Chesterfield

Day Trips

Make the most of your day with our curated plans, packed with Chesterfield's hidden gems and unique experiences!

day 1
Exploring the Historic Heart of Chesterfield
morning
:

Start your day with a visit to the iconic Crooked Spire of St. Mary and All Saints Church, where you can marvel at its unique architecture. Afterward, enjoy a leisurely breakfast at a nearby café, soaking in the vibrant local atmosphere. Spend some time wandering through the historic market square, where you can pick up local produce and handmade crafts.

afternoon
:

Take a stroll along the Chesterfield Canal, enjoying the scenic views and perhaps stopping for a picnic by the water. Visit the fascinating Chesterfield Museum to learn more about the town's rich history and heritage. Afterward, enjoy lunch at one of the local pubs, indulging in traditional British fare.

evening
:

As the sun sets, make your way to the bustling Chesterfield town center for an evening of shopping and street entertainment. Try dinner at a renowned local restaurant, sampling regional specialties while soaking in the lively atmosphere. End the night with a relaxing walk around Queen's Park, where you can enjoy the serene environment and twinkling lights.

day 2
Nature Walks and Scenic Views
morning
:

Begin your day with a visit to the beautiful Chatsworth House, where the exquisite gardens and parkland provide an ideal backdrop for a morning stroll. Enjoy breakfast at the estate’s café, taking in the sublime views of the surrounding landscape. Explore the estate’s rich history as you venture through the impressive rooms of the house.

afternoon
:

After your exploration, head to Bakewell, a quaint market town nearby, and indulge in some famous Bakewell pudding for lunch. Spend the afternoon wandering along the River Wye and enjoying the peaceful countryside atmosphere, perfect for relaxation. You could also explore local shops and galleries to discover unique souvenirs.

evening
:

Return to Chesterfield and experience a local theater production at the Pomegranate Theatre, celebrating local talent. Dine at a cozy bistro, where you can enjoy a warm and inviting atmosphere, perfect for reflecting on the day. Conclude your evening with a nightcap at a pub, mingling with locals and enjoying live music.

day 3
Heritage and Culinary Delights
morning
:

Kick off your day with a visit to the Chesterfield Market, one of the largest outdoor markets in the UK, where you can explore stalls brimming with local produce and handmade goods. Grab a tasty breakfast butty from one of the market vendors to fuel your day ahead. Don't forget to visit the local specialty shops for unique products that reflect the region's heritage.

afternoon
:

Join a guided food tour to indulge in Chesterfield's culinary scene, sampling dishes from various local restaurants and eateries. Immerse yourself in the town's history as the guide shares insights about the significance of food in local culture. Spend the afternoon visiting a few of Chesterfield's historic pubs to learn about their remarkable histories.

evening
:

Experience an authentic ‘pub quiz’ night at one of Chesterfield's oldest pubs, engaging with local patrons while testing your trivia skills. Enjoy a hearty dinner featuring traditional British pub fare, perfectly paired with a locally brewed ale. Wrap up the night by chatting with fellow quiz-goers, making new friends along the way.

day 4
Adventure in the Peaks
morning
:

Set out early to explore the stunning landscapes of the Peak District National Park, just a short drive from Chesterfield. Begin your adventure with breakfast at a quaint café in one of the park's charming villages, like Hope or Castleton. Prepare for a day of hiking or cycling by packing snacks and enjoying the fresh country air.

afternoon
:

Choose one of the many trails that weave through the breathtaking scenery, such as the hike to Mam Tor, which offers panoramic views and a sense of achievement. Enjoy a packed lunch amid the serene nature, soaking in the beauty surrounding you. After your hike, explore the local caves in Castleton, which are known for their unique geological formations.

evening
:

Return to Chesterfield for a rejuvenating dinner at a local steakhouse, where you can relive the day’s adventures over hearty dishes. Enjoy the friendly ambience as you share meal recommendations with fellow visitors. Cap off your evening with a leisurely walk through the illuminated town center, appreciating the blend of historical and modern architecture.

