10 Best Kirkby Stephen Multiday Tours in May 2026

Coast to Coast: St Bees to Kirkby Stephen - 9 Days - May 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

An amazing walking holiday across stunning scenery in the Lakes District. Very well supported by the team, with delightful accommodation, good maps and luggage handling. Thank you!

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hotel, Hostel, Hut, Resort

Age Range

18-99 yrs

Operated in

english

Destinations

London, St Bees, Ennerdale Bridg

London, St Bees, Ennerdale Bridge, Borrowdale, Grasmere, Glenridding, Shap, Orton, Kirkby Stephen

Duration9 days

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Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - 11 Days - May 2026

(2 reviews )

No booking fees

Best price guaranteed

Overall walk was challenging and satisfying.

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Robin Hoods Bay, Kirkby Stephen

Robin Hoods Bay, Kirkby Stephen, Robin Hood’s Bay, Keld, Reeth, Richmond, Danby Wiske, Osmotherley, Clay Bank Top, Blakey, Grosmont

Duration11 days

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Coast to Coast: St Bees to Kirkby Stephen - 8 Days - May 2026

(1 review )

No booking fees

Best price guaranteed

Follow the Coast to Coast Walk from St Bees towards the historic villages and beautiful landscapes of the Yorkshire Dales. Experience the most dramatic section of Wainwright’s legendary Coast to Coast route on this self-guided walking holiday from the Irish Sea at St Bees to the market town of Kirkby Stephen. The western half of the trail showcases some of the most spectacular scenery in northern England, taking you across the rugged heart of the Lake District National Park and into the edge of the Yorkshire Dales. If you're short on time, new to long-distance walking, or prefer to explore the route in manageable stages, this itinerary is an ideal way to sample the best-loved landscapes of the Coast to Coast. It’s also perfect for hikers who simply want the thrill of crossing the Lake District on foot, experiencing the quiet valleys, shimmering lakes, towering peaks and traditional fellside villages. You’ll start your journey by dipping your boots in the Irish Sea at St Bees, then head east with the prevailing wind at your back. The route leads through dramatic valleys such as Ennerdale, Borrowdale, and Patterdale, with the chance to take optional high-level detours to iconic Lakeland summits like Helvellyn. As the Lake District fells give way to the gentler landscapes of the Yorkshire Dales, your walk concludes in Kirkby Stephen, a charming town with rail links and a great place to relax after an inspiring week on the trail. Looking to take things at a gentler pace? Our 9-day version of this trip (trip code WSK) breaks up the longer stage between Shap and Kirkby Stephen, offering a more relaxed alternative. Scroll down to explore all our Coast to Coast walking options.

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hostel, Hotel, Hut, Resort

Age Range

18-99 yrs

Operated in

english

Destinations

London, St Bees, Ennerdale Bridg

London, St Bees, Ennerdale Bridge, Borrowdale, Grasmere, Glenridding, Shap, Kirkby Stephen

Duration8 days

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Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - May 2026

No booking fees

Best price guaranteed

Walk part of the Coast to Coast Walk through the Yorkshire Dales and North York Moors at your own pace. Embark on the eastern half of Alfred Wainwright’s legendary Coast to Coast walk, tracing the route from the rugged Pennines through the Yorkshire Dales and across the heather-covered North York Moors to the dramatic cliffs of the North Sea. Your hike begins near the halfway point of the trail in the Pennines Area of Outstanding Natural Beauty. Cross into the Yorkshire Dales National Park and climb the mystical Nine Standards Rigg. From there, you will follow the scenic River Swale past timeless villages and rolling farmland before arriving in the historic market town of Richmond. The journey continues into the North York Moors National Park, where panoramic vistas and sweeping moorland paths guide you towards the coast. The final stretch leads to Robin Hood’s Bay, where tradition calls for dipping your boots in the North Sea and marking your achievement with a pint, a glass of champagne, or an ice cream on the beach. Along the way, you’ll enjoy the charm of classic northern England; fields of sheep, rolling hills, dry stone walls, friendly local communities, and hearty full English breakfasts. Accommodation is in cosy country hotels, welcoming guesthouses, and traditional pubs—each reflecting the warm hospitality of rural England. For a gentler pace, our 11-day itinerary (trip code WCO) breaks up the final two long stages between Richmond and Blakey Ridge, giving you more time to savour the scenery. Scroll down to explore all our Coast to Coast walking holiday options.

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hotel, Camping

Age Range

18-99 yrs

Operated in

english

Destinations

Robin Hoods Bay, Kirkby Stephen

Robin Hoods Bay, Kirkby Stephen, Keld, Reeth, Richmond, Osmotherley, Blakey, Egton Bridge, Robin Hood’s Bay

Duration9 days

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Kirkby Stephen Tours in May 2026

Get a customized trip to Kirkby Stephen in May 2026

4 Trips in Kirkby Stephen during May 2026 with 8,009 Reviews

4 Trips in Kirkby Stephen during May 2026 with 8,009 Reviews

Coast to Coast: St Bees to Kirkby Stephen - 9 Days - May 2026

Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - 11 Days - May 2026

Coast to Coast: St Bees to Kirkby Stephen - 8 Days - May 2026

Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - May 2026

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Kirkby Stephen Tours in May 2026

Get a customized trip to Kirkby Stephen in May 2026

4 Trips in Kirkby Stephen during May 2026 with 8,009 Reviews

4 Trips in Kirkby Stephen during May 2026 with 8,009 Reviews

Coast to Coast: St Bees to Kirkby Stephen - 9 Days - May 2026

Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - 11 Days - May 2026

Coast to Coast: St Bees to Kirkby Stephen - 8 Days - May 2026

Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - May 2026