Daniel O'reilly
Daniel O'Reilly performs a live comedy show at Winding Wheel Theatre in Chesterfield.
THECITYBRIEF
Chesterfield
What's On in Chesterfield – Events This Week & Things To Do
Chesterfield right now: 7 events this week · across 1 venues · 2 categories
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Ever feel like you're hearing about great things happening in Chesterfield, a brilliant find in The Shambles, or an event you'd love, but only weeks after it's over? That's a common problem. Between busy social media feeds and fragmented local groups, the best local happenings get lost. The City Brief solves that. Each week, we select what matters: the markets, views of the Crooked Spire, trails at Poolsbrook, events in Brampton. No endless scrolling. No missing out. Just the information you need, delivered straight to your inbox. Stay connected to Chesterfield in a way that fits your life.
A peek inside recent issues
Events in Chesterfield This Weekend
Mary Poppins Into 90s v 00s
A musical performance reimagines Mary Poppins with 90s and 00s pop culture themes at Chesterfield College Theatre.
Daniel O'reilly: Let's Have it
Comedian Daniel O'Reilly performs his stand-up show 'Let's Have It' at Winding Wheel.
The Legend of Springsteen
The Legend Of Springsteen features a tribute band performing classic Bruce Springsteen hits at Winding Wheel Theatre.
Events in Chesterfield This Week
Encore! - The Studio at Aspire
An encore performance at Winding Wheel Theatre in Chesterfield with studio show details.
Michael Palin: in The Philippines
Michael Palin presents a travel documentary screening in Chesterfield.
Daniel O'reilly
Daniel O'Reilly performs a live comedy show at Winding Wheel Theatre in Chesterfield.
Mary Poppins Into 90s v 00s
A musical performance reimagines Mary Poppins with 90s and 00s pop culture themes at Chesterfield College Theatre.
Daniel O'reilly: Let's Have it
Comedian Daniel O'Reilly performs his stand-up show 'Let's Have It' at Winding Wheel.
The Legend of Springsteen
The Legend Of Springsteen features a tribute band performing classic Bruce Springsteen hits at Winding Wheel Theatre.
Explore Events by Category
Looking for something specific in Chesterfield?
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Upcoming Events by Category
Culture & Arts
Mary Poppins Into 90s v 00s
A theatrical adaptation of Mary Poppins reimagined with 90s and 00s pop culture themes.
Food & Drink
Sixth Form Open Evening
Sixth Form Open Evening at Chesterfield College for prospective students.
Open Evening Showcase - November 2026
Chesterfield College hosts an open evening showcase for prospective students.
Nightlife & Music
The Legend of Springsteen
The Legend Of Springsteen features a tribute band performing classic Bruce Springsteen hits at Winding Wheel Theatre.
Chesterfield Comedy Club
Monthly comedy club night featuring Amuzin Comedy at Real Time Live in Chesterfield.
Shopping & Markets
Chesterfield Artisan Market - November
Chesterfield Artisan Market offers handmade and artisan products in a local retail setting.
Featured Places in Chesterfield
Food & Drink
Cafe NellieCafe Nellie is a cafe on Chatsworth Road in Chesterfield.
View Info →Coffee Bar
St Thomas' Church Coffee BarSt Thomas' Church Coffee Bar is a coffee bar on Chatsworth Road in Chesterfield.
View Info →Specialty Lodging
The Portland HotelThe Portland Hotel is a hotel and pub on West Bars in Chesterfield.
View Info →Chesterfield Places And Events Guides
Things to do in Chesterfield
What's on in Chesterfield covers events from markets and live music to Family & Kids and cultural experiences across town and surrounding areas. Things to do in Chesterfield include exploring the historic town centre with its markets and independent shops, and visiting country parks and heritage sites nearby. Events in Chesterfield take place regularly, with options for all interests, whether you live locally or are visiting. Chesterfield's calendar features Food & Drink events, theatre performances at the Pomegranate Theatre, live music, Shopping & Markets opportunities that have existed for centuries, and family activities in green spaces like Queen's Park and Poolsbrook Country Park. The town centre hosts markets on Monday, Friday, and Saturday with over 200 stalls, while the Market Hall dates back to 1857. You'll find Nightlife & Music in neighbourhoods like Brampton, along with outdoor activities along the canal and in the countryside. Use this site to find events this week and this weekend in Chesterfield, organized by category to help you focus on what interests you. Browse by location to explore what's happening in the town centre, specific neighbourhoods, or near landmarks like the Crooked Spire. The guides help you plan visits to venues and activities across Chesterfield, from a quick look to detailed event information.
Common Chesterfield Questions
### How often are Chesterfield event listings updated? The City Brief updates Chesterfield event listings weekly, ensuring current information about what's happening across town. Our coverage includes regular events like Chesterfield Market, operating Mondays, Fridays, and Saturdays with over 200 stalls, alongside theatre, exhibitions, and activities in these categories: Food & Drink, Family & Kids, Nightlife & Music, Culture & Arts, Fitness & Outdoors, and Shopping & Markets. These listings help you discover events tailored to your interests. ### What are the most popular event categories in Chesterfield? Chesterfield's event scene blends heritage, community, and diverse interests. Popular categories include Culture & Arts, with exhibitions at Hardwick Hall and Bolsover Castle; Nightlife & Music, featuring comedy and live music; and Shopping & Markets, centred around Chesterfield Market and the shops in The Shambles. Food & Drink events showcase local dining, and Fitness & Outdoors activities utilise green spaces including Queen's Park, Poolsbrook Country Park, and the Chesterfield Canal. ### What kinds of events happen in Chesterfield during the week? Throughout the week, Chesterfield hosts events spanning Culture & Arts, Food & Drink, and Fitness & Outdoors. Chesterfield Market operates Mondays, Fridays, and Saturdays. Theatre performances and exhibitions take place around the town centre and at Revolution House. Food events are regular in the Shambles’ independent café scene. The Chesterfield Canal offers walking and cycling, while Queen's Park provides accessible green space. ### How can I find out what's on in Chesterfield this weekend? Browse our This Weekend listings to discover current events across Chesterfield’s seven categories. Filter by Nightlife & Music for comedy clubs or explore Culture & Arts for visits to Bolsover Castle and Hardwick Hall. Shopping & Markets showcases Chesterfield Market, while Fitness & Outdoors highlights activities at Queen's Park and along the Chesterfield Canal. You can also search by venue or neighbourhood like Brampton, or consult our Guides section for recommendations.