. Exposed brick walls, dark timber beams and traditional lighting give it a cosy feel, while colourful wallpaper and framed pictures brighten the space. There’s a mix of button-backed bench seating, wooden tables and comfortable chairs, with plenty of room to relax. The pub is split into a couple of different areas, giving it a nice layout without feeling too large. Everything is clean, well looked after and welcoming, making it an easy place to settle in and enjoy a visit.
During the Second World War, part of The Market Pub was requisitioned by HM Inspectorate of Munitions, reflecting the building’s importance during the war years. An Anderson-style air raid shelter was also built at the rear to provide protection during bombing raids. Anderson shelters, introduced in 1938, were usually constructed from corrugated steel and covered with earth to shield people from blast and shrapnel. Remarkably, the shelter behind The Market Pub still survives today, providing a rare and tangible reminder of the building’s wartime role and Chesterfield’s home front history.
A selection of 6 cask ales to choose from along with ciders and a variety of keg options. I went for Landlord by Timothy Taylor’s Brewery, a classic pale ale with citrus and fruity flavours and a crisp, refreshing finish.
Ye Royal Oak
Next was onto a pub which was closed on my last visit Ye Royal Oak. Ye Royal Oak on The Shambles is widely regarded as Chesterfield’s oldest pub, with records showing it was trading as an inn by the early 18th century. The building is Grade II* listed, and while stories link it to the Knights Templar and even the 12th century, those tales remain part of local legend rather than proven history. What is certain is that the pub has been part of Chesterfield life for hundreds of years, standing beside the historic market in the heart of the old Shambles. After several years closed, it reopened in 2025 following a careful restoration that celebrated its historic character while giving it a fresh new lease of life.
Initially, it served as a rest house for the Knights Templar during the era of the Holy Crusades, and following the medieval period, it was repurposed into two butcher shops. Its location in the heart of the Shambles is fitting, as the term derives from the Anglo-Saxon word “shammels,” which refers to shelves used in slaughterhouses and butcher establishments.
Inside is full of character, with black timber beams, leaded windows and cosy seating areas spread across several rooms. Deep red leather bench seating sits beneath the windows, while stone floors and warm lighting create a welcoming feel throughout. The walls are decorated with old photographs, colourful beer mats and other memorabilia, while hundreds of pump clips cover parts of the ceiling, adding a unique touch. A striking double-height ceiling, stained glass windows and quirky features, including mounted deer heads, make the building feel even more distinctive. It’s a traditional pub where every corner has something different to catch your eye.
A great selection of 6 cask ales to choose from on the bar, alongside a range of keg options to choose from. I went for Clown College by Pentrich Brewing Co, a pale ale with bright citrus and tropical fruit flavours and a clean, refreshing finish.
Society Coffee Shop & Bar
Heading back in the direction of the Railway Station brought me to Society Coffee Shop & Bar. Society opened on Stephenson Place in October 2017, bringing new life to a town centre building with a long retail history. Before Society, the premises was home to Central Perk and the Java Coffee Internet Café, while decades earlier it traded as Mabel Hartley, a well-known milliner and gown shop. The building sits on Stephenson Place, a street named after railway pioneer George Stephenson, who spent his final years in Chesterfield. Since opening, Society has become a popular independent coffee shop by day and bar by night, adding another welcoming stop to Chesterfield’s thriving food and drink scene.
Inside has a bright, welcoming feel that blends modern touches with the character of an older building. The long, narrow room features wooden flooring, panelled walls and a mix of benches, tables and chairs, making it easy to find a comfortable spot. Large glazed front windows let in plenty of natural light, while vintage-style wall lights add a warm glow. Framed artwork, houseplants and the original alcoves give the room plenty of character without feeling cluttered. At the back, the compact bar sits beneath a colourful display of pump clips, adding an eye-catching feature and giving the whole place a relaxed, friendly atmosphere.
3 craft keg lines on the bar to choose from – a Session IPA, Hazy Pale and Lager. I went for Easy by Bianca Road Brewing Co, a pale ale with light citrus and tropical fruit flavours and a clean, refreshing finish.
The Rutland Arms
Located next to the grounds of St Mary’s and All Saints Church is my next stop, The Rutland Arms. Originally the home of Samuel Dutton, who served as Mayor of Chesterfield an impressive eight times between 1818 and 1845, the building was purchased after his death in 1848, enlarged and extensively improved before opening as the Rutland Hotel in 1860. The pub was once much larger but was effectively cut in half when Stephenson Place was widened, leaving the unusual triangular-shaped building seen today. In 1960, Whitbread purchased the pub, and soon afterwards the neighbouring Verger’s House was incorporated into the building, creating the distinctive split-level layout that visitors see today. Standing alongside the famous Crooked Spire, which rises 70 metres high and leans by 9 feet 6 inches after warping over time, The Rutland enjoys one of Chesterfield’s most recognisable locations. Today, the pub is run by The Pub People.
Inside has the feel of a proper traditional pub, with plenty of character spread across its distinctive split-level layout. Dark wooden floors, exposed beams and timber panelling give it a warm, cosy atmosphere, while the different seating areas make it easy to find a quiet corner or settle near the bar. The long polished bar is the heart of the pub, surrounded by high tables, comfortable booths and sturdy wooden furniture. Chalkboards, framed pictures and other interesting touches add personality without feeling cluttered, while large windows bring natural light into the front rooms. It feels welcoming, relaxed and full of charm.
A fantastic line up of 7 cask ales on the bar to choose from, alongside a wide variety of keg options. I went for Ernest by Great Newsome Brewery, a session bitter with malty flavours, stone fruit notes and a smooth, balanced finish.
Saints Bar
My final visit in Chesterfield was to Saints Bar. The former home of Heathcotes and S41, opposite Chesterfield’s famous Crooked Spire on St Mary’s Gate, reopened as Saints Bar in March 2026 following an extensive renovation of the historic Grade II listed building. Dating back to the 1400s, the property is one of the oldest in Chesterfield, with parts rebuilt during the 16th and 17th centuries. After standing empty following the Covid-19 pandemic, it was carefully restored and given a new lease of life. Today, Saints Bar combines centuries of history with a warm, welcoming atmosphere, ensuring this much-loved landmark continues to play its part in Chesterfield’s pub scene.
Inside blends old and new really well. Original stone walls, exposed brickwork and dark wood panelling sit alongside modern décor, giving the building plenty of character without losing its history. The bright glazed roof floods the rear seating area with natural light, while warm pendant lighting keeps it feeling cosy later in the day. A grand piano provides a striking focal point, with wooden floors, comfortable chairs and a mix of open spaces and quieter corners throughout. There is also a small outdoor courtyard, offering another pleasant spot to sit and relax in the heart of the city.
A single cask ales (usually 2) on the bar, along with a great variety of keg options. I went for Jaipur by Thornbridge Brewery, an IPA with citrus and tropical fruit flavours and a crisp, bitter finish.
