Chesterfield: a welcoming gateway to the Trans Pennine Trail

Destination Chesterfield | Scott Antcliffe Photography

Discover canal-side heritage, wildlife, local landmarks and an easy circular route from one of Derbyshire’s most distinctive towns.

Chesterfield is one of those places where a day on the Trans Pennine Trail can easily become much more than a walk, wheel, ride or cycle. Best known for its famous Crooked Spire, lively market and proud industrial heritage, the town is also a brilliant gateway to one of the Trail’s most varied and enjoyable sections. From Chesterfield, the route follows the beautifully restored Chesterfield Canal towards Staveley, offering an accessible, mostly traffic-free journey through waterside scenery, wildlife-rich spaces and fascinating reminders of the area’s working past.  You can then return to Chesterfield via Poolsbrook Country Park and Brimmington Common – giving you an 11 mile circular route.  Alternatively, from Staveley you can head northwards into Renishaw, Killamarsh and beyond.

Destination Chesterfield | Scott Antcliffe Photography

Why Chesterfield is a great place to start: The Chesterfield spur of the Trans Pennine Trail provides an inviting link into the wider coast-to-coast network. The northern route between Chesterfield and Staveley follows around five miles of the Chesterfield Canal towpath, with easy gradients and a welcoming, multi-user feel. It is ideal for walkers, cyclists, families, wheelchair users and anyone looking for a gentle day out with plenty to see along the way.

For visitors who enjoy a circular route, Chesterfield offers a particularly appealing option. You can follow the canal out towards Staveley, taking in Tapton Lock, Hollingwood Hub and Staveley Basin, before using the Trans Pennine Trail, local bridleways, greenways or public rights of way to loop back towards the town. It is the kind of route that can be enjoyed at a relaxed pace, with coffee stops, wildlife watching and heritage highlights built into the journey.

Following the canal from town to countryside: A natural starting point is Tapton Lock Visitor Centre, just off Lockoford Lane. It’s now run by Chesterfield Canal Trust and is a friendly place to pick up local information, pause for refreshments (7 days a week) and get a feel for the canal before heading out along the towpath. It is also the departure point for the John Varley II passenger boat, making it a great option for visitors who want to experience the canal from the water as well as the Trail. Canal boat trips run regularly but are subject to weather.

Destination Chesterfield | Scott Antcliffe Photography

Further along the canal, Hollingwood Hub is another excellent stop. Home to the Chesterfield Canal Trust, it includes Katey’s Coffee Shop, an information centre and shop, paddlesports hire, accessible facilities, gardens and a welcoming canal-side setting. The Hub is also the base for trips on Madeline and a useful stopping point on a circular walk or ride between Chesterfield and Staveley.

At Staveley Basin, the canal opens out into a peaceful place to pause, look back along the restored waterway and appreciate how much this landscape has changed. It is a good point for walkers and cyclists to turn their outing into a loop, continue towards the wider Trans Pennine Trail network, visit Staveley town centre, or simply enjoy a quieter moment by the water. You can also look at the spectacular new bridge that has been installed along this section of route and the amazing canal restoration works.

More to explore along the way:
The route is not just about getting from A to B. The Chesterfield Canal itself is a visitor attraction, preparing to celebrate its 250th anniversary in 2027. With its rich heritage, restored sections, towpath wildlife and opportunities for walking, cycling, paddlesports and seasonal boat trips, it offers something for everyone. Look out for kingfishers, water voles and waterside plants, and take time to enjoy the contrast between Chesterfield’s busy town centre and the calm of the canal corridor. 

St Mary and All Saints Church | themalcybarkid

Back in Chesterfield, the Crooked Spire of St Mary and All Saints Church is one of the town’s most recognisable landmarks and an easy addition to a Trail visit. The town centre is also home to the historic Chesterfield Market, held on Mondays, Thursdays, Fridays and Saturdays, alongside a range of independent shops, cafés and places to eat, making it a practical and attractive base for anyone planning a day on the Trail.

For those with more time, nearby attractions such as Barrow Hill Roundhouse, Poolsbrook Country Park and the local greenways network add even more variety. Together, they show how the Trail links Chesterfield’s town centre, waterways, former industrial landscapes and green spaces into one joined-up visitor experience.

A Trail day with plenty of reasons to linger
Whether you are looking for a short stroll, a family-friendly cycle, a circular route with a café stop, or a full day discovering canal heritage and Derbyshire countryside, Chesterfield makes an excellent gateway to the Trans Pennine Trail. It is accessible, interesting and full of character — a place where the journey along the Trail is only part of the story.

Mandy – TPT Lead Officer
Date: 14th August, 2026