day 5
Cultural Immersion and Relaxation
morning
:

Start your morning at the Chesterfield Arts Centre, where you can engage in a creative workshop or simply browse local art exhibitions. Following your artistic excursion, enjoy a leisurely brunch at a nearby café, relishing in the vibrant flavors of local dishes. Don't miss out on the drop-dead gorgeous murals and sculptures throughout the area as you explore.

afternoon
:

Spend the afternoon visiting the Bolsover Castle, a short drive away, where marvelous history and stunning gardens await. Take a guided tour through the castle and its intricate interior, learning about its past as you soak in the views. Afterward, unwind with a coffee at the castle's café, reflecting on the grandeur of it all.

evening
:

Bring your day to a close with a delightful dinner at a farm-to-table restaurant, focusing on fresh, locally-sourced ingredients. Experience the warmth of Chesterfield's hospitality as you indulge in exquisite flavors and beloved dishes. Enjoy your evening by attending a local open mic night or live performance, soaking in the town's rich cultural vibe.

day 6
A Day in the Market Towns
morning
:

Start your day by indulging in a leisurely breakfast at one of Chesterfield’s well-known eateries, later visiting the local bookshops and boutiques for some unique finds. Experience the warmth of the community while enjoying a barista-crafted coffee before setting out to explore the surrounding natural beauty.

afternoon
:

Embark on an exhilarating adventure at a nearby adventure park, engaging in various activities, from zip-lining to climbing. Make sure to take a break for lunch at a nearby café where you can refuel with hearty options. Afterward, enjoy exploring the charming towns nearby and discover the hidden gems they offer.

evening
:

As twilight descends, return to Chesterfield and savor a delightful dinner at an Italian restaurant favored by locals. After your meal, consider catching a live performance at the local art venue, celebrating Chesterfield's artistic talents. Wrap up your day with a relaxing evening walk through the well-lit streets, reflecting on a day filled with joy.

day 7
Local Markets and Historical Landmarks
morning
:

Wake up early and set out to explore the Chesterfield Antiques Centre, a treasure trove for vintage finds and local history enthusiasts. Enjoy breakfast at a nearby café, indulging in traditional pastries while reminiscing over unique items you spotted at the center. Spend some time visiting local bookstores, discovering hidden literary gems.

afternoon
:

Venture to the historic Bolsover Castle for a guided tour, exploring its rich history and stunning architecture. Afterward, enjoy a light lunch at a café down in Bolsover, relishing traditional British cuisine. Spend the late afternoon exploring more of the area’s fascinating historical landmarks.

evening
:

Return to Chesterfield for dinner at a local pub, sampling contemporary interpretations of classic British fare. Engage with friendly locals as you share stories about your day of exploration. Wrap up your evening with a gentle stroll along the canal, enjoying the reflections of the stars above.

day 8
Cultural Heritage and Explore Chesterfield
morning
:

Begin your day with an energizing breakfast at a local café, where you can experience the authentic flavors of Chesterfield. After breakfast, set off to the Chesterfield Heritage Centre, learning about the fascinating past of this vibrant town. Spend some time in the quaint shops selling handmade goods and bakery treats.

afternoon
:

For lunch, head to a nearby eatery that offers a taste of the local cuisine paired with a modern twist. After refueling, take a guided historic walking tour, delving deeper into the tales that shaped Chesterfield. Engage in conversations with the guide about the town's major historical points.

evening
:

As night approaches, visit the iconic Chesterfield Spire again, capturing its beauty as it lights up the evening skyline. Enjoy a fine dining experience at a well-known restaurant, indulging in a multi-course meal. End your evening with a nightcap at a nearby bar, discussing the wonders of the day.

Discover Chesterfield

Read more in our Chesterfield 2025 Travel Guide.

Chesterfield Travel Guide