Events in Chesterfield From 11th May – 17th May 2026

Home · Events in Chesterfield This Week

You can find a range of activities in Chesterfield this week, from skill-building courses to social events. A vocational course at Chesterfield College covers electrical inspection and testing certification. There are regular gatherings at venues like Board & Bean, where the Silent Book Club meets biweekly for quiet reading. The Chesterfield Barnett Observatory opens for stargazing, offering a chance to see the night sky in a dedicated space. Events also take place at Winding Wheel Theatre, which hosts live performances including comedy and musicals. For community connection, check out the Inspire Community Garden or the Grassmoor Community Centre, where a monthly conversation event happens. The town’s heritage as a textile centre is reflected in some workshops, while family-friendly spaces like the Market Hall remain popular. Be mindful of traffic and parking near Cavendish Street, and plan your travel using the Midland Main Line train station or A61 road. A short drive away, Bolsover Castle hosts the Festival of the Arts, showcasing local artists in a historic setting. You’ll also find exhibitions at Doe Lea Resource Centre, exploring digital art and AI. Accessible parking is available at major venues, but parking near the Market Hall can be limited, especially on market days. Check event times and locations before heading out.

Monday 11th May

Level 3 Eal Award in Electrical Installation Inspection Testing Certification…

· Fitness & Outdoors

A vocational course at Chesterfield College covers electrical inspection, testing, and certification.

Friendly Co-working Session For Female Business Owners

· Nightlife & Music

A co-working session for female business owners to connect and support each other in a relaxed setting.

Wednesday 13th May

May Coffee Afternoon With Compassionate Voices at Sorbo

· Food & Drink

A relaxed coffee afternoon at Sorbo Lounge to learn about Compassionate Voices and their empowerment workshops.

Inspire Community Garden

· Inspire Community Garden · Shopping & Markets

A community gardening event focused on social connection and accessible gardening for all.

Thursday 14th May

Connection Café Grassmoor

· Shopping & Markets

A community gathering at Grassmoor Community Centre focused on conversation and compassionate connection.

Silent Book Club

· Board & Bean · Nightlife & Music

The Silent Book Club meets biweekly at Board & Bean in the Annex for quiet reading and discussion.

Comedy Night

· Nightlife & Music

Musical stand-up Richard Morton performs at a comedy night hosted by Ticking Clock Brewing Company.

Friday 15th May

Chesterfield Barnett Observatory Open Evening (Visitors Welcome)

· Chesterfield Barnett Observatory · Nightlife & Music

The Chesterfield Astronomical Society hosts an informal open evening at the Chesterfield Barnett Observatory for visitors to enjoy stargazin

Emma Kenny - Killer Couples

· Winding Wheel Theatre · Nightlife & Music

Comedian Emma Kenny performs her new dark comedy show, Killer Couples, at Winding Wheel Theatre.

New Horizons: Digital Art And ai

· New Barrack Tavern · Culture & Arts

An exhibition exploring digital art and artificial intelligence at Doe Lea Resource Centre in Chesterfield.

I Think he Died of a Tuesday

· English Institute of Sport, Sheffield · Nightlife & Music

Comedy performance titled 'I Think He Died Of A Tuesday' at Bolsover Assembly Rooms in Chesterfield.

Saturday 16th May

Festival of The Arts at Bolsover Castle

· Bolsover Castle · Culture & Arts

Bolsover Castle hosts a Festival of the Arts showcasing local artists, writers, and poets in a historic setting.

Sing The Musicals 2026

· Winding Wheel Theatre · Culture & Arts

A live band and singers perform iconic West End musicals at Winding Wheel Theatre with sing-along lyrics.

Sunday 17th May

Kathryn Roberts & Sean Lakeman

· Nightlife & Music

Acoustic musicians Kathryn Roberts and Sean Lakeman perform at Palterton Village Hall on May 17, 2026.